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
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
Food Truck Thursdays
JULY 31 LINEUP
4:30 PM - 5:45 PM | Pierce Crask & Ellis Clark | Delta blues folk
6 PM - 8:30 PM | Basement Band | Local classic rock band covering the Beatles, Elvis, the Eagles, and more
Food Truck Thursdays
June 5 - September 18 | 4:30 PM - Dusk
Jens Jensen Park | 540 Roger Williams Ave.
Mark your calendars: Food Truck Thursdays returns to the Ravinia District this summer, June 5 through September 18, at Jens Jensen Park! Savor fresh flavors from a variety of food trucks, including Highland Park vendors Abigail’s American Bistro, Indus Progressive Indian, Michael’s Grill & Salad Bar, Shaevitz Kosher Market & BBQ, and Steep Ravine Brewing Company while enjoying warm summer evenings and dancing to great music every Thursday night, 4:30 PM to dusk in the Ravinia District!
We can’t imagine a better way to spend a summer evening than good friends, good food, and of course, great music.
FEATURED TRUCKS
Bumbu Roux, Chessie Struck, Chicago Lunch Box, Chill’s Italian Ice, Cousins Maine Lobster, Culinary Gangster Glenview, Frankie Da Pizza Dude, Goodstuff Eats, Hawaiian Food Truck, Hello Boba Truck, Kona Ice, La Cocinita, Limoni Belli, Little Louies, Mamalicous Cooking, Maiztify, My Funnel Truck, Nettle Creek Foods, Royal Ice Cream, San Judas Food Truck, Sausage Fest Truck, Taco Motora, Taste Greek Good, Tievoli Pizza Bar, and Yum Dum Truck
Food Truck Thursdays are presented by the City of Highland Park and the Ravinia District Special Service Area 17 property owners, and are managed by Bensidoun USA. The music for Food Truck Thursdays is coordinated by Life Rhythms, Inc., and is co-sponsored by the Highland Park Community Foundation. Additional event sponsors include Wayfarer Theaters. For more information on how to be a part of the 2025 event season as a participating or sponsoring business, please contact the Ravinia District’s event management team, Ripple Public Relations, info@ripplepublicrelations.com, or call 847.432.6000.
Downtown Concerts at Port Clinton
The City of Highland Park’s Downtown Event Series presents:
Downtown Concerts at Port Clinton
August 1 | 6 PM - 8 PM
Port Clinton Square | 600 Central Ave.
What’s better than a summertime Friday evening? A summertime Friday evening with a concert! The City of Highland Park is excited to announce the return of free, City-sponsored Downtown concerts at Port Clinton Square (600 Central Ave.) on select Friday evenings July 11 through September 26. Bring a lawn chair and kickoff your weekend with live music from a diverse range of artists and genres including: folk, reggae, blues, soul, classic rock, Latin, and more.
AUGUST 1 LINEUP
Entertainment
Kaleidoscope Eyes | Beatles Tribute Band
Food & Beverage
Steep Ravine Brewing Company
Fluffy Bunny
National Night Out
The City of Highland Park Police Department will host the annual National Night Out on August 5, 2025 from 6 PM - 8:30 PM.
NEW THIS YEAR: National Night Out will take place at the Hidden Creek Aquapark (1220 Fredrickson Place). Meet the men & women of the Highland Park Police Department and take part in family-friendly games and activities, giveaways, demonstrations, and more.
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
Food Truck Thursdays
AUGUST 7 LINEUP
4:30 PM - 5:45 PM | James Conway Duo | Irish folk
6 PM - 8:30 PM | Extra Crispy Brass Band | 8-piece New Orleans-inspired brass band
Food Truck Thursdays
June 5 - September 18 | 4:30 PM - Dusk
Jens Jensen Park | 540 Roger Williams Ave.
Mark your calendars: Food Truck Thursdays returns to the Ravinia District this summer, June 5 through September 18, at Jens Jensen Park! Savor fresh flavors from a variety of food trucks, including Highland Park vendors Abigail’s American Bistro, Indus Progressive Indian, Michael’s Grill & Salad Bar, Shaevitz Kosher Market & BBQ, and Steep Ravine Brewing Company while enjoying warm summer evenings and dancing to great music every Thursday night, 4:30 PM to dusk in the Ravinia District!
We can’t imagine a better way to spend a summer evening than good friends, good food, and of course, great music.
FEATURED TRUCKS
Bumbu Roux, Chessie Struck, Chicago Lunch Box, Chill’s Italian Ice, Cousins Maine Lobster, Culinary Gangster Glenview, Frankie Da Pizza Dude, Goodstuff Eats, Hawaiian Food Truck, Hello Boba Truck, Kona Ice, La Cocinita, Limoni Belli, Little Louies, Mamalicous Cooking, Maiztify, My Funnel Truck, Nettle Creek Foods, Royal Ice Cream, San Judas Food Truck, Sausage Fest Truck, Taco Motora, Taste Greek Good, Tievoli Pizza Bar, and Yum Dum Truck
Food Truck Thursdays are presented by the City of Highland Park and the Ravinia District Special Service Area 17 property owners, and are managed by Bensidoun USA. The music for Food Truck Thursdays is coordinated by Life Rhythms, Inc., and is co-sponsored by the Highland Park Community Foundation. Additional event sponsors include Wayfarer Theaters. For more information on how to be a part of the 2025 event season as a participating or sponsoring business, please contact the Ravinia District’s event management team, Ripple Public Relations, info@ripplepublicrelations.com, or call 847.432.6000.
Downtown Concerts at Port Clinton
The City of Highland Park’s Downtown Event Series presents:
Downtown Concerts at Port Clinton
August 8 | 6 PM - 8 PM
Port Clinton Square | 600 Central Ave.
What’s better than a summertime Friday evening? A summertime Friday evening with a concert! The City of Highland Park is excited to announce the return of free, City-sponsored Downtown concerts at Port Clinton Square (600 Central Ave.) on select Friday evenings July 11 through September 26. Bring a lawn chair and kickoff your weekend with live music from a diverse range of artists and genres including: folk, reggae, blues, soul, classic rock, Latin, and more.
AUGUST 8 LINEUP
Entertainment
Michelle Hallman Band | Classic Rock & Pop
Food & Beverage
Indus Progressive Indian
Steep Ravine Brewing Company
Fluffy Bunny
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
Food Truck Thursdays - Elton John & Billy Joel Nite
AUGUST 14 LINEUP
4:30 PM - Dusk | Sing along to all the hits from Elton John and Billy Joel with tribute artist and impersonator, Simply Elton
Sponsored by Banner Kitchen & Bath
Food Truck Thursdays - Elton John & Billy Joel Nite
August 14 | 4:30 PM - Dusk
Jens Jensen Park | 540 Roger Williams Ave.
