Calendar

What’s Happening?

There’s always something to see or do in Highland Park! Check out our calendar to plan your next visit.

 
 

Note: The sponsoring organization for each event is included in the event listing. The City does not sponsor or endorse events listed on the calendar except those attributed to the City of Highland Park. Please direct any questions to the sponsoring organization.

To have your Highland Park event featured, please email Marketing Coordinator Diane Larson.

 

Individual Event Listings

Filtering by: “festivals”
Arbor Day
Apr
25

Arbor Day

Arbor Day

APR. 25 | 9 AM - 11 AM
301 Ravinia Park Rd.


Join the City of Highland Park on Saturday April 25th from 9 AM -11 AM for exhibits, demos, and giveaways to brighten up your home and garden this Spring!

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Ravinia Farmers Market
Jun
3

Ravinia Farmers Market

Ravinia Farmers Market

WEDNESDAYS, JUN. 3 - OCT. 28 | 7 AM - 1 PM
Jens Jensen Park | 540 Roger Williams Ave.


Head to the heart of Highland Park’s Ravinia District for your favorite local farmers market! Shop seasonal produce, meet local vendors, and enjoy live performances throughout the morning.

View Event →
Food Truck Thursdays
Jun
4

Food Truck Thursdays

Food Truck Thursdays

THURSDAYS, JUN. 4 - SEPT. 3 | 4:30 PM - DUSK
Jens Jensen Park | 540 Roger Williams Ave.


Food Truck Thursdays are the spot to be in the Ravinia District this summer, June 4 through September 3, at Jens Jensen Park! Savor fresh flavors from a variety of food trucks, select Highland Park vendors. Enjoy warm summer evenings and dance to great music every Thursday night, 4:30 PM to dusk.

We can’t imagine a better way to spend a summer evening than good friends, good food, and of course, great music.

5 PM - 5:50 PM | Ben Tatar & the Tatar Tots
Children’s Entertainer

6 PM - 8:30 PM | Jared Rabin Band
Classic Rock & Americana

Food Truck Thursdays are presented by the City of Highland Park and the Ravinia District Special Service Area 17 property owners, and are managed by Bensidoun USA. The music for Food Truck Thursdays is coordinated by City contractor, Life Rhythms, Inc., and is co-sponsored by the Highland Park Community Foundation.

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20th Anniversary Bitter Jester Music Festival Preliminary Concert: Night One
Jun
5

20th Anniversary Bitter Jester Music Festival Preliminary Concert: Night One

20th Anniversary

Bitter Jester Music Festival Preliminary Concert - Night One

JUN. 5 | 5:30 PM - 10:30 PM | FREE
Port Clinton Square | 600 Central Ave.


Discover your next favorite band at Bitter Jester, Highland Park's other great music festival! Sponsored by the City of Highland Park, IL, This free, family-friendly concert series has been taking place in Downtown HP annually since 2006. What started as a small "battle of the bands" for local performers has evolved into the nation's largest live festival showcasing emerging artists under the age of 25. Hundreds of performers from all across the nation apply every winter/spring and the festival invites about 40 musical acts from over a dozen states to perform. A "battle of the bands" style event (featuring the top 20% of applicants) has the top acts vying for almost $15,000 in cash and other prizes. With food, craft beer, wine, great coffee, and free parking, the Bitter Jester Music Fest is a must-see event in Downtown Highland Park!

Multiple genres are featured each night with musicians receiving highly detailed feedback from industry professionals in the process. A winner is selected at each of four Preliminary Concerts with four additional "Wild Cards" selected by Festival Producers. Those eight acts then compete head to head at a Grand Finale Concert co-hosted by Nicolas DeGrazia (an Emmy-winning TV director and HP native - the festival's founder) and Peter Sagal (host of "Wait Wait... Don't Tell Me!" on NPR). Come to the Finale for the music and stay to hear Peter interview performers after their sets!

As 101.9 The Mix put it: "It's an incredible concert with a bunch of future headliners!" So check out some of your next favorite bands and be able to say "I saw them when..."

Select Bitter Jester Finalists are chosen to open for national headliners on Ravinia's Carousel Stage and also perform a "Best Of" show at Navy Pier's Beer Garden on Labor Day each year.

Stay tuned for additional details regarding the 2026 Bitter Jester Music Festival.

View Event →
20th Anniversary Bitter Jester Music Festival Preliminary Concert: Night Two
Jun
6

20th Anniversary Bitter Jester Music Festival Preliminary Concert: Night Two

20th Anniversary

Bitter Jester Music Festival Preliminary Concert - Night Two

JUN. 6 | 5:30 PM - 10:30 PM | FREE
Port Clinton Square | 600 Central Ave.


Discover your next favorite band at Bitter Jester, Highland Park's other great music festival! Sponsored by the City of Highland Park, IL, This free, family-friendly concert series has been taking place in Downtown HP annually since 2006. What started as a small "battle of the bands" for local performers has evolved into the nation's largest live festival showcasing emerging artists under the age of 25. Hundreds of performers from all across the nation apply every winter/spring and the festival invites about 40 musical acts from over a dozen states to perform. A "battle of the bands" style event (featuring the top 20% of applicants) has the top acts vying for almost $15,000 in cash and other prizes. With food, craft beer, wine, great coffee, and free parking, the Bitter Jester Music Fest is a must-see event in Downtown Highland Park!

Multiple genres are featured each night with musicians receiving highly detailed feedback from industry professionals in the process. A winner is selected at each of four Preliminary Concerts with four additional "Wild Cards" selected by Festival Producers. Those eight acts then compete head to head at a Grand Finale Concert co-hosted by Nicolas DeGrazia (an Emmy-winning TV director and HP native - the festival's founder) and Peter Sagal (host of "Wait Wait... Don't Tell Me!" on NPR). Come to the Finale for the music and stay to hear Peter interview performers after their sets!

As 101.9 The Mix put it: "It's an incredible concert with a bunch of future headliners!" So check out some of your next favorite bands and be able to say "I saw them when..."

Select Bitter Jester Finalists are chosen to open for national headliners on Ravinia's Carousel Stage and also perform a "Best Of" show at Navy Pier's Beer Garden on Labor Day each year.

Stay tuned for additional details regarding the 2026 Bitter Jester Music Festival.

View Event →
Ravinia Farmers Market
Jun
10

Ravinia Farmers Market

Ravinia Farmers Market

WEDNESDAYS, JUN. 3 - OCT. 28 | 7 AM - 1 PM
Jens Jensen Park | 540 Roger Williams Ave.


Head to the heart of Highland Park’s Ravinia District for your favorite local farmers market! Shop seasonal produce, meet local vendors, and enjoy live performances throughout the morning.

View Event →
Food Truck Thursdays
Jun
11

Food Truck Thursdays

Food Truck Thursdays

THURSDAYS, JUN. 4 - SEPT. 3 | 4:30 PM - DUSK
Jens Jensen Park | 540 Roger Williams Ave.


Food Truck Thursdays are the spot to be in the Ravinia District this summer, June 4 through September 3, at Jens Jensen Park! Savor fresh flavors from a variety of food trucks, select Highland Park vendors. Enjoy warm summer evenings and dance to great music every Thursday night, 4:30 PM to dusk.

We can’t imagine a better way to spend a summer evening than good friends, good food, and of course, great music.

 

5 PM - 5:50 PM | Ravinia Festival’s Jazz Scholars
Student Jazz Band

6 PM - 8:30 PM | Nasty Snacks
Nine-Piece Funk & Soul

Food Truck Thursdays are presented by the City of Highland Park and the Ravinia District Special Service Area 17 property owners, and are managed by Bensidoun USA. The music for Food Truck Thursdays is coordinated by Life Rhythms, Inc., and is co-sponsored by the Highland Park Community Foundation.

View Event →
20th Anniversary Bitter Jester Music Festival Preliminary Concert: Night Three
Jun
12

20th Anniversary Bitter Jester Music Festival Preliminary Concert: Night Three

20th Anniversary

Bitter Jester Music Festival Preliminary Concert - Night Three

JUN. 12 | 5:30 PM - 10:30 PM | FREE
Port Clinton Square | 600 Central Ave.


Discover your next favorite band at Bitter Jester, Highland Park's other great music festival! Sponsored by the City of Highland Park, IL, This free, family-friendly concert series has been taking place in Downtown HP annually since 2006. What started as a small "battle of the bands" for local performers has evolved into the nation's largest live festival showcasing emerging artists under the age of 25. Hundreds of performers from all across the nation apply every winter/spring and the festival invites about 40 musical acts from over a dozen states to perform. A "battle of the bands" style event (featuring the top 20% of applicants) has the top acts vying for almost $15,000 in cash and other prizes. With food, craft beer, wine, great coffee, and free parking, the Bitter Jester Music Fest is a must-see event in Downtown Highland Park!

Multiple genres are featured each night with musicians receiving highly detailed feedback from industry professionals in the process. A winner is selected at each of four Preliminary Concerts with four additional "Wild Cards" selected by Festival Producers. Those eight acts then compete head to head at a Grand Finale Concert co-hosted by Nicolas DeGrazia (an Emmy-winning TV director and HP native - the festival's founder) and Peter Sagal (host of "Wait Wait... Don't Tell Me!" on NPR). Come to the Finale for the music and stay to hear Peter interview performers after their sets!

As 101.9 The Mix put it: "It's an incredible concert with a bunch of future headliners!" So check out some of your next favorite bands and be able to say "I saw them when..."

