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”
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.

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Downtown Concert at Port Clinton: Treasures of Thailand
Jul
31

Downtown Concert at Port Clinton: Treasures of Thailand

Get ready for a Taste of Thailand with cuisine from Ruby of Siam and perfectly paired wine selections from Lynfred Winery. In addition to sidewalk chalk, bubbles, and bean bag tic tac toe for the kids, entertainment will include music from The Muzik Engine, Thai dancers, and trivia from Wayfarer Theaters & J. Blanton Plumbing.

Downtown Concerts at Port Clinton: Treasures of Thailand

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


Dine & dance your way across the globe this summer in the heart of Highland Park. No passport necessary.

The City of Highland Park's FREE Friday evening concert series returns in 2026 with a special, global twist. Grab your friends, neighbors, and family and head to Port Clinton Square. Over the course of 10 Friday evenings this summer, enjoy world cuisine from HP restaurants with accompanying music and cultural performances.

From Thailand to France to Mexico, Ukraine, Italy, America, India, and beyond, you're invited to experience the flavors that make Highland Park's culinary scene one of the most diverse on Chicago's North Shore.

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.

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Downtown Concert at Port Clinton: American Melting Pot
Aug
7

Downtown Concert at Port Clinton: American Melting Pot

Downtown Concerts at Port Clinton: American Melting Pot

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


Celebrate our great American melting pot with a variety of fusion menu items inspired from around the world from BWB Shakes. Steep Ravine Brewing Company will offer a selection of craft beers.  Enjoy  classic American hits and covers spanning a vast number of genres from Uptown Shakedown.

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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.

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Downtown Concert at Port Clinton: Bon AppétEAT
Aug
14

Downtown Concert at Port Clinton: Bon AppétEAT

Downtown Concerts at Port Clinton: Bon AppétEAT

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


This week will make you think that you’re enjoying a warm summer evening in Montmartre. Enjoy authentic French flavors from That Little French Guy and curated wines from Lynfred Winery. Jazz ensemble Lush Life will provide the perfect Parisian ambiance.

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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.

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Downtown Concert at Port Clinton: Bollywood Beats & Eats
Aug
21

Downtown Concert at Port Clinton: Bollywood Beats & Eats

Downtown Concerts at Port Clinton: Bollywood Beats & Eats

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


Eat to the Bollywood Beat with elevated Indian cuisine from the award-winning Indus Progressive Indian. Bollywood dancers and music from Manmeet Kaur will be the evening’s entertainment.

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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!

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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.

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Downtown Concert at Port Clinton: Nashville Nosh
Sep
4

Downtown Concert at Port Clinton: Nashville Nosh

Downtown Concerts at Port Clinton: Nashville Nosh

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


Nothing makes you feel like family quite like Southern hospitality! Enjoy a family-friendly Nashville-inspired evening with The Barn Steakhouse, County Line String Band, Line Dancing with Heather, along with a Dolly Parton tribute artist.

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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: Notte Italiana
Sep
11

Downtown Concert at Port Clinton: Notte Italiana

Downtown Concerts at Port Clinton: Notte Italiana

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


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One of Highland Park’s newest restaurants, Nico Trattoria & Pizzeria will share your favorite Italian cuisine and cocktails while Steep Ravine Brewing Company serves craft beer. Rat Pack-inspired entertainment from the Diva Montell & Jeorge Holmes Duo  will provide the perfect romantic atmosphere for the evening.

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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: Sabor de Libertad
Sep
18

Downtown Concert at Port Clinton: Sabor de Libertad

Downtown Concerts at Port Clinton: Sabor de Libertad

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


Tamales is turning up the heat in all the best ways with their beloved Mexican cuisine. Grab a drink from Lynfred Winery to toast Mexican Independence Day while salsa dancers groove to the tunes of the Cecy Santana Trio and Orquesta Alta Vida. This is one fiesta you won’t want to miss.

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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.


Commemorate fall with scarecrows, pumpkins, great food, live music, and family fun! The Downtown Concerts Season Finale features a line-up of family-friendly music and activities, seasonal decor, and a Scarecrow Trail through town to see over two dozen festive scarecrows, each uniquely decorated by local businesses, to cast a vote for “Best in Show.” Close out this year’s season of Friday night concerts with world cuisine from Las Torres Mexican Restaurant, Michael’s Grill & Salad Bar, and Indus Progressive Indian. Take part in facepainting, airbrush tattoos, and pumpkin crafts, interact with larger-than-life scarecrow puppets, and jam out to Miss Jamie’s Farm, Istvan & His Imaginary Band, Ben Tatar & the Tatar Tots, and Taylor & Mane.

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Oktoberfest
Sep
26

Oktoberfest

Oktoberfest

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


More info coming soon!

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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 →

Downtown Concert at Port Clinton: Slavic Savor
Jul
17

Downtown Concert at Port Clinton: Slavic Savor

Downtown Concerts at Port Clinton: Slavic Savor

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


Dine & dance your way across the globe this summer in the heart of Highland Park. No passport necessary.

The City of Highland Park's FREE Friday evening concert series returns in 2026 with a special, global twist. Grab your friends, neighbors, and family and head to Port Clinton Square. Over the course of 10 Friday evenings this summer, enjoy world cuisine from HP restaurants with accompanying music and cultural performances.