Mark your calendars: Food Truck Thursdays returns to the Ravinia District this summer, June 5 through September 18, at Jens Jensen Park! Savor fresh flavors from a variety of food trucks, including Highland Park vendors Abigail’s American Bistro, Indus Progressive Indian, Michael’s Grill & Salad Bar, Shaevitz Kosher Market & BBQ, and Steep Ravine Brewing Company while enjoying warm summer evenings and dancing to great music every Thursday night, 4:30 PM to dusk in the Ravinia District!
We can’t imagine a better way to spend a summer evening than good friends, good food, and of course, great music.
FEATURED TRUCKS
Bumbu Roux, Chessie Struck, Chicago Lunch Box, Chill’s Italian Ice, Cousins Maine Lobster, Culinary Gangster Glenview, Frankie Da Pizza Dude, Goodstuff Eats, Hawaiian Food Truck, Hello Boba Truck, Kona Ice, La Cocinita, Limoni Belli, Little Louies, Mamalicous Cooking, Maiztify, My Funnel Truck, Nettle Creek Foods, Royal Ice Cream, San Judas Food Truck, Sausage Fest Truck, Taco Motora, Taste Greek Good, Tievoli Pizza Bar, and Yum Dum Truck
Food Truck Thursdays are presented by the City of Highland Park and the Ravinia District Special Service Area 17 property owners, and are managed by Bensidoun USA. The music for Food Truck Thursdays is coordinated by Life Rhythms, Inc., and is co-sponsored by the Highland Park Community Foundation. Additional event sponsors include Wayfarer Theaters. For more information on how to be a part of the 2025 event season as a participating or sponsoring business, please contact the Ravinia District’s event management team, Ripple Public Relations, info@ripplepublicrelations.com, or call 847.432.6000.
Downtown Concerts at Port Clinton
The City of Highland Park’s Downtown Event Series presents:
Downtown Concerts at Port Clinton
August 15 | 6 PM - 8 PM
Port Clinton Square | 600 Central Ave.
What’s better than a summertime Friday evening? A summertime Friday evening with a concert! The City of Highland Park is excited to announce the return of free, City-sponsored Downtown concerts at Port Clinton Square (600 Central Ave.) on select Friday evenings July 11 through September 26. Bring a lawn chair and kickoff your weekend with live music from a diverse range of artists and genres including: folk, reggae, blues, soul, classic rock, Latin, and more.
AUGUST 15 LINEUP
Entertainment
Guy King | Vocal Jazz Classics
Food & Beverage
Steep Ravine Brewing Company
Fluffy Bunny
Yellow Duck Truck
Taste of Ravinia
Wednesday, August 20 | 7 AM - 1PM
Jens Jensen Park | 450 Roger Williams Ave.
4 PM - 9 PM
Ravinia Festival Grounds | 200 Ravinia Park
Food Truck Thursdays
AUGUST 21 LINEUP
4:30 PM - 5:45 PM | Wincanton | Local jam band duo
6 PM - 8:30 PM | Sara Jean Stevens & the Swamp Angels | Country soul
Food Truck Thursdays
June 5 - September 18 | 4:30 PM - Dusk
Jens Jensen Park | 540 Roger Williams Ave.
Mark your calendars: Food Truck Thursdays returns to the Ravinia District this summer, June 5 through September 18, at Jens Jensen Park! Savor fresh flavors from a variety of food trucks, including Highland Park vendors Abigail’s American Bistro, Indus Progressive Indian, Michael’s Grill & Salad Bar, Shaevitz Kosher Market & BBQ, and Steep Ravine Brewing Company while enjoying warm summer evenings and dancing to great music every Thursday night, 4:30 PM to dusk in the Ravinia District!
We can’t imagine a better way to spend a summer evening than good friends, good food, and of course, great music.
FEATURED TRUCKS
Bumbu Roux, Chessie Struck, Chicago Lunch Box, Chill’s Italian Ice, Cousins Maine Lobster, Culinary Gangster Glenview, Frankie Da Pizza Dude, Goodstuff Eats, Hawaiian Food Truck, Hello Boba Truck, Kona Ice, La Cocinita, Limoni Belli, Little Louies, Mamalicous Cooking, Maiztify, My Funnel Truck, Nettle Creek Foods, Royal Ice Cream, San Judas Food Truck, Sausage Fest Truck, Taco Motora, Taste Greek Good, Tievoli Pizza Bar, and Yum Dum Truck
Food Truck Thursdays are presented by the City of Highland Park and the Ravinia District Special Service Area 17 property owners, and are managed by Bensidoun USA. The music for Food Truck Thursdays is coordinated by Life Rhythms, Inc., and is co-sponsored by the Highland Park Community Foundation. Additional event sponsors include Wayfarer Theaters. For more information on how to be a part of the 2025 event season as a participating or sponsoring business, please contact the Ravinia District’s event management team, Ripple Public Relations, info@ripplepublicrelations.com, or call 847.432.6000.
Port Clinton Art Festival
Amdur Productions presents
Port Clinton Art Festival
August 23 & 24 | 10 AM - 5 PM
Downtown Highland Park
See paintings, sculpture, mixed media work and more. Get your steps in while browsing thousands of art pieces from over 200 of the best artists in the country. Have kids? Get creative at the Kids Art Zone with art projects, face painting, giant bubbles, painting classes and more. Take a break with a cold beverage, specialty coffee, tasty treats and live music. Look for Kid Friendly Art Tent & Live Art Demo stations and interact with our artists!
Celebrate 42 years of art at Port Clinton Art Festival in Highland Park
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
Food Truck Thursdays
AUGUST 28 LINEUP
4:30 PM - 5:45 PM | Noah’s Jam Jam Band Bourée | Children’s entertainer
6 PM - 8:30 PM | K-Nein | 10-piece Americana rock’n’roll band with horns
Food Truck Thursdays
June 5 - September 18 | 4:30 PM - Dusk
Jens Jensen Park | 540 Roger Williams Ave.
Mark your calendars: Food Truck Thursdays returns to the Ravinia District this summer, June 5 through September 18, at Jens Jensen Park! Savor fresh flavors from a variety of food trucks, including Highland Park vendors Abigail’s American Bistro, Indus Progressive Indian, Michael’s Grill & Salad Bar, Shaevitz Kosher Market & BBQ, and Steep Ravine Brewing Company while enjoying warm summer evenings and dancing to great music every Thursday night, 4:30 PM to dusk in the Ravinia District!
We can’t imagine a better way to spend a summer evening than good friends, good food, and of course, great music.
FEATURED TRUCKS
Bumbu Roux, Chessie Struck, Chicago Lunch Box, Chill’s Italian Ice, Cousins Maine Lobster, Culinary Gangster Glenview, Frankie Da Pizza Dude, Goodstuff Eats, Hawaiian Food Truck, Hello Boba Truck, Kona Ice, La Cocinita, Limoni Belli, Little Louies, Mamalicous Cooking, Maiztify, My Funnel Truck, Nettle Creek Foods, Royal Ice Cream, San Judas Food Truck, Sausage Fest Truck, Taco Motora, Taste Greek Good, Tievoli Pizza Bar, and Yum Dum Truck
Food Truck Thursdays are presented by the City of Highland Park and the Ravinia District Special Service Area 17 property owners, and are managed by Bensidoun USA. The music for Food Truck Thursdays is coordinated by Life Rhythms, Inc., and is co-sponsored by the Highland Park Community Foundation. Additional event sponsors include Wayfarer Theaters. For more information on how to be a part of the 2025 event season as a participating or sponsoring business, please contact the Ravinia District’s event management team, Ripple Public Relations, info@ripplepublicrelations.com, or call 847.432.6000.
