Calendar
What’s Happening?
There’s always something to see or do in Highland Park! Check out our calendar to plan your next visit.
Featured Events
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.
Event Listings
Taste of Highland Park
The City of Highland Park is bringing the ultimate lineup of entertainment and dining to The Lot (525 Central Ave.) with its opening festival, the Taste of Highland Park. Internationally-touring platinum artists Dishwalla and Spin Doctors headline, globally-recognized DJ Madrid returns as The Lot’s resident DJ, and 13 premier food vendors are ready to satisfy every palate!
An unbelievable lineup of nationally-recognized bands will take the stage over the course of two evenings, June 21 & 22, from 5 PM - 10 PM:
FRIDAY, JUNE 21
• 5 PM - 6:15 PM: The Taste of Highland Park commences with the Chicago-based Jaren Grey Band’s unique brand of heartland rock covers and original songs
• 7 PM - 8 PM: Up next is famed 90s rock band Nine Days, known for their memorable hit “Absolutely (Story of a Girl)”
• 8:30 PM -10 PM: Platinum-selling band Dishwalla, famously known for fan-favorite and Billboard Award “Best Rock Song” of 1996 “Counting Blue Cars,” will wrap up evening one of the Taste
SATURDAY, JUNE 22
• 5 PM - 5:30 PM: Highland Park’s very own Uptown Music Theater opens evening two of the Taste with a Broadway Favorites Concert. Get a sneak peek of their upcoming production of Les Misérables; opening July 2024 and benefitting the Highland Park Community Foundation
• 6 PM - 7:15 PM: Local favorites Serendipity will bring their high-energy, iconic playlist of hits from the 70s, 80s, and today to ignite the crowd
• 8 PM - 10 PM: The Taste of Highland Park will conclude with alternative rock band Spin Doctors, best known for chart-topping hits including “Little Miss Can’t Be Wrong” and the Grammy nominated song “Two Princes”
On-site vendors will bring a wide variety of food and drink including Mexican, Indian, American, Venezuelan, vegan/vegetarian, sweet treats, grilled items, pizza, wine, beer, cocktails, and more. Participating food vendors include Bella Ru Catering, BWB Shakes, Cafe Dacha, Curt’s Café, Indus Progressive Indian Dining, Judy’s Pizza, La Taquiza HP, Lynfred Winery, Michael’s Grill & Salad Bar, Pixca, Ravinia Brewing Company, Sugarcoated, and Tamales. Libations will be available for those 21 and older!
Bitter Jester Music Festival Finale
Saturday, June 29, Times TBA
It’s more than a competition, it’s a destination event, complete with music, food, and beverages.12 bands showcase their virtuosity at The Lot, competing for the winner’s title. Many BJMF alumni have gone on to perform on Late Night with Seth Myers, Saturday Night Live, and American Jukebox, as well as at Lollapalooza, Riot Fest, South by Southwest, and Ravinia Festival.
Get more info on the festival here.
*This event is a privately organized festival, hosted by the City of Highland Park
Vintage Auto Show
Peruse a fabulous array of vintage vehicles, right on St. Johns Avenue while enjoying live music, food, and beverages. Then, head inside The Lot to check out The French Market, happening simultaneously!
Decades
Saturday, September 14, 10 AM – 10 PM, The Lot opens at Noon
Fantastic headlining music from the 70s, 80s, and 90s brings together decades of music fans. Travel back in time to experience the sounds, tastes, and trends from these three decades through a selection of live performances and food and beverage vendors. A “Decades of Music” scavenger hunt through downtown Highland Park businesses will round out this event.
Oktoberfest
Saturday, September 28, 12 PM – 10 PM
Start the day with traditional Oktoberfest fun: music, food, beverages, and family-focused activities. At 5 PM, we switch up the vibe with a headline band.
Scarecrow Fest & Walk
Saturday, October 19, 12 - 5 PM
Celebrate Fall with scarecrow-themed family fun, kids’ actives, and seasonal decor at The Lot. Take a stroll through downtown Highland Park’s “Scarecrow Walk” to see festive scarecrows decorated by local businesses. Head back to The Lot to vote for best in show.