From Thailand to France to Mexico, Ukraine, Italy, America, India, and beyond, you're invited to experience the flavors that make Highland Park's culinary scene one of the most diverse on Chicago's North Shore.

JUL. 17 | SLAVIC SAVOR

We're headed to Eastern Europe this week with SLAVIC SAVOR. Cafe Dacha will be serving up all your Eastern European favorites and Steep Ravine Brewing Company will offer a selection of craft beers for those 21+. In addition to sidewalk chalk, bubbles, and bean bag tic tac toe for the kids, entertainment will include music from Paul Strolia and Volodymyr Okilko, Ukrainian dancers, and trivia from Wayfarer Theaters & J. Blanton Plumbing.

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 →
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 →
Downtown Concert at Port Clinton: Kosher & Klezmer
Jul
10

Downtown Concert at Port Clinton: Kosher & Klezmer

JULY 10 | KOSHER & KLEZMER

Kick off the series by exploring the Jewish diaspora with KOSHER & KLEZMER. Mizrahi Grill will be serving up kosher cuisine while the Maxwell Street Klezmer Band entertains. Steep Ravine Brewing Company will also be onsite offering libations for those 21+. PLUS, flex your knowledge with trivia during the intermission with Wayfarer Theaters. Kids and adults alike can also enjoy sidewalk chalk, bubbles, and bean bag tic tac toe throughout the evening.

Downtown Concerts at Port Clinton: Kosher & Klezmer

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


Dine & dance your way across the globe this summer in the heart of Highland Park. No passport necessary.

The City of Highland Park's FREE Friday evening concert series returns in 2026 with a special, global twist. Grab your friends, neighbors, and family and head to Port Clinton Square. Over the course of 10 Friday evenings this summer, enjoy world cuisine from HP restaurants with accompanying music and cultural performances.

From Thailand to France to Mexico, Ukraine, Italy, America, India, and beyond, you're invited to experience the flavors that make Highland Park's culinary scene one of the most diverse on Chicago's North Shore.

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.

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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.

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Independence Fest
Jul
3

Independence Fest

The Park District of Highland Park presents

Canceled: Independence Fest

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


Update, July 3: For the safety of our community, performers, vendors, and staff, the City of Highland Park and the Park District of Highland Park, in consultation with the fireworks contractor, have made the difficult decision to cancel Independence Fest and to reschedule the fireworks display to a later date. At this time, no changes are anticipated for the Independence Day parade, scheduled for 10:30 AM and the Star-Spangled Pool Party, scheduled for 11 AM, on Saturday, July 4. 

If you pre-purchased an Independence Fest wristband and would like a refund, please reach out to the Park District's customer service office at registrations@pdhp.org. If you choose not to request a refund, your wristband purchase will be donated to the Parks Foundation of Highland Park Scholarship Fund.

The City will announce the rescheduled fireworks display once a new date has been confirmed. 

We apologize for the inconvenience, and we wish you and your family a safe and happy holiday weekend. We look forward to celebrating with you at the Independence Day Parade and the Star-Spangled Pool Party!

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.

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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 →
20th Anniversary Bitter Jester Music Festival: Grand Finale
Jun
27

20th Anniversary Bitter Jester Music Festival: Grand Finale

20th Anniversary

Bitter Jester Music Festival - 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.


Grand Finale Lineup

IN COMPETITION:
WINNERS: Exit 122, Taranis, Threegon, Tripsitter‍‍
WILDCARDS: Mistrophia, Cabin Fever, Hammerhead, Belle Vista

FEATURED SHOWCASE:
Billy Schaumann, Izzy Savides, Mystik, The Strolls

GUEST ARTIST:
Claire McKenna

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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 →
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.

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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.

FREE


The Taste of Highland Park is downtown Highland Park’s premiere, all-ages dining and music festival.

The City of Highland Park is bringing the ultimate outdoor entertainment and dining experience to Downtown Highland Park with the Taste of Highland Park June 19 from 5 PM - 10 PM & June 20 from 3 PM - 10 PM. Located along Central Avenue, between Second St. and St. Johns Ave., and in Port Clinton Square (600 Central Ave.), sample over a dozen local food and beverage vendors and get a taste of what sets Highland Park’s restaurant scene apart on Chicago’s North Shore.

Get ready for more food, more music, and even more fun for 2026!

New for 2026: Enhance your experience with air conditioned seating & dining areas, as well as an all-new photography exhibit showcasing the winners of the Capture the Heart of Highland Park photography contest. Plus, families will enjoy special children-focused programming from 3 PM - 5 PM on Saturday. Lastly, Highland Park’s very own Bitter Jester Music Festival, celebrating 20 years in HP, will program 5:30 PM - 6:30 PM on Saturday.

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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 →
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 →
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.

View Event →
Arts on Sheridan
Jun
13
to Jun 14

Arts on Sheridan

Amdur Productions presents

Arts on Sheridan

JUN. 13 & JUN. 14 | 10 AM - 5 PM | FREE
Downtown Highland Park


This June 13 and 14, join Amdur Productions at the second annual Arts on Sheridan! Stroll through the art and design district in east Highland Park and explore a curated selection of art from talented artists across all mediums. Don’t miss out on this exciting art festival! With a Kids Art Zone, live music, food and beverage, and live art demonstrations, there is something for the whole family all weekend long!

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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.

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 →
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 →
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.

View Event →
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.

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.

View Event →
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 →
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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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.

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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!



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