Downtown Concerts at Port Clinton
The City of Highland Park’s Downtown Event Series presents:
Downtown Concerts at Port Clinton
August 29 | 6 PM - 8 PM
Port Clinton Square | 600 Central Ave.
What’s better than a summertime Friday evening? A summertime Friday evening with a concert! The City of Highland Park is excited to announce the return of free, City-sponsored Downtown concerts at Port Clinton Square (600 Central Ave.) on select Friday evenings July 11 through September 26. Bring a lawn chair and kickoff your weekend with live music from a diverse range of artists and genres including: folk, reggae, blues, soul, classic rock, Latin, and more.
AUGUST 29 LINEUP
Entertainment
Guitarra Azul | Flamenco
Food & Beverage
Steep Ravine Brewing Company
Fluffy Bunny
Awesome Mini Donuts
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
Food Truck Thursdays
SEPTEMBER 4 LINEUP
5 PM - 7 PM | Railheart | Ultimate Grateful Dead Cover Band
Food Truck Thursdays
June 5 - September 18 | 4:30 PM - Dusk
Jens Jensen Park | 540 Roger Williams Ave.
Mark your calendars: Food Truck Thursdays returns to the Ravinia District this summer, June 5 through September 18, at Jens Jensen Park! Savor fresh flavors from a variety of food trucks, including Highland Park vendors Abigail’s American Bistro, Indus Progressive Indian, Michael’s Grill & Salad Bar, Shaevitz Kosher Market & BBQ, and Steep Ravine Brewing Company while enjoying warm summer evenings and dancing to great music every Thursday night, 4:30 PM to dusk in the Ravinia District!
We can’t imagine a better way to spend a summer evening than good friends, good food, and of course, great music.
FEATURED TRUCKS
Bumbu Roux, Chessie Struck, Chicago Lunch Box, Chill’s Italian Ice, Cousins Maine Lobster, Culinary Gangster Glenview, Frankie Da Pizza Dude, Goodstuff Eats, Hawaiian Food Truck, Hello Boba Truck, Kona Ice, La Cocinita, Limoni Belli, Little Louies, Mamalicous Cooking, Maiztify, My Funnel Truck, Nettle Creek Foods, Royal Ice Cream, San Judas Food Truck, Sausage Fest Truck, Taco Motora, Taste Greek Good, Tievoli Pizza Bar, and Yum Dum Truck
Food Truck Thursdays are presented by the City of Highland Park and the Ravinia District Special Service Area 17 property owners, and are managed by Bensidoun USA. The music for Food Truck Thursdays is coordinated by Life Rhythms, Inc., and is co-sponsored by the Highland Park Community Foundation. Additional event sponsors include Wayfarer Theaters. For more information on how to be a part of the 2025 event season as a participating or sponsoring business, please contact the Ravinia District’s event management team, Ripple Public Relations, info@ripplepublicrelations.com, or call 847.432.6000.
Downtown Concerts at Port Clinton
The City of Highland Park’s Downtown Event Series presents:
Downtown Concerts at Port Clinton
September 5 | 6 PM - 8 PM
Port Clinton Square | 600 Central Ave.
What’s better than a summertime Friday evening? A summertime Friday evening with a concert! The City of Highland Park is excited to announce the return of free, City-sponsored Downtown concerts at Port Clinton Square (600 Central Ave.) on select Friday evenings July 11 through September 26. Bring a lawn chair and kickoff your weekend with live music from a diverse range of artists and genres including: folk, reggae, blues, soul, classic rock, Latin, and more.
SEPTEMBER 5 LINEUP
Entertainment
Radio Free Honduras | Latin Rock
Food & Beverage
Steep Ravine Brewing Company
Fluffy Bunny
Yellow Duck Truck
Vintage Car Show
Vintage Car Show
SEPT. 6 | 12 PM - 4 PM
525 CENTRAL AVE.
Step back in time and experience the elegance, craftsmanship, and the nostalgia of a bygone era. Relive the golden age of automobiles at the Vintage Car Show on Saturday, September 6. Head to the St. John’s lot (525 Central Ave.) and peruse a fabulous array of vintage vehicles, while enjoying a live radio broadcast, kid-friendly activities, delicious food, and ice cold beverages.
Whether you’re a seasoned collector or simply curious, you will definitely enjoy this journey through automotive excellence. Expect to see a diverse line up of cars featuring vintage and antique models, unique classics, muscle cars, hot rods, and pop culture icons.
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
Food Truck Thursdays
Food Truck Thursdays
June 5 - September 18 | 4:30 PM - Dusk
Jens Jensen Park | 540 Roger Williams Ave.
Mark your calendars: Food Truck Thursdays returns to the Ravinia District this summer, June 5 through September 18, at Jens Jensen Park! Savor fresh flavors from a variety of food trucks, including Highland Park vendors Abigail’s American Bistro, Indus Progressive Indian, Michael’s Grill & Salad Bar, Shaevitz Kosher Market & BBQ, and Steep Ravine Brewing Company while enjoying warm summer evenings and dancing to great music every Thursday night, 4:30 PM to dusk in the Ravinia District!
We can’t imagine a better way to spend a summer evening than good friends, good food, and of course, great music.
SEPTEMBER 11 LINEUP
5 PM - 7 PM | DJ Spinning Family Friendly Tunes from Steep Ravine Brewing Company
FEATURED TRUCKS
Bumbu Roux, Chessie Struck, Chicago Lunch Box, Chill’s Italian Ice, Cousins Maine Lobster, Culinary Gangster Glenview, Frankie Da Pizza Dude, Goodstuff Eats, Hawaiian Food Truck, Hello Boba Truck, Kona Ice, La Cocinita, Limoni Belli, Little Louies, Mamalicous Cooking, Maiztify, My Funnel Truck, Nettle Creek Foods, Royal Ice Cream, San Judas Food Truck, Sausage Fest Truck, Taco Motora, Taste Greek Good, Tievoli Pizza Bar, and Yum Dum Truck
Food Truck Thursdays are presented by the City of Highland Park and the Ravinia District Special Service Area 17 property owners, and are managed by Bensidoun USA. The music for Food Truck Thursdays is coordinated by Life Rhythms, Inc., and is co-sponsored by the Highland Park Community Foundation. Additional event sponsors include Wayfarer Theaters. For more information on how to be a part of the 2025 event season as a participating or sponsoring business, please contact the Ravinia District’s event management team, Ripple Public Relations, info@ripplepublicrelations.com, or call 847.432.6000.