Select Bitter Jester Finalists are chosen to open for national headliners on Ravinia's Carousel Stage and also perform a "Best Of" show at Navy Pier's Beer Garden on Labor Day each year.

Stay tuned for additional details regarding the 2026 Bitter Jester Music Festival.

View Event →
20th Anniversary Bitter Jester Music Festival Preliminary Concert: Night Four
Jun
13

20th Anniversary Bitter Jester Music Festival Preliminary Concert: Night Four

20th Anniversary

Bitter Jester Music Festival Preliminary Concert - Night Four

JUN. 13 | 5:30 PM - 10:30 PM | FREE
Port Clinton Square | 600 Central Ave.


Discover your next favorite band at Bitter Jester, Highland Park's other great music festival! Sponsored by the City of Highland Park, IL, This free, family-friendly concert series has been taking place in Downtown HP annually since 2006. What started as a small "battle of the bands" for local performers has evolved into the nation's largest live festival showcasing emerging artists under the age of 25. Hundreds of performers from all across the nation apply every winter/spring and the festival invites about 40 musical acts from over a dozen states to perform. A "battle of the bands" style event (featuring the top 20% of applicants) has the top acts vying for almost $15,000 in cash and other prizes. With food, craft beer, wine, great coffee, and free parking, the Bitter Jester Music Fest is a must-see event in Downtown Highland Park!

Multiple genres are featured each night with musicians receiving highly detailed feedback from industry professionals in the process. A winner is selected at each of four Preliminary Concerts with four additional "Wild Cards" selected by Festival Producers. Those eight acts then compete head to head at a Grand Finale Concert co-hosted by Nicolas DeGrazia (an Emmy-winning TV director and HP native - the festival's founder) and Peter Sagal (host of "Wait Wait... Don't Tell Me!" on NPR). Come to the Finale for the music and stay to hear Peter interview performers after their sets!

As 101.9 The Mix put it: "It's an incredible concert with a bunch of future headliners!" So check out some of your next favorite bands and be able to say "I saw them when..."

Select Bitter Jester Finalists are chosen to open for national headliners on Ravinia's Carousel Stage and also perform a "Best Of" show at Navy Pier's Beer Garden on Labor Day each year.

Stay tuned for additional details regarding the 2026 Bitter Jester Music Festival.

View Event →
Ravinia Farmers Market
Jun
17

Ravinia Farmers Market

Ravinia Farmers Market

WEDNESDAYS, JUN. 3 - OCT. 28 | 7 AM - 1 PM
Jens Jensen Park | 540 Roger Williams Ave.


Head to the heart of Highland Park’s Ravinia District for your favorite local farmers market! Shop seasonal produce, meet local vendors, and enjoy live performances throughout the morning.

View Event →
Food Truck Thursdays
Jun
18

Food Truck Thursdays

Food Truck Thursdays

THURSDAYS, JUN. 4 - SEPT. 3 | 4:30 PM - DUSK
Jens Jensen Park | 540 Roger Williams Ave.


Food Truck Thursdays are the spot to be in the Ravinia District this summer, June 4 through September 3, at Jens Jensen Park! Savor fresh flavors from a variety of food trucks, select Highland Park vendors. Enjoy warm summer evenings and dance to great music every Thursday night, 4:30 PM to dusk.

We can’t imagine a better way to spend a summer evening than good friends, good food, and of course, great music.

5 PM - 5:50 PM | Highland Park Players
Local Theater Group

6 PM - 8:30 PM | Nikki O’Neill Band
Blues Rock

Food Truck Thursdays are presented by the City of Highland Park and the Ravinia District Special Service Area 17 property owners, and are managed by Bensidoun USA. The music for Food Truck Thursdays is coordinated by City contractor, Life Rhythms, Inc., and is co-sponsored by the Highland Park Community Foundation.

View Event →
Taste of Highland Park
Jun
19
to Jun 20

Taste of Highland Park

Taste of Highland Park

FRIDAY, JUN. 19 | 5 PM - 10 PM & SATURDAY, JUN. 20 | 3 PM - 10 PM
Port Clinton Square | 600 Central Ave.


More info coming soon!

View Event →
Ravinia Farmers Market
Jun
24

Ravinia Farmers Market

Ravinia Farmers Market

WEDNESDAYS, JUN. 3 - OCT. 28 | 7 AM - 1 PM
Jens Jensen Park | 540 Roger Williams Ave.


Head to the heart of Highland Park’s Ravinia District for your favorite local farmers market! Shop seasonal produce, meet local vendors, and enjoy live performances throughout the morning.

View Event →
Food Truck Thursdays
Jun
25

Food Truck Thursdays

Food Truck Thursdays

THURSDAYS, JUN. 4 - SEPT. 3 | 4:30 PM - DUSK
Jens Jensen Park | 540 Roger Williams Ave.


Food Truck Thursdays are the spot to be in the Ravinia District this summer, June 4 through September 3, at Jens Jensen Park! Savor fresh flavors from a variety of food trucks, select Highland Park vendors. Enjoy warm summer evenings and dance to great music every Thursday night, 4:30 PM to dusk.

We can’t imagine a better way to spend a summer evening than good friends, good food, and of course, great music.

5 PM - 5:50 PM | Jeanie B.!
Children’s Entertainment

6 PM - 8:30 PM | Billy Nixon Band
1950s Rock’n Roll

Food Truck Thursdays are presented by the City of Highland Park and the Ravinia District Special Service Area 17 property owners, and are managed by Bensidoun USA. The music for Food Truck Thursdays is coordinated by City contractor, Life Rhythms, Inc., and is co-sponsored by the Highland Park Community Foundation.

View Event →
20th Anniversary Bitter Jester Music Festival Preliminary Concert: Grand Finale
Jun
27

20th Anniversary Bitter Jester Music Festival Preliminary Concert: Grand Finale

20th Anniversary

Bitter Jester Music Festival Preliminary Concert - Grand Finale

JUN. 27 | 2 PM - 10 PM | FREE
Downtown Highland Park | Second St.


Discover your next favorite band at Bitter Jester, Highland Park's other great music festival! Sponsored by the City of Highland Park, IL, This free, family-friendly concert series has been taking place in Downtown HP annually since 2006. What started as a small "battle of the bands" for local performers has evolved into the nation's largest live festival showcasing emerging artists under the age of 25. Hundreds of performers from all across the nation apply every winter/spring and the festival invites about 40 musical acts from over a dozen states to perform. A "battle of the bands" style event (featuring the top 20% of applicants) has the top acts vying for almost $15,000 in cash and other prizes. With food, craft beer, wine, great coffee, and free parking, the Bitter Jester Music Fest is a must-see event in Downtown Highland Park!

Multiple genres are featured each night with musicians receiving highly detailed feedback from industry professionals in the process. A winner is selected at each of four Preliminary Concerts with four additional "Wild Cards" selected by Festival Producers. Those eight acts then compete head to head at a Grand Finale Concert co-hosted by Nicolas DeGrazia (an Emmy-winning TV director and HP native - the festival's founder) and Peter Sagal (host of "Wait Wait... Don't Tell Me!" on NPR). Come to the Finale for the music and stay to hear Peter interview performers after their sets!

As 101.9 The Mix put it: "It's an incredible concert with a bunch of future headliners!" So check out some of your next favorite bands and be able to say "I saw them when..."

Select Bitter Jester Finalists are chosen to open for national headliners on Ravinia's Carousel Stage and also perform a "Best Of" show at Navy Pier's Beer Garden on Labor Day each year.

Stay tuned for additional details regarding the 2026 Bitter Jester Music Festival.

View Event →
Ravinia Farmers Market
Jul
1

Ravinia Farmers Market

Ravinia Farmers Market

WEDNESDAYS, JUN. 3 - OCT. 28 | 7 AM - 1 PM
Jens Jensen Park | 540 Roger Williams Ave.


Head to the heart of Highland Park’s Ravinia District for your favorite local farmers market! Shop seasonal produce, meet local vendors, and enjoy live performances throughout the morning.

View Event →
Independence Fest
Jul
3

Independence Fest

The Park District of Highland Park presents

Independence Fest

JUL. 3 | 5:30 PM - 9:30 PM
The Preserve of Highland Park - 1207 Park Ave. W.


The Park District of Highland Park invites you to enjoy an evening packed with live entertainment, thrilling rides, carnival games, great food, and exciting activities for all ages! This year’s celebration proudly aligns with America250 to commemorate 250 years of American independence.

Participate in a variety of attractions and games*, get a bite to eat from onsite food & beverage vendors, and dance along to live music from Dancing Queen: An ABBA Salute.

 

*Wristbands are required for games & attractions. Avoid the lines and pre-purchase your wristbands for $10 from Monday, June 15-Friday, July 3 at 3pm at these locations:

  • West Ridge Center - 636 Ridge Road

  • Park Fitness - 1207 Park Ave. W.

  • Highland Park Bank & Trust - 1949 St. Johns Ave.

Wristbands are available on site at The Preserve for $15.

View Event →
Ravinia Farmers Market
Jul
8

Ravinia Farmers Market

Ravinia Farmers Market

WEDNESDAYS, JUN. 3 - OCT. 28 | 7 AM - 1 PM
Jens Jensen Park | 540 Roger Williams Ave.


Head to the heart of Highland Park’s Ravinia District for your favorite local farmers market! Shop seasonal produce, meet local vendors, and enjoy live performances throughout the morning.

