Wayfarer Theaters presents

Director Spotlight: Jessica Redish

MAY 3 | 4 PM - 5:15 PM | $15 general admission / $12 seniors & children
Wayfarer Theaters - 1850 Second St.

Wayfarer Theaters presents a special spotlight screening of short films by director, writer, choreographer, and Highland Park Native Jessica Redish on May 3. Enjoy a curated showcase of Redish’s acclaimed comedic and musical short films followed by exclusive previews of her newest work and upcoming projects. Known for blending humor, psychological insight, and stylized storytelling, Redish’s films often center on women navigating heightened, sometimes absurd circumstances. The retrospective will feature The Last Croissant, AIRWAY, Instacart, Getting Out, Tailored to You, Cat, Brighter Days, and Exit, Pursued by a Bear.

2nd Annual Downtown Highland Park

Women-Owned Business Whistle Stop Trolley Tour

MAY 7 | 4 PM - 9 PM | $20

All aboard! Get ready for the second annual Downtown Highland Park Women-Owned Business Whistle Stop Trolley Tour! Visit over 35 women-owned businesses throughout Downtown Highland Park on May 7 from 4 PM - 7 PM Enjoy an after party and prize giveaway from 7 PM - 9 PM at Dayhouse Coworking (2057 Green Bay Rd., Ste. A) after the tour.

This event is not produced by the City of Highland Park. For more information about this event, please contact Ripple Public Relations.

Compost Giveback & Secure Document Shredding

MAY 9 | Compost 9 AM - 10 AM / Shredding 10 AM - 1 PM | FREE
Hidden Creek AquaPark Parking Lot - 1220 Fredrickson Pl.

Celebrate International Compost Awareness week with GoGreen Highland Park, in partnership with Swalco, the Park District of Highland Park, and the City of Highland Park, on May 9 at Hidden Creek AquaPark. A truckload of locally-made, nutrient-rich compost will be waiting for Highland Park residents from 9 AM - 10 AM. Spread the love in your vegetable gardens, flowerbeds, planters and lawns with this naturally produced soil amendment. New for 2026, residents will be able to securely dispose of documents with confidential document shredding from 10 AM - 1 PM (limit of 6 banker boxes per household).

Memorial Day Observance

MAY 31 | 11 AM
Location TBA

Save the date for the City of Highland Park’s 2026 Memorial Day Observance on Monday, May 31 2026. Location and program details TBA.

North Shore Classic Half Marathon 5K & Kids Dash

MAY 31 | 7 AM 5K Start / 7:30 AM Half Marathon Start | Register by MAY 15
Starting Line | Intersection of St. Johns Ave. & Central Ave.

The annual North Shore Classic will take place on Sunday, May 31, 2026. Celebrate community and sportsmanship as you run through the picturesque streets of Highland Park.

Whether you’re charging the half marathon or hustling the 5K, the excitement doesn’t end at the finish line. Join thousands of fellow runners for a post-race picnic packed with live music, delicious grilled bites, refreshing drinks, and plenty of fun to cap off an unforgettable day.

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.

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.

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.

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.

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.

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.

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.

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.

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.

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.

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.

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.

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.

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.

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.

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.

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.

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.

The City of Highland Park & the Park District of Highland Park present

Independence Day Fireworks Display

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

Community members will enjoy a spectacular fireworks display set to a patriotic soundtrack in celebration of America250.

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.

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.

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.

Downtown Concerts at Port Clinton: Kick Off

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

More info coming soon!

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.

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.

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.

Downtown Concerts at Port Clinton

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

More info coming soon!

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.

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.

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.

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

JUL. 24 | 8 PM
Ravinia Festival | Hunter Pavilion

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. 

America250 at Ravinia Festival - Chanticleer: Our American Journey

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

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. 

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.

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.

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.

Downtown Concerts at Port Clinton

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

More info coming soon!

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

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

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. 

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

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

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. 

America250 at Ravinia Festival - This Land: America in Song

AUG. 2 | 5 PM
Ravinia Festival | Hunter Pavilion

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.

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.

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.

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.

Downtown Concerts at Port Clinton

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

More info coming soon!

America250 at Ravinia Festival - This Land: America in Song

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

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.

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.

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.

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.

Downtown Concerts at Port Clinton

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

More info coming soon!

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.

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.

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.

Downtown Concerts at Port Clinton

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

More info coming soon!

Vintage Car Show

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

More info coming soon!

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.

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.

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.

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.

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.

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.

Downtown Concerts at Port Clinton

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

More info coming soon!

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.

Downtown Concerts at Port Clinton

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

More info coming soon!

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.

Downtown Concerts at Port Clinton

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

More info coming soon!

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.

Downtown Concerts at Port Clinton: Finale & Scarecrow Trail

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

More info coming soon!

Oktoberfest

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

More info coming soon!

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.

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.

Stews & Brews

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

More info coming soon!

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.

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.

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.

Veteran’s Day Observance

NOV. 11 | 11 AM

The City of Highland Park will hosts its annual Veterans Day Observance on Wednesday, November 11, 2026 at 11AM. Details on location and program TBA

Holiday Lighting

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

More info coming soon!