Downtown Concerts at Port Clinton
The City of Highland Park’s Downtown Event Series presents:
Downtown Concerts at Port Clinton
September 12 | 6 PM - 8 PM
Port Clinton Square | 600 Central Ave.
What’s better than a summertime Friday evening? A summertime Friday evening with a concert! The City of Highland Park is excited to announce the return of free, City-sponsored Downtown concerts at Port Clinton Square (600 Central Ave.) on select Friday evenings July 11 through September 26. Bring a lawn chair and kickoff your weekend with live music from a diverse range of artists and genres including: folk, reggae, blues, soul, classic rock, Latin, and more.
SEPTEMBER 12 LINEUP
Entertainment
Don Stiernberg Quartet, Feat. Petra van Nuis | Jazz
Food & Beverage
Steep Ravine Brewing Company
Fluffy Bunny
Awesome Mini Donuts
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
Food Truck Thursdays
Food Truck Thursdays
June 5 - September 18 | 4:30 PM - Dusk
Jens Jensen Park | 540 Roger Williams Ave.
Mark your calendars: Food Truck Thursdays returns to the Ravinia District this summer, June 5 through September 18, at Jens Jensen Park! Savor fresh flavors from a variety of food trucks, including Highland Park vendors Abigail’s American Bistro, Indus Progressive Indian, Michael’s Grill & Salad Bar, Shaevitz Kosher Market & BBQ, and Steep Ravine Brewing Company while enjoying warm summer evenings and dancing to great music every Thursday night, 4:30 PM to dusk in the Ravinia District!
We can’t imagine a better way to spend a summer evening than good friends, good food, and of course, great music.
SEPTEMBER 18 LINEUP
5 PM - 7 PM | DJ Spinning Family Friendly Tunes from Steep Ravine Brewing Company
FEATURED TRUCKS
Bumbu Roux, Chessie Struck, Chicago Lunch Box, Chill’s Italian Ice, Cousins Maine Lobster, Culinary Gangster Glenview, Frankie Da Pizza Dude, Goodstuff Eats, Hawaiian Food Truck, Hello Boba Truck, Kona Ice, La Cocinita, Limoni Belli, Little Louies, Mamalicous Cooking, Maiztify, My Funnel Truck, Nettle Creek Foods, Royal Ice Cream, San Judas Food Truck, Sausage Fest Truck, Taco Motora, Taste Greek Good, Tievoli Pizza Bar, and Yum Dum Truck
Food Truck Thursdays are presented by the City of Highland Park and the Ravinia District Special Service Area 17 property owners, and are managed by Bensidoun USA. The music for Food Truck Thursdays is coordinated by Life Rhythms, Inc., and is co-sponsored by the Highland Park Community Foundation. Additional event sponsors include Wayfarer Theaters. For more information on how to be a part of the 2025 event season as a participating or sponsoring business, please contact the Ravinia District’s event management team, Ripple Public Relations, info@ripplepublicrelations.com, or call 847.432.6000.
Downtown Concerts at Port Clinton
The City of Highland Park’s Downtown Event Series presents:
Downtown Concerts at Port Clinton
September 19 | 6 PM - 8 PM
Port Clinton Square | 600 Central Ave.
What’s better than a summertime Friday evening? A summertime Friday evening with a concert! The City of Highland Park is excited to announce the return of free, City-sponsored Downtown concerts at Port Clinton Square (600 Central Ave.) on select Friday evenings July 11 through September 26. Bring a lawn chair and kickoff your weekend with live music from a diverse range of artists and genres including: folk, reggae, blues, soul, classic rock, Latin, and more.
SEPTEMBER 19 LINEUP
Entertainment
Dave Specter | Chicago Blues
Food & Beverage
Steep Ravine Brewing Company
Fluffy Bunny
Yana’s Speakeasy
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
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
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
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!
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
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
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
Sidewalk Sale
The Highland Park Chamber of Commerce presents:
Sidewalk Sale
July 25 & 26 | 10 AM - 5 PM
Downtown Highland Park
More info coming soon!
Food Truck Thursdays
JULY 24 LINEUP
4:30 PM - 5:45 PM | Despina Pafralides | Bluegrass folk
6 PM - 8:30 PM | Jared Rabin Band | Local Americana rock’n’roll
Food Truck Thursdays
June 5 - September 18 | 4:30 PM - Dusk
Jens Jensen Park | 540 Roger Williams Ave.
Mark your calendars: Food Truck Thursdays returns to the Ravinia District this summer, June 5 through September 18, at Jens Jensen Park! Savor fresh flavors from a variety of food trucks, including Highland Park vendors Abigail’s American Bistro, Indus Progressive Indian, Michael’s Grill & Salad Bar, Shaevitz Kosher Market & BBQ, and Steep Ravine Brewing Company while enjoying warm summer evenings and dancing to great music every Thursday night, 4:30 PM to dusk in the Ravinia District!
We can’t imagine a better way to spend a summer evening than good friends, good food, and of course, great music.
FEATURED TRUCKS
Bumbu Roux, Chessie Struck, Chicago Lunch Box, Chill’s Italian Ice, Cousins Maine Lobster, Culinary Gangster Glenview, Frankie Da Pizza Dude, Goodstuff Eats, Hawaiian Food Truck, Hello Boba Truck, Kona Ice, La Cocinita, Limoni Belli, Little Louies, Mamalicous Cooking, Maiztify, My Funnel Truck, Nettle Creek Foods, Royal Ice Cream, San Judas Food Truck, Sausage Fest Truck, Taco Motora, Taste Greek Good, Tievoli Pizza Bar, and Yum Dum Truck
Food Truck Thursdays are presented by the City of Highland Park and the Ravinia District Special Service Area 17 property owners, and are managed by Bensidoun USA. The music for Food Truck Thursdays is coordinated by Life Rhythms, Inc., and is co-sponsored by the Highland Park Community Foundation. Additional event sponsors include Wayfarer Theaters. For more information on how to be a part of the 2025 event season as a participating or sponsoring business, please contact the Ravinia District’s event management team, Ripple Public Relations, info@ripplepublicrelations.com, or call 847.432.6000.
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
Downtown Concerts at Port Clinton
The City of Highland Park’s Downtown Event Series presents:
Downtown Concerts at Port Clinton
July 18 | 6 PM - 8 PM
Port Clinton Square | 600 Central Ave.
What’s better than a summertime Friday evening? A summertime Friday evening with a concert! The City of Highland Park is excited to announce the return of free, City-sponsored Downtown concerts at Port Clinton Square (600 Central Ave.) on select Friday evenings July 11 through September 26. Bring a lawn chair and kickoff your weekend with live music from a diverse range of artists and genres including: folk, reggae, blues, soul, classic rock, Latin, and more.