Stews & Brews (& Booze & Blues)
Combining two Midwestern favorites: comfort foods and beverages. Stay cozy with fire pits, heaters, hearty food, and great live music. The evening culminates with a People's Choice competition for the favorite Stew and Brew. This event is sure to warm the hearts and souls of all who attend!
Stews & Brews
Combining two Midwestern comfort foods and beverages, this event will warm the hearts of all that attend!
Stews & Brews
This cool weather event will get attendees warmed up with a variety of hardy stick—to-the-ribs stews including chili, jambalaya, Hungarian goulash, chicken pot pie and more. All kinds of brews will be available too, from craft beer, spiced ciders and wines, to hot toddies, hot chocolate and kombucha! A stellar line-up of blues artists will grace the stage as well.
Vintage Market
Antique and vintage vendors with unique items for sale, along with seasonal bites and beverages.
Oktoberfest
Beer garden with great music and delicious, traditional bites to bring the community together! Prost!
Vintage Car Show
Vintage cars with light bites and background music. Check out the cars, then head to your favorite Highland Park restaurant for dinner.
World Music & Food Fest
Diverse music & food bring together a multitude of tastes and experiences in a fun, festival atmosphere! Stay tuned for more information.
Bitter Jester Music Festival Grand Finale Concert
The Midwest's largest professional "battle-of-the-bands" style concert and competition series will feature bands and solo performers that 101.9 The Mix calls "Future Headliners!" and will be announced after the summer-long Festival culminates as part of the Taste of Highland Park weekend. The Grand Finale Concert will feature a wide variety of food and drinks vendors all day long as well as a dozen musical acts TBD from multiple states.
Taste of Highland Park
This fan favorite at The Lot will showcase a variety of delicious cuisines and beverages. A fantastic weekend lineup of live music will include nationally recognized headliners and on-site fun for the entire family.
Friday will kick-off with a set by former resident DJ for Virgin Megastore Chicago, DJ Madrid, who will also spinning all night long in between sets performed by a cappella’s favorite boy band, Radius Vocals, and the nation’s #1 Yacht Rock band, Yachtley Crew. Saturday boasts the following acts including: the jam band ensemble of Marcus Rezak Band featuring Shred is Dead and Gumbo, roots singer/songwriter Joseph Huber, Grammy nominated bluegrass musicians Sister Sadie Band, The Complete Beatles Tribute Band American English, and Chicago’s own rock band The Ides of March powered by Grammy winner Jim Peterik.
Taste of Highland Park
This fan favorite at The Lot will showcase a variety of delicious cuisines and beverages. A fantastic weekend lineup of live music will include nationally recognized headliners and on-site fun for the entire family.
Friday will kick-off with a set by former resident DJ for Virgin Megastore Chicago, DJ Madrid, who will also spinning all night long in between sets performed by a cappella’s favorite boy band, Radius Vocals, and the nation’s #1 Yacht Rock band, Yachtley Crew. Saturday boasts the following acts including: the jam band ensemble of Marcus Rezak Band featuring Shred is Dead and Gumbo, roots singer/songwriter Joseph Huber, Grammy nominated bluegrass musicians Sister Sadie Band, The Complete Beatles Tribute Band American English, and Chicago’s own rock band The Ides of March powered by Grammy winner Jim Peterik.
Vintage Market
Antique and vintage vendors with unique items for sale, along with seasonal bites and beverages.
Stews & Brews
Combining two Midwestern comfort foods and beverages, this event will warm the hearts of all that attend!
Vintage Market
Antique and vintage vendors with unique items for sale, along with seasonal bites and beverages.
Oktoberfest
Beer garden with great music and delicious, traditional bites to bring the community together! Prost!
Oktoberfest
Beer garden with great music and delicious, traditional bites to bring the community together! Prost!
Literary Fest
Featured author talk, performances, book & record dealers, scheduled readings and more!
Food Truck Thursdays
We can’t imagine a better way to spend a summer evening than good friends, good food and of course, great music. Food Truck Thursdays are returning to the Ravinia District this summer, Thursdays from June 2 - September 8, 4:30 PM to dusk in Jens Jensen Park.
September 8:
Plotkin & Rabin Duo
Food Truck Thursdays
We can’t imagine a better way to spend a summer evening than good friends, good food and of course, great music. Food Truck Thursdays are returning to the Ravinia District this summer, Thursdays from June 2 - September 8, 4:30 PM to dusk in Jens Jensen Park.