View Event →
Food Truck Thursdays: America250 Night
Jul
9

Food Truck Thursdays: America250 Night

Food Truck Thursdays: America250 Theme Night

THURSDAYS, JUN. 4 - SEPT. 3 | 4:30 PM - DUSK
Jens Jensen Park | 540 Roger Williams Ave.


Food Truck Thursdays are the spot to be in the Ravinia District this summer, June 4 through September 3, at Jens Jensen Park! Savor fresh flavors from a variety of food trucks, select Highland Park vendors. Enjoy warm summer evenings and dance to great music every Thursday night, 4:30 PM to dusk.

We can’t imagine a better way to spend a summer evening than good friends, good food, and of course, great music.

5 PM - 5:50 PM | Diamondback Trio
Country

6 PM - 8:30 PM | Blue Rose Band
6-Piece Americana & Country

Food Truck Thursdays are presented by the City of Highland Park and the Ravinia District Special Service Area 17 property owners, and are managed by Bensidoun USA. The music for Food Truck Thursdays is coordinated by City contractor, Life Rhythms, Inc., and is co-sponsored by the Highland Park Community Foundation.

View Event →
Downtown Concert at Port Clinton: Kick Off
Jul
10

Downtown Concert at Port Clinton: Kick Off

Downtown Concerts at Port Clinton: Kick Off

JUL. 10 | 5 PM - 7 PM
Port Clinton Square | 600 Central Ave.


More info coming soon!

View Event →
Ravinia Farmers Market
Jul
15

Ravinia Farmers Market

Ravinia Farmers Market

WEDNESDAYS, JUN. 3 - OCT. 28 | 7 AM - 1 PM
Jens Jensen Park | 540 Roger Williams Ave.


Head to the heart of Highland Park’s Ravinia District for your favorite local farmers market! Shop seasonal produce, meet local vendors, and enjoy live performances throughout the morning.

View Event →
Food Truck Thursdays
Jul
16

Food Truck Thursdays

Food Truck Thursdays

THURSDAYS, JUN. 4 - SEPT. 3 | 4:30 PM - DUSK
Jens Jensen Park | 540 Roger Williams Ave.


Food Truck Thursdays are the spot to be in the Ravinia District this summer, June 4 through September 3, at Jens Jensen Park! Savor fresh flavors from a variety of food trucks, select Highland Park vendors. Enjoy warm summer evenings and dance to great music every Thursday night, 4:30 PM to dusk.

We can’t imagine a better way to spend a summer evening than good friends, good food, and of course, great music.

5 PM - 5:50 PM | Layni Katz Duo
Broadway Pop & Jazz

6 PM - 8:30 PM | Todd Kessler Band
5-Piece Folk Rock

Food Truck Thursdays are presented by the City of Highland Park and the Ravinia District Special Service Area 17 property owners, and are managed by Bensidoun USA. The music for Food Truck Thursdays is coordinated by City contractor, Life Rhythms, Inc., and is co-sponsored by the Highland Park Community Foundation.

View Event →
Downtown Concert at Port Clinton
Jul
17

Downtown Concert at Port Clinton

Downtown Concerts at Port Clinton

JUL. 17 | 6 PM - 8 PM
Port Clinton Square | 600 Central Ave.


More info coming soon!

View Event →
Ravinia Farmers Market
Jul
22

Ravinia Farmers Market

Ravinia Farmers Market

WEDNESDAYS, JUN. 3 - OCT. 28 | 7 AM - 1 PM
Jens Jensen Park | 540 Roger Williams Ave.


Head to the heart of Highland Park’s Ravinia District for your favorite local farmers market! Shop seasonal produce, meet local vendors, and enjoy live performances throughout the morning.

View Event →
Food Truck Thursdays
Jul
23

Food Truck Thursdays

Food Truck Thursdays

THURSDAYS, JUN. 4 - SEPT. 3 | 4:30 PM - DUSK
Jens Jensen Park | 540 Roger Williams Ave.


Food Truck Thursdays are the spot to be in the Ravinia District this summer, June 4 through September 3, at Jens Jensen Park! Savor fresh flavors from a variety of food trucks, select Highland Park vendors. Enjoy warm summer evenings and dance to great music every Thursday night, 4:30 PM to dusk.

We can’t imagine a better way to spend a summer evening than good friends, good food, and of course, great music.

5 PM - 5:50 PM | Anderlik, Church, & Littel
Folk Country

6 PM - 8:30 PM | Aimont Moondance
Celebrating the Music of Van Morrison

Food Truck Thursdays are presented by the City of Highland Park and the Ravinia District Special Service Area 17 property owners, and are managed by Bensidoun USA. The music for Food Truck Thursdays is coordinated by City contractor, Life Rhythms, Inc., and is co-sponsored by the Highland Park Community Foundation.

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America250 at Ravinia Festival - CSO: On the Movies
Jul
24

America250 at Ravinia Festival - CSO: On the Movies

America250 at Ravinia Festival - On the Movies with the Chicago Symphony Orchestra

JUL. 24 | 8 PM
Ravinia Festival | Hunter Pavilion

America250 at Ravinia Festival

Ravinia Festival has been an American institution since 1904; an unofficial summer home of the Midwest where artists come to share and celebrate the joy of live music. For the 250th anniversary of our Declaration of Independence this summer, a wide range of artists, genres, and reflections in American music—from hip-hop and pop to classical and country—will be celebrated across Ravinia Festival concerts, including compositions focused on American themes that honor the history of the nation. 

Chief Conductor Marin Alsop and composer Laura Karpman rack focus on one of America’s leading features in global culture—the movies!—for an evening with the Chicago Symphony Orchestra that illuminates film-music perspectives by and about women. 

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America250 at Ravinia Festival - Chanticleer: Our American Journey
Jul
26

America250 at Ravinia Festival - Chanticleer: Our American Journey

America250 at Ravinia Festival - Chanticleer: Our American Journey

JUL. 26 | 1:30 PM
Ravinia Festival | Martin Theater

America250 at Ravinia Festival

Ravinia Festival has been an American institution since 1904; an unofficial summer home of the Midwest where artists come to share and celebrate the joy of live music. For the 250th anniversary of our Declaration of Independence this summer, a wide range of artists, genres, and reflections in American music—from hip-hop and pop to classical and country—will be celebrated across Ravinia Festival concerts, including compositions focused on American themes that honor the history of the nation. 

The Grammy-winning ensemble Chanticleer traces centuries of musical heritage, exploring spirituals, shape-note songs, barbershop, and vocal jazz alongside bluegrass, folksong, and more as blueprints of contemporary classics. 

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Ravinia Farmers Market
Jul
29

Ravinia Farmers Market

Ravinia Farmers Market

WEDNESDAYS, JUN. 3 - OCT. 28 | 7 AM - 1 PM
Jens Jensen Park | 540 Roger Williams Ave.


Head to the heart of Highland Park’s Ravinia District for your favorite local farmers market! Shop seasonal produce, meet local vendors, and enjoy live performances throughout the morning.

View Event →
Food Truck Thursdays
Jul
30

Food Truck Thursdays

Food Truck Thursdays

THURSDAYS, JUN. 4 - SEPT. 3 | 4:30 PM - DUSK
Jens Jensen Park | 540 Roger Williams Ave.


Food Truck Thursdays are the spot to be in the Ravinia District this summer, June 4 through September 3, at Jens Jensen Park! Savor fresh flavors from a variety of food trucks, select Highland Park vendors. Enjoy warm summer evenings and dance to great music every Thursday night, 4:30 PM to dusk.

We can’t imagine a better way to spend a summer evening than good friends, good food, and of course, great music.

5 PM - 5:50 PM | Brandon Reisdorf Duo
Bluegrass

6 PM - 8:30 PM | Miles Over Mountains
Bluegrass

Food Truck Thursdays are presented by the City of Highland Park and the Ravinia District Special Service Area 17 property owners, and are managed by Bensidoun USA. The music for Food Truck Thursdays is coordinated by City contractor, Life Rhythms, Inc., and is co-sponsored by the Highland Park Community Foundation.

View Event →
Downtown Concert at Port Clinton
Jul
31

Downtown Concert at Port Clinton

Downtown Concerts at Port Clinton

JUL. 31 | 6 PM - 8 PM
Port Clinton Square | 600 Central Ave.


More info coming soon!

View Event →
America250 at Ravinia Festival - CSO: Carlos Simon’s Good News Mass
Jul
31

America250 at Ravinia Festival - CSO: Carlos Simon’s Good News Mass

America250 at Ravinia Festival - Chicago Symphony Orchestra: Carlos Simon’s Good News Mass

JUL. 31 | 7:30 PM
Ravinia Festival | Hunter Pavilion

America250 at Ravinia Festival

Ravinia Festival has been an American institution since 1904; an unofficial summer home of the Midwest where artists come to share and celebrate the joy of live music. For the 250th anniversary of our Declaration of Independence this summer, a wide range of artists, genres, and reflections in American music—from hip-hop and pop to classical and country—will be celebrated across Ravinia Festival concerts, including compositions focused on American themes that honor the history of the nation. 

Chief Conductor Marin Alsop leads the Chicago Symphony Orchestra in Carlos Simon’s Good News Mass, combining African American spirituality and classical music tradition, and dovetails to the American-heartland inspirations in Dvořák’s “New World” Symphony. 