JULY 18 LINEUP
Entertainment
Urban Roots Band | Reggae
Food & Beverage
Yana’s Speakeasy
Fluffy Bunny
Food Truck Thursdays
JULY 17 LINEUP
4:30 PM - 5:45 PM | Jeanie B! | Children’s entertainer
6 PM - 8:30 PM | The Ravinia Ramblers | Local family-friendly rock’n’roll
Food Truck Thursdays
June 5 - September 18 | 4:30 PM - Dusk
Jens Jensen Park | 540 Roger Williams Ave.
Mark your calendars: Food Truck Thursdays returns to the Ravinia District this summer, June 5 through September 18, at Jens Jensen Park! Savor fresh flavors from a variety of food trucks, including Highland Park vendors Abigail’s American Bistro, Indus Progressive Indian, Michael’s Grill & Salad Bar, Shaevitz Kosher Market & BBQ, and Steep Ravine Brewing Company while enjoying warm summer evenings and dancing to great music every Thursday night, 4:30 PM to dusk in the Ravinia District!
We can’t imagine a better way to spend a summer evening than good friends, good food, and of course, great music.
FEATURED TRUCKS
Bumbu Roux, Chessie Struck, Chicago Lunch Box, Chill’s Italian Ice, Cousins Maine Lobster, Culinary Gangster Glenview, Frankie Da Pizza Dude, Goodstuff Eats, Hawaiian Food Truck, Hello Boba Truck, Kona Ice, La Cocinita, Limoni Belli, Little Louies, Mamalicous Cooking, Maiztify, My Funnel Truck, Nettle Creek Foods, Royal Ice Cream, San Judas Food Truck, Sausage Fest Truck, Taco Motora, Taste Greek Good, Tievoli Pizza Bar, and Yum Dum Truck
Food Truck Thursdays are presented by the City of Highland Park and the Ravinia District Special Service Area 17 property owners, and are managed by Bensidoun USA. The music for Food Truck Thursdays is coordinated by Life Rhythms, Inc., and is co-sponsored by the Highland Park Community Foundation. Additional event sponsors include Wayfarer Theaters. For more information on how to be a part of the 2025 event season as a participating or sponsoring business, please contact the Ravinia District’s event management team, Ripple Public Relations, info@ripplepublicrelations.com, or call 847.432.6000.
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
Downtown Concerts at Port Clinton
The City of Highland Park’s Downtown Event Series presents:
Downtown Concerts at Port Clinton
July 11 | 6 PM - 8 PM
Port Clinton Square | 600 Central Ave.
What’s better than a summertime Friday evening? A summertime Friday evening with a concert! The City of Highland Park is excited to announce the return of free, City-sponsored Downtown concerts at Port Clinton Square (600 Central Ave.) on select Friday evenings July 11 through September 26. Bring a lawn chair and kickoff your weekend with live music from a diverse range of artists and genres including: folk, reggae, blues, soul, classic rock, Latin, and more.
JULY 11 LINEUP
Entertainment
The Oh Yeahs | Acoustic Vocal Trio
Food & Beverage
Steep Ravine Brewing Company
Fluffy Bunny
Awesome Mini Donuts
Food Truck Thursdays - Broadway Nite
JULY 10 LINEUP
4:30 PM - Dusk | Selections from Rent by Highland Park Players, selections from Wicked by Children’s Theatre Co., & selections from Hairspray by Uptown Music Theater
Dusk | Special screening of Hairspray in the park sponsored by the Park District of Highland Park
Food Truck Thursdays - Broadway Nite
July 10 | 4:30 PM - Dusk
Jens Jensen Park | 540 Roger Williams Ave.
Mark your calendars: Food Truck Thursdays returns to the Ravinia District this summer, June 5 through September 18, at Jens Jensen Park! Savor fresh flavors from a variety of food trucks, including Highland Park vendors Abigail’s American Bistro, Indus Progressive Indian, Michael’s Grill & Salad Bar, Shaevitz Kosher Market & BBQ, and Steep Ravine Brewing Company while enjoying warm summer evenings and dancing to great music every Thursday night, 4:30 PM to dusk in the Ravinia District!
We can’t imagine a better way to spend a summer evening than good friends, good food, and of course, great music.
FEATURED TRUCKS
Bumbu Roux, Chessie Struck, Chicago Lunch Box, Chill’s Italian Ice, Cousins Maine Lobster, Culinary Gangster Glenview, Frankie Da Pizza Dude, Goodstuff Eats, Hawaiian Food Truck, Hello Boba Truck, Kona Ice, La Cocinita, Limoni Belli, Little Louies, Mamalicous Cooking, Maiztify, My Funnel Truck, Nettle Creek Foods, Royal Ice Cream, San Judas Food Truck, Sausage Fest Truck, Taco Motora, Taste Greek Good, Tievoli Pizza Bar, and Yum Dum Truck
Food Truck Thursdays are presented by the City of Highland Park and the Ravinia District Special Service Area 17 property owners, and are managed by Bensidoun USA. The music for Food Truck Thursdays is coordinated by Life Rhythms, Inc., and is co-sponsored by the Highland Park Community Foundation. Additional event sponsors include Wayfarer Theaters. For more information on how to be a part of the 2025 event season as a participating or sponsoring business, please contact the Ravinia District’s event management team, Ripple Public Relations, info@ripplepublicrelations.com, or call 847.432.6000.
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
Independence Day Parade
The City of Highland Park presents:
Independence Day Parade: Dream Team
July 4 | 11 AM
Downtown Highland Park
What’s your dream team?
This year’s parade theme is a celebration of all that brings us together. Whether that’s family or friends, sports, dance, faith, community or neighborhood, tap into team spirit as Highland Park’s community-focused parade returns to Downtown Highland Park! The parade will follow the same route as 2024, beginning at First St. & Laurel Ave. and progressing through Downtown Highland Park to Sunset Woods Park. Parade participants and attendees are encouraged to wear team jerseys and apparel, and floats will celebrate the colors and mascots of favorite teams and organizations.
There will not be a City or Park District-sponsored evening event on Independence Day.
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
Bitter Jester Music Festival Grand Finale
Bitter Jester Foundation for the Arts presents
Bitter Jester Music Festival Grand Finale
June 28 | 2 PM - 10:30 PM
Second St. from Central Ave. to Laurel Ave.
Looking for something fun to do on the weekend? How about live music near you…
The Grand Finale concert will be co-emceed by NPR's Peter Sagal (host of "Wait Wait... Don't Tell Me!") and Bitter Jester's Nicolas DeGrazia (Emmy-winning Producer/Director). Come out and meet Peter in person while you discover your next favorite band! Twelve musical acts from half a dozen states will be featured.
Eight musical acts from half a dozen states compete alongside four Showcase Artists. Kick back with a cool drink from Steep Ravine Brewing Company or a great bite to eat from Judy’s Pizza, BWB Shakes, or Curt’s Cafe while you enjoy this FREE, vibrant, and family-friendly show. You’ll be sure to discover your next favorite band or solo artist to add to your personal playlists after the festival!