September 1:
Mojo 49
Food Truck Thursdays
We can’t imagine a better way to spend a summer evening than good friends, good food and of course, great music. Food Truck Thursdays are returning to the Ravinia District this summer, Thursdays from June 2 - September 8, 4:30 PM to dusk in Jens Jensen Park.
August 25:
Jon Ladeau
Veg Fest
Explore veg options from restaurants throughout the Chicago area along with music, meditation/yoga sessions and cooking demos.
Food Truck Thursdays
We can’t imagine a better way to spend a summer evening than good friends, good food and of course, great music. Food Truck Thursdays are returning to the Ravinia District this summer, Thursdays from June 2 - September 8, 4:30 PM to dusk in Jens Jensen Park.
August 18: Disco Night
Food Truck Thursdays
We can’t imagine a better way to spend a summer evening than good friends, good food and of course, great music. Food Truck Thursdays are returning to the Ravinia District this summer, Thursdays from June 2 - September 8, 4:30 PM to dusk in Jens Jensen Park.
August 11:
The Basement Band
Vintage Car Show
Vintage cars with light bites and background music. Check out the cars, then head to your favorite Highland Park restaurant for dinner.
Food Truck Thursdays
We can’t imagine a better way to spend a summer evening than good friends, good food and of course, great music. Food Truck Thursdays are returning to the Ravinia District this summer, Thursdays from June 2 - September 8, 4:30 PM to dusk in Jens Jensen Park.
August 4:
Food Truck Thursdays
We can’t imagine a better way to spend a summer evening than good friends, good food and of course, great music. Food Truck Thursdays are returning to the Ravinia District this summer, Thursdays from June 2 - September 8, 4:30 PM to dusk in Jens Jensen Park.
July 28: New Orleans Night
Food Truck Thursdays
We can’t imagine a better way to spend a summer evening than good friends, good food and of course, great music. Food Truck Thursdays are returning to the Ravinia District this summer, Thursdays from June 2 - September 8, 4:30 PM to dusk in Jens Jensen Park.
July 21:
World Music Fest
Diverse music & food bring together a multitude of tastes and experiences in a fun, festival atmosphere! Stay tuned for more information.
Food Truck Thursdays
We can’t imagine a better way to spend a summer evening than good friends, good food and of course, great music. Food Truck Thursdays are returning to the Ravinia District this summer, Thursdays from June 2 - September 8, 4:30 PM to dusk in Jens Jensen Park.
July 14:
Food Truck Thursdays
We can’t imagine a better way to spend a summer evening than good friends, good food and of course, great music. Food Truck Thursdays are returning to the Ravinia District this summer, Thursdays from June 2 - September 8, 4:30 PM to dusk in Jens Jensen Park.
July 7:
Albie Powers
Heiwa Bando
Food Truck Thursdays
We can’t imagine a better way to spend a summer evening than good friends, good food and of course, great music. Food Truck Thursdays are returning to the Ravinia District this summer, Thursdays from June 2 - September 8, 4:30 PM to dusk in Jens Jensen Park.
June 30: Beatles Night
Dr. Mark & The Sutures
Taste of Highland Park
Savor the taste of summer with cooking demos and special dishes from Highland Park chefs coupled with exceptional music.
Attendees will savor a variety of American, Asian, Barbecue, Cajun, Italian, Mediterranean, Mexican, Vegan/Vegetarian, sweet treats and more from Bluegrass, BWB Shakes, Judy’s Pizza, Madame Zuzu’s, Michael’s Grill & Salad Bar, Pixca, Poke Burrito, Ravinia Brewing Company, Sally’s Nuts, Tamales, Bella Ru Catering and Uncle Tannous. Libations will be available for those 21 and older!
The fest will also feature a fantastic lineup of live music with headlining performances from the Freddy Jones Band and Yachtley Crew. The Freddy Jones Band, currently touring to promote the 30th anniversary of their hit “In a Daydream,” will rock the opening night crowd on Friday, June 24. On Saturday, June 25, recognized nationally as “The Titans of Soft Rock”, LA-based Yachtley Crew will take the stage with their great sound and high-energy show filled with timeless 70’s and 80’s hits.