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America250 at Ravinia Festival - Emanuel Ax with CSO: John Adams  & Rachmaninoff
Aug
1

America250 at Ravinia Festival - Emanuel Ax with CSO: John Adams & Rachmaninoff

America250 at Ravinia Festival - Emanuel Ax with Chicago Symphony Orchestra: John Adams & Rachmaninoff

AUG. 1 | 7:30 PM
Ravinia Festival | Hunter Pavilion

America250 at Ravinia Festival

Ravinia Festival has been an American institution since 1904; an unofficial summer home of the Midwest where artists come to share and celebrate the joy of live music. For the 250th anniversary of our Declaration of Independence this summer, a wide range of artists, genres, and reflections in American music—from hip-hop and pop to classical and country—will be celebrated across Ravinia Festival concerts, including compositions focused on American themes that honor the history of the nation. 

Emanuel Ax guests with the Chicago Symphony Orchestra, playing the new Piano Concerto written for him by John Williams. Chief Conductor Marin Alsop also leads music by John Adams and Rachmaninoff’s Symphonic Dances, written shortly before he became an American citizen. 

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America250 at Ravinia Festival - This Land: America in Song
Aug
2

America250 at Ravinia Festival - This Land: America in Song

America250 at Ravinia Festival - This Land: America in Song

AUG. 2 | 5 PM
Ravinia Festival | Hunter Pavilion

America250 at Ravinia Festival

Ravinia Festival has been an American institution since 1904; an unofficial summer home of the Midwest where artists come to share and celebrate the joy of live music. For the 250th anniversary of our Declaration of Independence this summer, a wide range of artists, genres, and reflections in American music—from hip-hop and pop to classical and country—will be celebrated across Ravinia Festival concerts, including compositions focused on American themes that honor the history of the nation. 

Ted Sperling hosts and conducts “This Land,” traversing two centuries-plus of popular music across U.S. history with the Chicago Symphony Orchestra—Stephen Foster gems, Sam Cooke and Bob Dylan anthems, songs from stage and screen, and more.

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Ravinia Farmers Market
Aug
5

Ravinia Farmers Market

Ravinia Farmers Market

WEDNESDAYS, JUN. 3 - OCT. 28 | 7 AM - 1 PM
Jens Jensen Park | 540 Roger Williams Ave.


Head to the heart of Highland Park’s Ravinia District for your favorite local farmers market! Shop seasonal produce, meet local vendors, and enjoy live performances throughout the morning.

View Event →
Food Truck Thursdays
Aug
6

Food Truck Thursdays

Food Truck Thursdays

THURSDAYS, JUN. 4 - SEPT. 3 | 4:30 PM - DUSK
Jens Jensen Park | 540 Roger Williams Ave.


Food Truck Thursdays are the spot to be in the Ravinia District this summer, June 4 through September 3, at Jens Jensen Park! Savor fresh flavors from a variety of food trucks, select Highland Park vendors. Enjoy warm summer evenings and dance to great music every Thursday night, 4:30 PM to dusk.

We can’t imagine a better way to spend a summer evening than good friends, good food, and of course, great music.

5 PM - 5:50 PM | Lucky Pickers
Folk

6 PM - 8:30 PM | Big Sadie
Western Swing

Food Truck Thursdays are presented by the City of Highland Park and the Ravinia District Special Service Area 17 property owners, and are managed by Bensidoun USA. The music for Food Truck Thursdays is coordinated by City contractor, Life Rhythms, Inc., and is co-sponsored by the Highland Park Community Foundation.

View Event →
Downtown Concert at Port Clinton
Aug
7

Downtown Concert at Port Clinton

Downtown Concerts at Port Clinton

AUG. 7 | 6 PM - 8 PM
Port Clinton Square | 600 Central Ave.


More info coming soon!

View Event →
America250 at Ravinia Festival - America the Elusive
Aug
8

America250 at Ravinia Festival - America the Elusive

America250 at Ravinia Festival - This Land: America in Song

AUG. 8 | 1:30 PM
Ravinia Festival | Bennett Gordon Hall

America250 at Ravinia Festival

Ravinia Festival has been an American institution since 1904; an unofficial summer home of the Midwest where artists come to share and celebrate the joy of live music. For the 250th anniversary of our Declaration of Independence this summer, a wide range of artists, genres, and reflections in American music—from hip-hop and pop to classical and country—will be celebrated across Ravinia Festival concerts, including compositions focused on American themes that honor the history of the nation. 

Ravinia Festival’s Steans Institute performance-study fellowship program for emerging professional classical singers presents an afternoon concert featuring a kaleidoscope of musical impressions of America from diverse times, places, and viewpoints, including music by Ives, Weill, Puccini, Britten, Montsalvatge, Dvořák, and Rameau.

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Ravinia Farmers Market
Aug
12

Ravinia Farmers Market

Ravinia Farmers Market

WEDNESDAYS, JUN. 3 - OCT. 28 | 7 AM - 1 PM
Jens Jensen Park | 540 Roger Williams Ave.


Head to the heart of Highland Park’s Ravinia District for your favorite local farmers market! Shop seasonal produce, meet local vendors, and enjoy live performances throughout the morning.

View Event →
Food Truck Thursdays
Aug
13

Food Truck Thursdays

Food Truck Thursdays

THURSDAYS, JUN. 4 - SEPT. 3 | 4:30 PM - DUSK
Jens Jensen Park | 540 Roger Williams Ave.


Food Truck Thursdays are the spot to be in the Ravinia District this summer, June 4 through September 3, at Jens Jensen Park! Savor fresh flavors from a variety of food trucks, select Highland Park vendors. Enjoy warm summer evenings and dance to great music every Thursday night, 4:30 PM to dusk.

We can’t imagine a better way to spend a summer evening than good friends, good food, and of course, great music.

5 PM - 5:50 PM | Wincanton
Local Jam Folk Duo

6 PM - 8:30 PM | Railheart
Ultimate Grateful Dead Tribute

Food Truck Thursdays are presented by the City of Highland Park and the Ravinia District Special Service Area 17 property owners, and are managed by Bensidoun USA. The music for Food Truck Thursdays is coordinated by City contractor, Life Rhythms, Inc., and is co-sponsored by the Highland Park Community Foundation.

View Event →
Downtown Concert at Port Clinton
Aug
14

Downtown Concert at Port Clinton

Downtown Concerts at Port Clinton

AUG. 14 | 6 PM - 8 PM
Port Clinton Square | 600 Central Ave.


More info coming soon!

View Event →
Ravinia Farmers Market
Aug
19

Ravinia Farmers Market

Ravinia Farmers Market

WEDNESDAYS, JUN. 3 - OCT. 28 | 7 AM - 1 PM
Jens Jensen Park | 540 Roger Williams Ave.


Head to the heart of Highland Park’s Ravinia District for your favorite local farmers market! Shop seasonal produce, meet local vendors, and enjoy live performances throughout the morning.

View Event →
Food Truck Thursdays - 90s Theme Night
Aug
20

Food Truck Thursdays - 90s Theme Night

Food Truck Thursdays - 90s Theme Night

THURSDAYS, JUN. 4 - SEPT. 3 | 4:30 PM - DUSK
Jens Jensen Park | 540 Roger Williams Ave.


Food Truck Thursdays are the spot to be in the Ravinia District this summer, June 4 through September 3, at Jens Jensen Park! Savor fresh flavors from a variety of food trucks, select Highland Park vendors. Enjoy warm summer evenings and dance to great music every Thursday night, 4:30 PM to dusk.

We can’t imagine a better way to spend a summer evening than good friends, good food, and of course, great music.

5 PM - 5:50 PM | Laura Glyda
90s Folk

6 PM - 8:30 PM | Ren Patrick & the Players
90s Pop & Rock

Food Truck Thursdays are presented by the City of Highland Park and the Ravinia District Special Service Area 17 property owners, and are managed by Bensidoun USA. The music for Food Truck Thursdays is coordinated by City contractor, Life Rhythms, Inc., and is co-sponsored by the Highland Park Community Foundation.

View Event →
Downtown Concert at Port Clinton
Aug
21

Downtown Concert at Port Clinton

Downtown Concerts at Port Clinton

AUG. 21 | 6 PM - 8 PM
Port Clinton Square | 600 Central Ave.


More info coming soon!

View Event →
Vintage Car Show
Aug
22

Vintage Car Show

Vintage Car Show

AUG. 22 | 12 PM - 4 PM
St. Johns North Parking Lot | 525 Central Ave.


More info coming soon!

View Event →
Ravinia Farmers Market
Aug
26

Ravinia Farmers Market

Ravinia Farmers Market

WEDNESDAYS, JUN. 3 - OCT. 28 | 7 AM - 1 PM
Jens Jensen Park | 540 Roger Williams Ave.


Head to the heart of Highland Park’s Ravinia District for your favorite local farmers market! Shop seasonal produce, meet local vendors, and enjoy live performances throughout the morning.

View Event →
Food Truck Thursdays
Aug
27

Food Truck Thursdays

Food Truck Thursdays

THURSDAYS, JUN. 4 - SEPT. 3 | 4:30 PM - DUSK
Jens Jensen Park | 540 Roger Williams Ave.


Food Truck Thursdays are the spot to be in the Ravinia District this summer, June 4 through September 3, at Jens Jensen Park! Savor fresh flavors from a variety of food trucks, select Highland Park vendors. Enjoy warm summer evenings and dance to great music every Thursday night, 4:30 PM to dusk.