FINALE LINEUP
In Competition:
Cabin Fever (NY)
Charlieboy (WI)
Exit 122 (IL)
Meera Raphael (RI)
Patches & Albo (IL)
Platinum Moon (NY)
Tikimen of Berlin (MI)
Zeke Rowan (MI)
Featured Showcases:
Crowd Vulture (IL)
North Grove (IL)
The Orchids (IL)
Rae (TN)
Wine Stroll
The Highland Park Chamber of Commerce presents:
Wine Stroll
June 26 | 5 PM - 7:30 PM
Check in at First Bank of Highland Park | 1835 First St.
Stroll the streets of downtown Highland Park and visit the participating businesses while sipping, shopping, and savoring!
Be a part of one of Highland Park’s most anticipated community events! The Highland Park Wine Stroll draws residents and visitors alike to our vibrant downtown for an evening of wine tastings, shopping, and fun! As a participating business, you’ll have the unique opportunity to showcase your brand, drive foot traffic, and connect with new customers in a fun and festive atmosphere.
Food Truck Thursdays
JUNE 26 LINEUP
4:30 PM - 5:45 PM | Angry Ankles | Gypsy jazz for kids
6 PM - 8:30 PM | Nasty Snacks | 8-piece funk band with horns
Food Truck Thursdays
June 5 - September 18 | 4:30 PM - Dusk
Jens Jensen Park | 540 Roger Williams Ave.
Mark your calendars: Food Truck Thursdays returns to the Ravinia District this summer, June 5 through September 18, at Jens Jensen Park! Savor fresh flavors from a variety of food trucks, including Highland Park vendors Abigail’s American Bistro, Indus Progressive Indian, Michael’s Grill & Salad Bar, Shaevitz Kosher Market & BBQ, and Steep Ravine Brewing Company while enjoying warm summer evenings and dancing to great music every Thursday night, 4:30 PM to dusk in the Ravinia District!
We can’t imagine a better way to spend a summer evening than good friends, good food, and of course, great music.
FEATURED TRUCKS
Bumbu Roux, Chessie Struck, Chicago Lunch Box, Chill’s Italian Ice, Cousins Maine Lobster, Culinary Gangster Glenview, Frankie Da Pizza Dude, Goodstuff Eats, Hawaiian Food Truck, Hello Boba Truck, Kona Ice, La Cocinita, Limoni Belli, Little Louies, Mamalicous Cooking, Maiztify, My Funnel Truck, Nettle Creek Foods, Royal Ice Cream, San Judas Food Truck, Sausage Fest Truck, Taco Motora, Taste Greek Good, Tievoli Pizza Bar, and Yum Dum Truck
Food Truck Thursdays are presented by the City of Highland Park and the Ravinia District Special Service Area 17 property owners, and are managed by Bensidoun USA. The music for Food Truck Thursdays is coordinated by Life Rhythms, Inc., and is co-sponsored by the Highland Park Community Foundation. Additional event sponsors include Wayfarer Theaters. For more information on how to be a part of the 2025 event season as a participating or sponsoring business, please contact the Ravinia District’s event management team, Ripple Public Relations, info@ripplepublicrelations.com, or call 847.432.6000.
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
Taste of Highland Park
Taste of Highland Park
JUNE 20 & 21 | 5 PM - 10 PM BOTH DAYS
PORT CLINTON SQUARE | 600 CENTRAL AVE.
The Taste of Highland Park is downtown Highland Park’s premier dining and music festival. Mark your calendars for 2025’s event: Friday, June 20 and Saturday, June 21 from 5 PM - 10 PM both nights, at Port Clinton Square (600 Central Ave.).
Food Truck Thursdays
JUNE 19 LINEUP
4:30 PM - 5:45 PM | Cary Cohen’s Grateful Jazz Band | Instrumental jazz for kids
6 PM - 8:30 PM | Saturday June Band | Jazz
Food Truck Thursdays
June 5 - September 18 | 4:30 PM - Dusk
Jens Jensen Park | 540 Roger Williams Ave.
Mark your calendars: Food Truck Thursdays returns to the Ravinia District this summer, June 5 through September 18, at Jens Jensen Park! Savor fresh flavors from a variety of food trucks, including Highland Park vendors Abigail’s American Bistro, Indus Progressive Indian, Michael’s Grill & Salad Bar, Shaevitz Kosher Market & BBQ, and Steep Ravine Brewing Company while enjoying warm summer evenings and dancing to great music every Thursday night, 4:30 PM to dusk in the Ravinia District!
We can’t imagine a better way to spend a summer evening than good friends, good food, and of course, great music.
FEATURED TRUCKS
Bumbu Roux, Chessie Struck, Chicago Lunch Box, Chill’s Italian Ice, Cousins Maine Lobster, Culinary Gangster Glenview, Frankie Da Pizza Dude, Goodstuff Eats, Hawaiian Food Truck, Hello Boba Truck, Kona Ice, La Cocinita, Limoni Belli, Little Louies, Mamalicous Cooking, Maiztify, My Funnel Truck, Nettle Creek Foods, Royal Ice Cream, San Judas Food Truck, Sausage Fest Truck, Taco Motora, Taste Greek Good, Tievoli Pizza Bar, and Yum Dum Truck
Food Truck Thursdays are presented by the City of Highland Park and the Ravinia District Special Service Area 17 property owners, and are managed by Bensidoun USA. The music for Food Truck Thursdays is coordinated by Life Rhythms, Inc., and is co-sponsored by the Highland Park Community Foundation. Additional event sponsors include Wayfarer Theaters. For more information on how to be a part of the 2025 event season as a participating or sponsoring business, please contact the Ravinia District’s event management team, Ripple Public Relations, info@ripplepublicrelations.com, or call 847.432.6000.
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
Bitter Jester Music Festival Preliminary Concert - Night 4
Bitter Jester Foundation for the Arts presents
Bitter Jester Music Festival Preliminary Concert Night 4
June 14 | 5:30 PM - 10:30 PM
Port Clinton Square | 600 Central Ave.
Looking for something fun to do on the weekend? How about live music near you…
Each week, six bands/solo artists from across the Midwest and beyond battle for a spot in the June 28, 2025, Grand Finale for a $2,000 cash prize, gear, incredible additional performance opportunities, and the title of Grand Champion! One BJMF Finalist will be selected to open for a National Headliner at Ravinia Festival in 2026!
These FREE concerts are vibrant and fun variety acts that the whole family can enjoy. You’ll be sure to discover your next favorite band or solo artist to add to your personal playlists after the festival!
NIGHT 4 LINEUP:
• Belle Vista (Showcase)
• Cabin Fever
• Control the Sound (Showcase)
• Crowd Vulture
• Elle of the Wilds (Guest Artist)
• Exit 122
• The Orchids
• Party Hat Club
• rae
• TUMI (Guest Artist)
Arts on Sheridan
Amdur Productions presents
Arts on Sheridan
June 14 - June 15 | 10 AM - 5 PM
Downtown Highland Park | Sheridan Rd. from The Art Center to Central Ave., & Central Ave. from Chase Bank (corner of Central & St. Johns) to Public Parking at 442 & 421 Central Ave.