We can’t imagine a better way to spend a summer evening than good friends, good food, and of course, great music.

5 PM - 5:50 PM | Petra van Nuis Duo
Jazz Duo

6 PM - 8:30 PM | Bumpus
9-Piece Funk Band

Food Truck Thursdays are presented by the City of Highland Park and the Ravinia District Special Service Area 17 property owners, and are managed by Bensidoun USA. The music for Food Truck Thursdays is coordinated by City contractor, Life Rhythms, Inc., and is co-sponsored by the Highland Park Community Foundation.

View Event →
Ravinia Farmers Market
Sep
2

Ravinia Farmers Market

Ravinia Farmers Market

WEDNESDAYS, JUN. 3 - OCT. 28 | 7 AM - 1 PM
Jens Jensen Park | 540 Roger Williams Ave.


Head to the heart of Highland Park’s Ravinia District for your favorite local farmers market! Shop seasonal produce, meet local vendors, and enjoy live performances throughout the morning.

View Event →
Food Truck Thursdays
Sep
3

Food Truck Thursdays

Food Truck Thursdays

THURSDAYS, JUN. 4 - SEPT. 3 | 4:30 PM - DUSK
Jens Jensen Park | 540 Roger Williams Ave.


Food Truck Thursdays are the spot to be in the Ravinia District this summer, June 4 through September 3, at Jens Jensen Park! Savor fresh flavors from a variety of food trucks, select Highland Park vendors. Enjoy warm summer evenings and dance to great music every Thursday night, 4:30 PM to dusk.

We can’t imagine a better way to spend a summer evening than good friends, good food, and of course, great music.

5 PM - 5:30 PM | Mr. Dave
Children’s Entertainment

5:45 PM - 8 PM | WHKW (feat. members of Family Groove Company & 56 Hope Road)
Covering Classics by CSNY & Other Laurel Canyon Favorites

Food Truck Thursdays are presented by the City of Highland Park and the Ravinia District Special Service Area 17 property owners, and are managed by Bensidoun USA. The music for Food Truck Thursdays is coordinated by City contractor, Life Rhythms, Inc., and is co-sponsored by the Highland Park Community Foundation.

View Event →
Downtown Concert at Port Clinton
Sep
4

Downtown Concert at Port Clinton

Downtown Concerts at Port Clinton

SEPT. 4 | 6 PM - 8 PM
Port Clinton Square | 600 Central Ave.


More info coming soon!

View Event →
Ravinia Farmers Market
Sep
9

Ravinia Farmers Market

Ravinia Farmers Market

WEDNESDAYS, JUN. 3 - OCT. 28 | 7 AM - 1 PM
Jens Jensen Park | 540 Roger Williams Ave.


Head to the heart of Highland Park’s Ravinia District for your favorite local farmers market! Shop seasonal produce, meet local vendors, and enjoy live performances throughout the morning.

View Event →
Downtown Concert at Port Clinton
Sep
11

Downtown Concert at Port Clinton

Downtown Concerts at Port Clinton

SEPT. 11 | 6 PM - 8 PM
Port Clinton Square | 600 Central Ave.


More info coming soon!

View Event →
Ravinia Farmers Market
Sep
16

Ravinia Farmers Market

Ravinia Farmers Market

WEDNESDAYS, JUN. 3 - OCT. 28 | 7 AM - 1 PM
Jens Jensen Park | 540 Roger Williams Ave.


Head to the heart of Highland Park’s Ravinia District for your favorite local farmers market! Shop seasonal produce, meet local vendors, and enjoy live performances throughout the morning.

View Event →
Downtown Concert at Port Clinton
Sep
18

Downtown Concert at Port Clinton

Downtown Concerts at Port Clinton

SEPT. 18 | 6 PM - 8 PM
Port Clinton Square | 600 Central Ave.


More info coming soon!

View Event →
Ravinia Farmers Market
Sep
23

Ravinia Farmers Market

Ravinia Farmers Market

WEDNESDAYS, JUN. 3 - OCT. 28 | 7 AM - 1 PM
Jens Jensen Park | 540 Roger Williams Ave.


Head to the heart of Highland Park’s Ravinia District for your favorite local farmers market! Shop seasonal produce, meet local vendors, and enjoy live performances throughout the morning.

View Event →
Downtown Concert at Port Clinton: Finale
Sep
25

Downtown Concert at Port Clinton: Finale

Downtown Concerts at Port Clinton: Finale & Scarecrow Trail

SEPT. 25 | 4 PM - 8 PM
Port Clinton Square | 600 Central Ave.


More info coming soon!

View Event →
Oktoberfest
Sep
26

Oktoberfest

Oktoberfest

SEPT. 26 | 4 PM - 8 PM
Jens Jensen Park | 540 Roger Williams Ave.


More info coming soon!

View Event →
Ravinia Farmers Market
Sep
30

Ravinia Farmers Market

Ravinia Farmers Market

WEDNESDAYS, JUN. 3 - OCT. 28 | 7 AM - 1 PM
Jens Jensen Park | 540 Roger Williams Ave.


Head to the heart of Highland Park’s Ravinia District for your favorite local farmers market! Shop seasonal produce, meet local vendors, and enjoy live performances throughout the morning.

View Event →
Ravinia Farmers Market
Oct
7

Ravinia Farmers Market

Ravinia Farmers Market

WEDNESDAYS, JUN. 3 - OCT. 28 | 7 AM - 1 PM
Jens Jensen Park | 540 Roger Williams Ave.


Head to the heart of Highland Park’s Ravinia District for your favorite local farmers market! Shop seasonal produce, meet local vendors, and enjoy live performances throughout the morning.

View Event →
Stews & Brews
Oct
10

Stews & Brews

Stews & Brews

OCT. 10 | 4 PM - 9 PM
Port Clinton Square | 600 Central Ave.


More info coming soon!

View Event →
Ravinia Farmers Market
Oct
14

Ravinia Farmers Market

Ravinia Farmers Market

WEDNESDAYS, JUN. 3 - OCT. 28 | 7 AM - 1 PM
Jens Jensen Park | 540 Roger Williams Ave.


Head to the heart of Highland Park’s Ravinia District for your favorite local farmers market! Shop seasonal produce, meet local vendors, and enjoy live performances throughout the morning.

View Event →
Ravinia Farmers Market
Oct
21

Ravinia Farmers Market

Ravinia Farmers Market

WEDNESDAYS, JUN. 3 - OCT. 28 | 7 AM - 1 PM
Jens Jensen Park | 540 Roger Williams Ave.


Head to the heart of Highland Park’s Ravinia District for your favorite local farmers market! Shop seasonal produce, meet local vendors, and enjoy live performances throughout the morning.

View Event →
Ravinia Farmers Market
Oct
28

Ravinia Farmers Market

Ravinia Farmers Market

WEDNESDAYS, JUN. 3 - OCT. 28 | 7 AM - 1 PM
Jens Jensen Park | 540 Roger Williams Ave.


Head to the heart of Highland Park’s Ravinia District for your favorite local farmers market! Shop seasonal produce, meet local vendors, and enjoy live performances throughout the morning.

View Event →
Holiday Lighting
Nov
21

Holiday Lighting

Holiday Lighting

NOV. 21 | 4 PM - 6 PM
Port Clinton Square | 600 Central Ave.


More info coming soon!

View Event →

Holiday Lighting
Nov
22

Holiday Lighting

Holiday Lighting

NOV. 22 | 4 PM - 6 PM
Port Clinton Square | 600 Central Ave.

Join the City on November 22 for a revamped and enhanced Holiday Lighting, featuring an updated tree and menorah display. The fun will take place at Port Clinton Square (600 Central Ave.) between 4 PM – 6 PM.

Welcome Hanukkah Harry and Santa Claus beginning at 4 PM, with a special Highland Park Fire Department escort. Meet them both, share what’s on your holiday wish list, find out if you’re on the nice list, and take a photo!

Stroll around Port Clinton Square and meet Anna and Elsa from Frozen, enjoy the Frozen Robin Carolers, visit a facepainter for a festive holiday look, grab some complementary popcorn and cocoa, and enjoy the holiday cheer while DJ Julian Emcees and spins your favorite holiday tunes.

The Highland Park High School Choir will perform from 4:30 PM - 4:45 PM, just before Mayor Nancy Rotering waves the magic wand and the lights go on! Be sure to pop into one or more of the holly jolly photo vignettes throughout the plaza - they’re perfect for family photos and Instagram.

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Ravinia Farmers Market
Oct
29

Ravinia Farmers Market

Ravinia Farmers Market

Wednesdays, June 4 - October 29 | 7 AM - 1 PM
Jens Jensen Park | 540 Roger Williams Ave.


Head to the heart of Highland Park’s Ravinia District for your favorite local farmers market! Shop seasonal produce, meet local vendors, and enjoy live performances throughout the morning.

ENTERTAINMENT

  • 9 AM – 10 AM | Jazzman Jeff

  • 10:30 AM – 11:30 AM | Pierce Crask

  • 12 PM – 1 PM | Albie Powers & Friends

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Día de los Muertos Week
Oct
25
to Nov 2

Día de los Muertos Week

Día de los Muertos Week

OCT. 25 - NOV. 2


Día de los Muertos Week returns for a second year to Downtown Highland Park October 25 - November 2, 2025. Take part in a week-long celebration featuring various workshops, cultural experiences, and installations.