Plan Your Day at Arts on Sheridan in Highland Park!
This June 14 and 15, join us at Arts on Sheridan, a brand new art festival in beautiful Highland Park, IL! Stroll through East Highland Park and explore a curated selection of art from talented artists across all mediums. Whether you're looking for the perfect gift for Father's Day or want to enjoy a summer day surrounded by beautiful art, Arts on Sheridan is the place for you. Don't miss out on this exciting new festival in this beautiful North Shore community! With a Kids Art Zone, live music, food + drink and Live Art Demos, there is something for the whole family all weekend long!
Bitter Jester Music Festival Preliminary Concert - Night 3
Bitter Jester Foundation for the Arts presents
Bitter Jester Music Festival Preliminary Concert Night 3
June 13 | 5:30 PM - 10:30 PM
Port Clinton Square | 600 Central Ave.
Looking for something fun to do on the weekend? How about live music near you…
Each week, six bands/solo artists from across the Midwest and beyond battle for a spot in the June 28, 2025, Grand Finale for a $2,000 cash prize, gear, incredible additional performance opportunities, and the title of Grand Champion! One BJMF Finalist will be selected to open for a National Headliner at Ravinia Festival in 2026!
These FREE concerts are vibrant and fun variety acts that the whole family can enjoy. You’ll be sure to discover your next favorite band or solo artist to add to your personal playlists after the festival!
NIGHT 3 LINEUP:
• Candy Cigarette (Showcase)
• Christine Compall (Guest Artist)
• Floryence (Guest Artist)
• Lackadays
• Monica James (Guest Artist)
• Plastic Summer
• Platinum Moon
• The Regulars
• Sierra Sikora
• STARLESS (Showcase)
• ZEKE ROWAN
Food Truck Thursdays - Taylor Swift Nite
JUNE 12 LINEUP
4:30 PM - 8:30 PM | Attention Swifties! Get ready for all your favorite Taylor Swift tunes with a live DJ and Taylor Swift impersonator, Shake it Off. Represent your favorite “era” and take part in tons of family fun.
Sponsored by Banner Kitchen & Bath
Food Truck Thursdays in the City of Highland Park’s Ravinia District is calling all friends in their “Swiftie Era” to a special Taylor Swift theme night on June 12, from 4:30 PM - 8:30 PM. Attendees are invited to come out dressed ‘fearless and flawless,’ enjoy a high-energy dance party with a live DJ spinning Taylor’s hits, and sing along with Taylor Swift impersonator Shake It Off. Sponsored by Banner Kitchen & Bath Showroom, Taylor Swift Night will exceed your “Wildest Dreams,” complete with a Swiftie Selfie Station courtesy of Sugaring NYC. You’ll want to “Stay, Stay, Stay” all night long!
Beginning June 5, the opening night of Food Truck Thursdays, the public can get ‘in tune with Taylor’ and partake in a Name That Taylor Tune tour through the Ravinia District. Various Ravinia District businesses will have iconic Taylor Swift lyrics posted in their windows. “Fearless” players will find clues throughout the district in order to guess the name of the associated Taylor Tune and fill in the “Blank Space” on their game sheets. Players can pick up their Name That Taylor Tune game sheet inside participating businesses. Completed forms should be dropped off at the Food Truck Thursdays’ theme night activity booth on June 12 (Taylor Swift Night) to be entered into a drawing. The winner will be “Enchanted” to receive a $50 gift card to the participating Ravinia District business of their choice.
PARTICIPATING BUSINESSES
From June 5 - June 12, the following Ravinia District businesses will have “Name That Taylor Tune” lyrics displayed in their windows. Download the game sheet and start playing!
Anuk Nails, Astra Coffee Roasters, BWB Shakes, The Chunky Scone, Dana Reed Designs, Fluffy Bunny, Furry Finesse, Happi Sushi, Jeff Cohen Photography, Joe Palminteri - State Farm Insurance, Mil Colibris Bakery + Cafe, Piero’s Pizza, PT2, Ravinia Barbers, Ravinia Books, Antiques, Etc., Ravinia Bridal, Ravinia Custom Closets, Salon Raquel, Steep Ravine Brewing Company, Uncommon Fitness, Viaggio, Vintage Rescue, and Yana’s Speakeasy
Food Truck Thursdays: Taylor Swift Nite
June 12 | 4:30 PM - Dusk
Jens Jensen Park | 540 Roger Williams Ave.
Mark your calendars: Food Truck Thursdays returns to the Ravinia District this summer, June 5 through September 18, at Jens Jensen Park! Savor fresh flavors from a variety of food trucks, including Highland Park vendors Abigail’s American Bistro, Indus Progressive Indian, Michael’s Grill & Salad Bar, Shaevitz Kosher Market & BBQ, and Steep Ravine Brewing Company while enjoying warm summer evenings and dancing to great music every Thursday night, 4:30 PM to dusk in the Ravinia District!
We can’t imagine a better way to spend a summer evening than good friends, good food, and of course, great music.
FEATURED TRUCKS
Bumbu Roux, Chessie Struck, Chicago Lunch Box, Chill’s Italian Ice, Cousins Maine Lobster, Culinary Gangster Glenview, Frankie Da Pizza Dude, Goodstuff Eats, Hawaiian Food Truck, Hello Boba Truck, Kona Ice, La Cocinita, Limoni Belli, Little Louies, Mamalicous Cooking, Maiztify, My Funnel Truck, Nettle Creek Foods, Royal Ice Cream, San Judas Food Truck, Sausage Fest Truck, Taco Motora, Taste Greek Good, Tievoli Pizza Bar, and Yum Dum Truck
Food Truck Thursdays are presented by the City of Highland Park and the Ravinia District Special Service Area 17 property owners, and are managed by Bensidoun USA. The music for Food Truck Thursdays is coordinated by Life Rhythms, Inc., and is co-sponsored by the Highland Park Community Foundation. Additional event sponsors include Wayfarer Theaters. For more information on how to be a part of the 2025 event season as a participating or sponsoring business, please contact the Ravinia District’s event management team, Ripple Public Relations, info@ripplepublicrelations.com, or call 847.432.6000.
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
Bitter Jester Music Festival Preliminary Concert - Night 2
Bitter Jester Foundation for the Arts presents
Bitter Jester Music Festival Preliminary Concert Night 2
June 7 | 5:30 PM - 10:30 PM
Port Clinton Square | 600 Central Ave.
Looking for something fun to do on the weekend? How about live music near you…
Each week, six bands/solo artists from across the Midwest and beyond battle for a spot in the June 28, 2025, Grand Finale for a $2,000 cash prize, gear, incredible additional performance opportunities, and the title of Grand Champion! One BJMF Finalist will be selected to open for a National Headliner at Ravinia Festival in 2026!