Día de los Muertos is a Mexican holiday, held November 1 & 2, honoring the lives of deceased loved ones.

Día de los Muertos Week will kick off on October 25 with a free community celebration from 3 PM – 5 PM at the Memorial Park Gazebo (405 Prospect Ave.), where a large-scale Ofrenda (altar) will serve as the anchor of the festivities. This vibrant celebration of life will continue throughout the week with cultural experiences ranging from Latino food and drink tastings and cooking demos to craft workshops and performances.

A limited number of experience passes are available for $35 in advance ($45 at the kick-off event), offering access to wine and tequila tastings, pan de muerto baking, sugar skull decorating, papel picado workshops, cempasúchil flower arranging, VIP admission to the Catrina fashion show, and more.

Día de los Muertos Week will conclude with a Catrina fashion show and contest on November 2 from 2 PM - 4 PM. Community members are invited to share their own interpretations of “La Catrina” through elegant costumes, elaborate makeup, and floral headdresses.

View Event →
Ravinia Farmers Market
Oct
22

Ravinia Farmers Market

Ravinia Farmers Market

Wednesdays, June 4 - October 29 | 7 AM - 1 PM
Jens Jensen Park | 540 Roger Williams Ave.


Head to the heart of Highland Park’s Ravinia District for your favorite local farmers market! Shop seasonal produce, meet local vendors, and enjoy live performances throughout the morning.

ENTERTAINMENT

  • 9 AM – 10 AM | Jazzman Jeff

  • 10:30 AM – 11:30 AM | Pierce Crask

  • 12 PM – 1 PM | Albie Powers & Friends

View Event →
Ravinia Farmers Market
Oct
15

Ravinia Farmers Market

Ravinia Farmers Market

Wednesdays, June 4 - October 29 | 7 AM - 1 PM
Jens Jensen Park | 540 Roger Williams Ave.


Head to the heart of Highland Park’s Ravinia District for your favorite local farmers market! Shop seasonal produce, meet local vendors, and enjoy live performances throughout the morning.

ENTERTAINMENT

  • 9 AM – 10 AM | Jazzman Jeff

  • 10:30 AM – 11:30 AM | Pierce Crask

  • 12 PM – 1 PM | Albie Powers & Friends

View Event →
Stews & Brews
Oct
11

Stews & Brews

Stews & Brews

OCT. 11 | 5 PM - 9 PM
PORT CLINTON SQUARE | 600 CENTRAL AVE.

Midwestern fan-favorite festival, Stews & Brews, returns to Downtown Highland Park for a fourth year on October 11 at Port Clinton Square (600 Central Ave.). Cool weather means hearty comfort foods and hot beverages; Stews & Brews is the perfect event to warm your body and soul! Wrap up the City’s 2025 event season with savory stews and delicious brews, live music, and a cozy atmosphere.

Stews & Brews is not your ordinary chili cook-off or craft beer fest. This free, all-ages event offers attendees an array of cold weather comfort foods like chili, pozole, lamb stew, beef stroganoff, Hungarian goulash, potpies, and a variety of soups. Attendees can pair their dish of choice with dozens of unique brews including craft beers, spiced wine, hot toddies, mulled ciders and more!



View Event →
Ravinia Farmers Market
Oct
8

Ravinia Farmers Market

Ravinia Farmers Market

Wednesdays, June 4 - October 29 | 7 AM - 1 PM
Jens Jensen Park | 540 Roger Williams Ave.


Head to the heart of Highland Park’s Ravinia District for your favorite local farmers market! Shop seasonal produce, meet local vendors, and enjoy live performances throughout the morning.

ENTERTAINMENT

  • 9 AM – 10 AM | Jazzman Jeff

  • 10:30 AM – 11:30 AM | Pierce Crask

  • 12 PM – 1 PM | Albie Powers & Friends

View Event →
Ravinia Farmers Market
Oct
1

Ravinia Farmers Market

Ravinia Farmers Market

Wednesdays, June 4 - October 29 | 7 AM - 1 PM
Jens Jensen Park | 540 Roger Williams Ave.


Head to the heart of Highland Park’s Ravinia District for your favorite local farmers market! Shop seasonal produce, meet local vendors, and enjoy live performances throughout the morning.

ENTERTAINMENT

  • 9 AM – 10 AM | Jazzman Jeff

  • 10:30 AM – 11:30 AM | Pierce Crask

  • 12 PM – 1 PM | Albie Powers & Friends

View Event →
Scarecrow Fest & Downtown Concerts at Port Clinton Finale
Sep
26

Scarecrow Fest & Downtown Concerts at Port Clinton Finale

Wrap up the 2025 Downtown Concert series with a fun fall afternoon. Interact with giant, live scarecrow puppets at Port Clinton Square and jam out to awesome tunes:

4 PM - 4:30 PM | Mary Macaroni

4:45 PM - 5:15 PM | Istvan & His Imaginary Band

5:30 PM - 6:30 PM | Ben Tatar & the Tatar Tots

6:30 PM - 8 PM | Saturday June Band

End the afternoon by embarking on a magical Scarecrow Trail! Find over two dozen festive scarecrows across Downtown Highland Park, all decorated by local businesses and sponsored by Mariani Landscape. Be sure to vote for best in show! See the gallery below for last year’s scarecrows.

View Event →
Ravinia Farmers Market
Sep
24

Ravinia Farmers Market

Ravinia Farmers Market

Wednesdays, June 4 - October 29 | 7 AM - 1 PM
Jens Jensen Park | 540 Roger Williams Ave.


Head to the heart of Highland Park’s Ravinia District for your favorite local farmers market! Shop seasonal produce, meet local vendors, and enjoy live performances throughout the morning.

ENTERTAINMENT

  • 9 AM – 10 AM | Jazzman Jeff

  • 10:30 AM – 11:30 AM | Pierce Crask

  • 12 PM – 1 PM | Albie Powers & Friends

View Event →
Downtown Concerts at Port Clinton
Sep
19

Downtown Concerts at Port Clinton

The City of Highland Park’s Downtown Event Series presents:

Downtown Concerts at Port Clinton

September 19 | 6 PM - 8 PM
Port Clinton Square | 600 Central Ave.


What’s better than a summertime Friday evening? A summertime Friday evening with a concert! The City of Highland Park is excited to announce the return of free, City-sponsored Downtown concerts at Port Clinton Square (600 Central Ave.) on select Friday evenings July 11 through September 26. Bring a lawn chair and kickoff your weekend with live music from a diverse range of artists and genres including: folk, reggae, blues, soul, classic rock, Latin, and more.

SEPTEMBER 19 LINEUP
Entertainment
Dave Specter | Chicago Blues

Food & Beverage
Steep Ravine Brewing Company
Fluffy Bunny
Yana’s Speakeasy

View Event →
Food Truck Thursdays
Sep
18

Food Truck Thursdays

Food Truck Thursdays

June 5 - September 18 | 4:30 PM - Dusk
Jens Jensen Park | 540 Roger Williams Ave.


Mark your calendars: Food Truck Thursdays returns to the Ravinia District this summer, June 5 through September 18, at Jens Jensen Park! Savor fresh flavors from a variety of food trucks, including Highland Park vendors Abigail’s American Bistro, Indus Progressive Indian, Michael’s Grill & Salad Bar, Shaevitz Kosher Market & BBQ, and Steep Ravine Brewing Company while enjoying warm summer evenings and dancing to great music every Thursday night, 4:30 PM to dusk in the Ravinia District!

We can’t imagine a better way to spend a summer evening than good friends, good food, and of course, great music.

 

SEPTEMBER 18 LINEUP

  • 5 PM - 7 PM | JP & Jenny And The Flames

 
 

FEATURED TRUCKS

Bumbu Roux, Chessie Struck, Chicago Lunch Box, Chill’s Italian Ice, Cousins Maine Lobster, Culinary Gangster Glenview, Frankie Da Pizza Dude, Goodstuff Eats, Hawaiian Food Truck, Hello Boba Truck, Kona Ice, La Cocinita, Limoni Belli, Little Louies, Mamalicous Cooking, Maiztify, My Funnel Truck, Nettle Creek Foods, Royal Ice Cream, San Judas Food Truck, Sausage Fest Truck, Taco Motora, Taste Greek Good, Tievoli Pizza Bar, and Yum Dum Truck

Food Truck Thursdays are presented by the City of Highland Park and the Ravinia District Special Service Area 17 property owners, and are managed by Bensidoun USA. The music for Food Truck Thursdays is coordinated by Life Rhythms, Inc., and is co-sponsored by the Highland Park Community Foundation. Additional event sponsors include Wayfarer Theaters. For more information on how to be a part of the 2025 event season as a participating or sponsoring business, please contact the Ravinia District’s event management team, Ripple Public Relations, info@ripplepublicrelations.com, or call 847.432.6000.

View Event →
Ravinia Farmers Market
Sep
17

Ravinia Farmers Market

Ravinia Farmers Market

Wednesdays, June 4 - October 29 | 7 AM - 1 PM
Jens Jensen Park | 540 Roger Williams Ave.


Head to the heart of Highland Park’s Ravinia District for your favorite local farmers market! Shop seasonal produce, meet local vendors, and enjoy live performances throughout the morning.