These FREE concerts are vibrant and fun variety acts that the whole family can enjoy. You’ll be sure to discover your next favorite band or solo artist to add to your personal playlists after the festival!
NIGHT 2 LINEUP:
• The 1-800s
• The Broken Vinyls
• Claire-Mckenna
• Holden Garcia (Guest Artist)
• NewClearFusion (Showcase)
• Nikki Rodrigues (Guest Artist)
• Patches & Albo
• Superimposed
• Tikimen of Berlin
• Trial and Error (Showcase)
• Violet Clare (Guest Artist)
Cops & Bobbers
The City of Highland Park, the Highland Park Police Department, and the Park District of Highland Park present:
Cops & Bobbers
June 7 | 9 AM - 11 AM
The Preserve of Highland Park | 1207 Park Ave. W.
Grab your gear and join the City of Highland Park Police Department for a morning of FREE fishing and fun! Officers and Park District of Highland Park staff will be onsite to help bait and reel in your biggest catch. Participants with the largest fish caught in their age group will win a prize!
Ages 15 & under and adults. No fishing license required.
Bitter Jester Music Festival Preliminary Concert - Night 1
Bitter Jester Foundation for the Arts presents
Bitter Jester Music Festival Preliminary Concert Night 1
June 6 | 5:30 PM - 10:30 PM
Port Clinton Square | 600 Central Ave.
Looking for something fun to do on the weekend? How about live music near you…
Each week, six bands/solo artists from across the Midwest and beyond battle for a spot in the June 28, 2025, Grand Finale for a $2,000 cash prize, gear, incredible additional performance opportunities, and the title of Grand Champion! One BJMF Finalist will be selected to open for a National Headliner at Ravinia Festival in 2026!
These FREE concerts are vibrant and fun variety acts that the whole family can enjoy. You’ll be sure to discover your next favorite band or solo artist to add to your personal playlists after the festival!
NIGHT 1 LINEUP:
• Ayden Holt (Guest Artist)
• BYRON (Guest Artist)
• Charlieboy
• The Coves
• Earl Hester (Showcase)
• Holden Garcia (Guest Artist)
• Meera Raphael
• North Grove
• The Reys
• Silver October (Guest Artist, MUSIC @ 5:15pm)
• Speedbump
• State of Youth (Showcase)
Food Truck Thursdays
JUNE 5 LINEUP
4:30 PM - 5:45 PM | Ben Tatar & the Tatar Tots | Children’s entertainer
6 PM - 8:30 PM | Radio Free Honduras | Latin rock
Food Truck Thursdays
June 5 - September 18 | 4:30 PM - Dusk
Jens Jensen Park | 540 Roger Williams Ave.
Mark your calendars: Food Truck Thursdays returns to the Ravinia District this summer, June 5 through September 18, at Jens Jensen Park! Savor fresh flavors from a variety of food trucks, including Highland Park vendors Abigail’s American Bistro, Indus Progressive Indian, Michael’s Grill & Salad Bar, Shaevitz Kosher Market & BBQ, and Steep Ravine Brewing Company while enjoying warm summer evenings and dancing to great music every Thursday night, 4:30 PM to dusk in the Ravinia District!
We can’t imagine a better way to spend a summer evening than good friends, good food, and of course, great music.
FEATURED TRUCKS
Bumbu Roux, Chessie Struck, Chicago Lunch Box, Chill’s Italian Ice, Cousins Maine Lobster, Culinary Gangster Glenview, Frankie Da Pizza Dude, Goodstuff Eats, Hawaiian Food Truck, Hello Boba Truck, Kona Ice, La Cocinita, Limoni Belli, Little Louies, Mamalicous Cooking, Maiztify, My Funnel Truck, Nettle Creek Foods, Royal Ice Cream, San Judas Food Truck, Sausage Fest Truck, Taco Motora, Taste Greek Good, Tievoli Pizza Bar, and Yum Dum Truck
Food Truck Thursdays are presented by the City of Highland Park and the Ravinia District Special Service Area 17 property owners, and are managed by Bensidoun USA. The music for Food Truck Thursdays is coordinated by Life Rhythms, Inc., and is co-sponsored by the Highland Park Community Foundation. Additional event sponsors include Wayfarer Theaters. For more information on how to be a part of the 2025 event season as a participating or sponsoring business, please contact the Ravinia District’s event management team, Ripple Public Relations, info@ripplepublicrelations.com, or call 847.432.6000.
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
Women-Owned Business Whistle Stop Trolley Tour
Whistle-Stop Trolley Tour of Women-Owned Businesses in Downtown HP
MAY 8 | 5 PM - 8:30 PM
Downtown Highland Park
Mark your calendars for May 8! All aboard the Whistle-Stop Trolley Tour of Women-Owned Businesses throughout Downtown Highland Park! Hop on and off of charming trolleys while visiting over 30 shops and boutiques - all owned and operated by inspiring women entrepreneurs. Discover unique products, take part in demos, and find specials and promotions along the way. Maps will be available with your Passport Badge. Limited tickets available for this first-time event and can be purchased for $20 in advance.
STOPS: ABC Design Jewelers, AcuCare NorthShore Wellness, Adesso, Atelier by elliestyled, Bar Method, Central Boutique, Dayhouse Coworking, ENAZ, Eye Magic, Face Foundrié, Gordon Salon, Harper+Ash, Indus Progressive Indian, Joan Barry Hair Designers, La Taquiza, Laughlin Gallery, Love That Spice, Onward Physical Therapy Chicago-Northshore, Pets4Life, Pulling Down the Moon, Rock N Rags, ROSS’s, Sage Counsel Family Law & Estate Planning, Secret World Books, Soulshine Boutique & Healing Sanctuary, Sprout Kids, Style Shack, Sugaring NYC, Therapeutic Kneads, & YogaSix
Passport Badges will be available for early pickup during business hours day of the event at Face Foundrié, ENAZ, and Rock N Rags.
Trolleys will run from 5 PM -8 PM. Doors open for the afterparty at Atelier by elliestyled (1900 Sheridan Rd.) at 7:30 PM.
The Golden Gala - Senior Prom
The Golden Gala - Senior Prom
Highland Park Senior Center | 1201 Park Ave. W | 847.432.4110
MAY 3 | 5 PM - 7:30 PM | $10 | REGISTER BY APR. 28
The Highland Park High School Class of 2027 invites you to join them for a night at the Prom!
Enjoy a fabulous evening of dinner, dancing, and entertainment. Guests will enjoy a buffet dinner and a sweet table with home-baked goodies. The HPHS DJ Club will provide music, and some of the high school’s most talented artists will perform throughout the evening. The student hosts are planning an enchanting evening of glitter and gold, and they will be dressed up... ready to serve, ready to dance, and ready to entertain! This amazing event is open to all community members, aged 50+.
Call 847.432.4110 to reserve your spot before April 28.
This event is sponsored by Arbor Terrace Highland Park.