ENTERTAINMENT

  • 9 AM – 10 AM | Jazzman Jeff

  • 10:30 AM – 11:30 AM | Pierce Crask

  • 12 PM – 1 PM | Albie Powers & Friends

View Event →
Downtown Concerts at Port Clinton
Sep
12

Downtown Concerts at Port Clinton

The City of Highland Park’s Downtown Event Series presents:

Downtown Concerts at Port Clinton

September 12 | 6 PM - 8 PM
Port Clinton Square | 600 Central Ave.


What’s better than a summertime Friday evening? A summertime Friday evening with a concert! The City of Highland Park is excited to announce the return of free, City-sponsored Downtown concerts at Port Clinton Square (600 Central Ave.) on select Friday evenings July 11 through September 26. Bring a lawn chair and kickoff your weekend with live music from a diverse range of artists and genres including: folk, reggae, blues, soul, classic rock, Latin, and more.

SEPTEMBER 12 LINEUP
Entertainment
Don Stiernberg Quartet, Feat. Petra van Nuis | Jazz

Food & Beverage
Steep Ravine Brewing Company
Fluffy Bunny
Awesome Mini Donuts

View Event →
Food Truck Thursdays
Sep
11

Food Truck Thursdays

Food Truck Thursdays

June 5 - September 18 | 4:30 PM - Dusk
Jens Jensen Park | 540 Roger Williams Ave.


Mark your calendars: Food Truck Thursdays returns to the Ravinia District this summer, June 5 through September 18, at Jens Jensen Park! Savor fresh flavors from a variety of food trucks, including Highland Park vendors Abigail’s American Bistro, Indus Progressive Indian, Michael’s Grill & Salad Bar, Shaevitz Kosher Market & BBQ, and Steep Ravine Brewing Company while enjoying warm summer evenings and dancing to great music every Thursday night, 4:30 PM to dusk in the Ravinia District!

We can’t imagine a better way to spend a summer evening than good friends, good food, and of course, great music.

 

SEPTEMBER 11 LINEUP

  • 5 PM - 7:30 PM | Dr. Mark and The Sutures

 
 

FEATURED TRUCKS

Bumbu Roux, Chessie Struck, Chicago Lunch Box, Chill’s Italian Ice, Cousins Maine Lobster, Culinary Gangster Glenview, Frankie Da Pizza Dude, Goodstuff Eats, Hawaiian Food Truck, Hello Boba Truck, Kona Ice, La Cocinita, Limoni Belli, Little Louies, Mamalicous Cooking, Maiztify, My Funnel Truck, Nettle Creek Foods, Royal Ice Cream, San Judas Food Truck, Sausage Fest Truck, Taco Motora, Taste Greek Good, Tievoli Pizza Bar, and Yum Dum Truck

Food Truck Thursdays are presented by the City of Highland Park and the Ravinia District Special Service Area 17 property owners, and are managed by Bensidoun USA. The music for Food Truck Thursdays is coordinated by Life Rhythms, Inc., and is co-sponsored by the Highland Park Community Foundation. Additional event sponsors include Wayfarer Theaters. For more information on how to be a part of the 2025 event season as a participating or sponsoring business, please contact the Ravinia District’s event management team, Ripple Public Relations, info@ripplepublicrelations.com, or call 847.432.6000.

View Event →
Ravinia Farmers Market
Sep
10

Ravinia Farmers Market

Ravinia Farmers Market

Wednesdays, June 4 - October 29 | 7 AM - 1 PM
Jens Jensen Park | 540 Roger Williams Ave.


Head to the heart of Highland Park’s Ravinia District for your favorite local farmers market! Shop seasonal produce, meet local vendors, and enjoy live performances throughout the morning.

ENTERTAINMENT

  • 9 AM – 10 AM | Jazzman Jeff

  • 10:30 AM – 11:30 AM | Pierce Crask

  • 12 PM – 1 PM | Albie Powers & Friends

View Event →
Vintage Car Show
Sep
6

Vintage Car Show

  • 525 Central Avenue Highland Park, IL, 60035 United States (map)
  • Google Calendar ICS

Vintage Car Show

SEPT. 6 | 12 PM - 4 PM
525 CENTRAL AVE.

Step back in time and experience the elegance, craftsmanship, and the nostalgia of a bygone era. Relive the golden age of automobiles at the Vintage Car Show on Saturday, September 6. Head to the St. John’s lot (525 Central Ave.) and peruse a fabulous array of vintage vehicles, while enjoying a live radio broadcast, kid-friendly activities, delicious food, and ice cold beverages.

Whether you’re a seasoned collector or simply curious, you will definitely enjoy this journey through automotive excellence. Expect to see a diverse line up of cars featuring vintage and antique models, unique classics, muscle cars, hot rods, and pop culture icons.



View Event →
Downtown Concerts at Port Clinton
Sep
5

Downtown Concerts at Port Clinton

The City of Highland Park’s Downtown Event Series presents:

Downtown Concerts at Port Clinton

September 5 | 6 PM - 8 PM
Port Clinton Square | 600 Central Ave.


What’s better than a summertime Friday evening? A summertime Friday evening with a concert! The City of Highland Park is excited to announce the return of free, City-sponsored Downtown concerts at Port Clinton Square (600 Central Ave.) on select Friday evenings July 11 through September 26. Bring a lawn chair and kickoff your weekend with live music from a diverse range of artists and genres including: folk, reggae, blues, soul, classic rock, Latin, and more.

SEPTEMBER 5 LINEUP
Entertainment
Radio Free Honduras | Latin Rock

Food & Beverage
Steep Ravine Brewing Company
Fluffy Bunny
Yellow Duck Truck

View Event →
Food Truck Thursdays
Sep
4

Food Truck Thursdays

SEPTEMBER 4 LINEUP

  • 5 PM - 7 PM | Railheart | Ultimate Grateful Dead Cover Band

Food Truck Thursdays

June 5 - September 18 | 4:30 PM - Dusk
Jens Jensen Park | 540 Roger Williams Ave.


Mark your calendars: Food Truck Thursdays returns to the Ravinia District this summer, June 5 through September 18, at Jens Jensen Park! Savor fresh flavors from a variety of food trucks, including Highland Park vendors Abigail’s American Bistro, Indus Progressive Indian, Michael’s Grill & Salad Bar, Shaevitz Kosher Market & BBQ, and Steep Ravine Brewing Company while enjoying warm summer evenings and dancing to great music every Thursday night, 4:30 PM to dusk in the Ravinia District!

We can’t imagine a better way to spend a summer evening than good friends, good food, and of course, great music.

 
 

FEATURED TRUCKS

Bumbu Roux, Chessie Struck, Chicago Lunch Box, Chill’s Italian Ice, Cousins Maine Lobster, Culinary Gangster Glenview, Frankie Da Pizza Dude, Goodstuff Eats, Hawaiian Food Truck, Hello Boba Truck, Kona Ice, La Cocinita, Limoni Belli, Little Louies, Mamalicous Cooking, Maiztify, My Funnel Truck, Nettle Creek Foods, Royal Ice Cream, San Judas Food Truck, Sausage Fest Truck, Taco Motora, Taste Greek Good, Tievoli Pizza Bar, and Yum Dum Truck

 

Food Truck Thursdays are presented by the City of Highland Park and the Ravinia District Special Service Area 17 property owners, and are managed by Bensidoun USA. The music for Food Truck Thursdays is coordinated by Life Rhythms, Inc., and is co-sponsored by the Highland Park Community Foundation. Additional event sponsors include Wayfarer Theaters. For more information on how to be a part of the 2025 event season as a participating or sponsoring business, please contact the Ravinia District’s event management team, Ripple Public Relations, info@ripplepublicrelations.com, or call 847.432.6000.

View Event →
Ravinia Farmers Market
Sep
3

Ravinia Farmers Market

Ravinia Farmers Market

Wednesdays, June 4 - October 29 | 7 AM - 1 PM
Jens Jensen Park | 540 Roger Williams Ave.


Head to the heart of Highland Park’s Ravinia District for your favorite local farmers market! Shop seasonal produce, meet local vendors, and enjoy live performances throughout the morning.

ENTERTAINMENT

  • 9 AM – 10 AM | Jazzman Jeff

  • 10:30 AM – 11:30 AM | Pierce Crask

  • 12 PM – 1 PM | Albie Powers & Friends

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Downtown Concerts at Port Clinton
Aug
29

Downtown Concerts at Port Clinton

The City of Highland Park’s Downtown Event Series presents:

Downtown Concerts at Port Clinton

August 29 | 6 PM - 8 PM
Port Clinton Square | 600 Central Ave.


What’s better than a summertime Friday evening? A summertime Friday evening with a concert! The City of Highland Park is excited to announce the return of free, City-sponsored Downtown concerts at Port Clinton Square (600 Central Ave.) on select Friday evenings July 11 through September 26. Bring a lawn chair and kickoff your weekend with live music from a diverse range of artists and genres including: folk, reggae, blues, soul, classic rock, Latin, and more.

AUGUST 29 LINEUP
Entertainment
Guitarra Azul | Flamenco

Food & Beverage
Steep Ravine Brewing Company
Fluffy Bunny
Awesome Mini Donuts

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Food Truck Thursdays
Aug
28

Food Truck Thursdays

AUGUST 28 LINEUP

Food Truck Thursdays

June 5 - September 18 | 4:30 PM - Dusk
Jens Jensen Park | 540 Roger Williams Ave.


Mark your calendars: Food Truck Thursdays returns to the Ravinia District this summer, June 5 through September 18, at Jens Jensen Park! Savor fresh flavors from a variety of food trucks, including Highland Park vendors Abigail’s American Bistro, Indus Progressive Indian, Michael’s Grill & Salad Bar, Shaevitz Kosher Market & BBQ, and Steep Ravine Brewing Company while enjoying warm summer evenings and dancing to great music every Thursday night, 4:30 PM to dusk in the Ravinia District!

We can’t imagine a better way to spend a summer evening than good friends, good food, and of course, great music.

 
 

FEATURED TRUCKS

Bumbu Roux, Chessie Struck, Chicago Lunch Box, Chill’s Italian Ice, Cousins Maine Lobster, Culinary Gangster Glenview, Frankie Da Pizza Dude, Goodstuff Eats, Hawaiian Food Truck, Hello Boba Truck, Kona Ice, La Cocinita, Limoni Belli, Little Louies, Mamalicous Cooking, Maiztify, My Funnel Truck, Nettle Creek Foods, Royal Ice Cream, San Judas Food Truck, Sausage Fest Truck, Taco Motora, Taste Greek Good, Tievoli Pizza Bar, and Yum Dum Truck

 

Food Truck Thursdays are presented by the City of Highland Park and the Ravinia District Special Service Area 17 property owners, and are managed by Bensidoun USA. The music for Food Truck Thursdays is coordinated by Life Rhythms, Inc., and is co-sponsored by the Highland Park Community Foundation. Additional event sponsors include Wayfarer Theaters. For more information on how to be a part of the 2025 event season as a participating or sponsoring business, please contact the Ravinia District’s event management team, Ripple Public Relations, info@ripplepublicrelations.com, or call 847.432.6000.

View Event →
Ravinia Farmers Market
Aug
27

Ravinia Farmers Market

Ravinia Farmers Market

Wednesdays, June 4 - October 29 | 7 AM - 1 PM
Jens Jensen Park | 540 Roger Williams Ave.


Head to the heart of Highland Park’s Ravinia District for your favorite local farmers market! Shop seasonal produce, meet local vendors, and enjoy live performances throughout the morning.

ENTERTAINMENT

  • 9 AM – 10 AM | Jazzman Jeff

  • 10:30 AM – 11:30 AM | Pierce Crask

  • 12 PM – 1 PM | Albie Powers & Friends

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Port Clinton Art Festival
Aug
23
to Aug 24

Port Clinton Art Festival

Amdur Productions presents

Port Clinton Art Festival

August 23 & 24 | 10 AM - 5 PM
Downtown Highland Park


See paintings, sculpture, mixed media work and more. Get your steps in while browsing thousands of art pieces from over 200 of the best artists in the country. Have kids? Get creative at the Kids Art Zone with art projects, face painting, giant bubbles, painting classes and more. Take a break with a cold beverage, specialty coffee, tasty treats and live music. Look for Kid Friendly Art Tent & Live Art Demo stations and interact with our artists! 

Celebrate 42 years of art at Port Clinton Art Festival in Highland Park

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Food Truck Thursdays
Aug
21

Food Truck Thursdays

AUGUST 21 LINEUP

Food Truck Thursdays

June 5 - September 18 | 4:30 PM - Dusk
Jens Jensen Park | 540 Roger Williams Ave.


Mark your calendars: Food Truck Thursdays returns to the Ravinia District this summer, June 5 through September 18, at Jens Jensen Park! Savor fresh flavors from a variety of food trucks, including Highland Park vendors Abigail’s American Bistro, Indus Progressive Indian, Michael’s Grill & Salad Bar, Shaevitz Kosher Market & BBQ, and Steep Ravine Brewing Company while enjoying warm summer evenings and dancing to great music every Thursday night, 4:30 PM to dusk in the Ravinia District!

We can’t imagine a better way to spend a summer evening than good friends, good food, and of course, great music.

 
 

FEATURED TRUCKS

Bumbu Roux, Chessie Struck, Chicago Lunch Box, Chill’s Italian Ice, Cousins Maine Lobster, Culinary Gangster Glenview, Frankie Da Pizza Dude, Goodstuff Eats, Hawaiian Food Truck, Hello Boba Truck, Kona Ice, La Cocinita, Limoni Belli, Little Louies, Mamalicous Cooking, Maiztify, My Funnel Truck, Nettle Creek Foods, Royal Ice Cream, San Judas Food Truck, Sausage Fest Truck, Taco Motora, Taste Greek Good, Tievoli Pizza Bar, and Yum Dum Truck

 

Food Truck Thursdays are presented by the City of Highland Park and the Ravinia District Special Service Area 17 property owners, and are managed by Bensidoun USA. The music for Food Truck Thursdays is coordinated by Life Rhythms, Inc., and is co-sponsored by the Highland Park Community Foundation. Additional event sponsors include Wayfarer Theaters. For more information on how to be a part of the 2025 event season as a participating or sponsoring business, please contact the Ravinia District’s event management team, Ripple Public Relations, info@ripplepublicrelations.com, or call 847.432.6000.

View Event →
Downtown Concerts at Port Clinton
Aug
15

Downtown Concerts at Port Clinton

The City of Highland Park’s Downtown Event Series presents:

Downtown Concerts at Port Clinton

August 15 | 6 PM - 8 PM
Port Clinton Square | 600 Central Ave.


What’s better than a summertime Friday evening? A summertime Friday evening with a concert! The City of Highland Park is excited to announce the return of free, City-sponsored Downtown concerts at Port Clinton Square (600 Central Ave.) on select Friday evenings July 11 through September 26. Bring a lawn chair and kickoff your weekend with live music from a diverse range of artists and genres including: folk, reggae, blues, soul, classic rock, Latin, and more.

AUGUST 15 LINEUP
Entertainment
Guy King | Vocal Jazz Classics

Food & Beverage
Steep Ravine Brewing Company
Fluffy Bunny
Yellow Duck Truck

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Food Truck Thursdays - Elton John & Billy Joel Nite
Aug
14

Food Truck Thursdays - Elton John & Billy Joel Nite

AUGUST 14 LINEUP

  • 4:30 PM - Dusk | Sing along to all the hits from Elton John and Billy Joel with tribute artist and impersonator, Simply Elton
    Sponsored by Banner Kitchen & Bath

Food Truck Thursdays - Elton John & Billy Joel Nite

August 14 | 4:30 PM - Dusk
Jens Jensen Park | 540 Roger Williams Ave.


Mark your calendars: Food Truck Thursdays returns to the Ravinia District this summer, June 5 through September 18, at Jens Jensen Park! Savor fresh flavors from a variety of food trucks, including Highland Park vendors Abigail’s American Bistro, Indus Progressive Indian, Michael’s Grill & Salad Bar, Shaevitz Kosher Market & BBQ, and Steep Ravine Brewing Company while enjoying warm summer evenings and dancing to great music every Thursday night, 4:30 PM to dusk in the Ravinia District!

We can’t imagine a better way to spend a summer evening than good friends, good food, and of course, great music.

 
 

FEATURED TRUCKS

Bumbu Roux, Chessie Struck, Chicago Lunch Box, Chill’s Italian Ice, Cousins Maine Lobster, Culinary Gangster Glenview, Frankie Da Pizza Dude, Goodstuff Eats, Hawaiian Food Truck, Hello Boba Truck, Kona Ice, La Cocinita, Limoni Belli, Little Louies, Mamalicous Cooking, Maiztify, My Funnel Truck, Nettle Creek Foods, Royal Ice Cream, San Judas Food Truck, Sausage Fest Truck, Taco Motora, Taste Greek Good, Tievoli Pizza Bar, and Yum Dum Truck

 

Food Truck Thursdays are presented by the City of Highland Park and the Ravinia District Special Service Area 17 property owners, and are managed by Bensidoun USA. The music for Food Truck Thursdays is coordinated by Life Rhythms, Inc., and is co-sponsored by the Highland Park Community Foundation. Additional event sponsors include Wayfarer Theaters. For more information on how to be a part of the 2025 event season as a participating or sponsoring business, please contact the Ravinia District’s event management team, Ripple Public Relations, info@ripplepublicrelations.com, or call 847.432.6000.

View Event →
Ravinia Farmers Market
Aug
13

Ravinia Farmers Market

Ravinia Farmers Market

Wednesdays, June 4 - October 29 | 7 AM - 1 PM
Jens Jensen Park | 540 Roger Williams Ave.


Head to the heart of Highland Park’s Ravinia District for your favorite local farmers market! Shop seasonal produce, meet local vendors, and enjoy live performances throughout the morning.

ENTERTAINMENT

  • 9 AM – 10 AM | Jazzman Jeff

  • 10:30 AM – 11:30 AM | Pierce Crask

  • 12 PM – 1 PM | Albie Powers & Friends

View Event →
Downtown Concerts at Port Clinton
Aug
8

Downtown Concerts at Port Clinton

The City of Highland Park’s Downtown Event Series presents:

Downtown Concerts at Port Clinton

August 8 | 6 PM - 8 PM
Port Clinton Square | 600 Central Ave.


What’s better than a summertime Friday evening? A summertime Friday evening with a concert! The City of Highland Park is excited to announce the return of free, City-sponsored Downtown concerts at Port Clinton Square (600 Central Ave.) on select Friday evenings July 11 through September 26. Bring a lawn chair and kickoff your weekend with live music from a diverse range of artists and genres including: folk, reggae, blues, soul, classic rock, Latin, and more.

AUGUST 8 LINEUP
Entertainment
Michelle Hallman Band | Classic Rock & Pop

View Event →