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
French Market
Sundays, June 9 - September 29, 10 AM - 3 PM
Browse an array of artisan and specialty food vendors from around Chicagoland, showcasing a unique tableau of products and wares.
French Market
Sundays, June 9 - September 29, 10 AM - 3 PM
Browse an array of artisan and specialty food vendors from around Chicagoland, showcasing a unique tableau of products and wares.
French Market
Sundays, June 9 - September 29, 10 AM - 3 PM
Browse an array of artisan and specialty food vendors from around Chicagoland, showcasing a unique tableau of products and wares.
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
French Market
Sundays, June 9 - September 29, 10 AM - 3 PM
Browse an array of artisan and specialty food vendors from around Chicagoland, showcasing a unique tableau of products and wares.
French Market
Sundays, June 9 - September 29, 10 AM - 3 PM
Browse an array of artisan and specialty food vendors from around Chicagoland, showcasing a unique tableau of products and wares.
French Market
Sundays, June 9 - September 29, 10 AM - 3 PM
Browse an array of artisan and specialty food vendors from around Chicagoland, showcasing a unique tableau of products and wares.
French Market
Sundays, June 9 - September 29, 10 AM - 3 PM
Browse an array of artisan and specialty food vendors from around Chicagoland, showcasing a unique tableau of products and wares.
French Market
Sundays, June 9 - September 29, 10 AM - 3 PM
Browse an array of artisan and specialty food vendors from around Chicagoland, showcasing a unique tableau of products and wares.
French Market
Sundays, June 9 - September 29, 10 AM - 3 PM
Browse an array of artisan and specialty food vendors from around Chicagoland, showcasing a unique tableau of products and wares.
French Market
Sundays, June 9 - September 29, 10 AM - 3 PM
Browse an array of artisan and specialty food vendors from around Chicagoland, showcasing a unique tableau of products and wares.
*This Sunday’s event will run concurrent with the Vintage Car Show taking place along St. Johns Avenue, parallel to The Lot.
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!
French Market
Sundays, June 9 - September 29, 10 AM - 3 PM
Browse an array of artisan and specialty food vendors from around Chicagoland, showcasing a unique tableau of products and wares.
French Market
Sundays, June 9 - September 29, 10 AM - 3 PM
Browse an array of artisan and specialty food vendors from around Chicagoland, showcasing a unique tableau of products and wares.
French Market
Sundays, June 9 - September 29, 10 AM - 3 PM
Browse an array of artisan and specialty food vendors from around Chicagoland, showcasing a unique tableau of products and wares.
French Market
Sundays, June 9 - September 29, 10 AM - 3 PM
Browse an array of artisan and specialty food vendors from around Chicagoland, showcasing a unique tableau of products and wares.
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.
French Market
Sundays, June 9 - September 29, 10 AM - 3 PM
Browse an array of artisan and specialty food vendors from around Chicagoland, showcasing a unique tableau of products and wares.
French Market
Sundays, June 9 - September 29, 10 AM - 3 PM
Browse an array of artisan and specialty food vendors from around Chicagoland, showcasing a unique tableau of products and wares.
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.
French Market
Sundays, June 9 - September 29, 10 AM - 3 PM
Browse an array of artisan and specialty food vendors from around Chicagoland, showcasing a unique tableau of products and wares.
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!
Takeout Tuesday: Finale!
Every Tuesday night from July 12 - August 30, come out and play at The Lot! Grab takeout from a local restaurant or enjoy light bites and treats from pop-up restaurants! Additionally, The Art Center of Highland Park will host weekly crafts/activities throughout Take-Out Tuesdays. Music, games, food, creativity - what’s not to love?
August 30: Finale!
We’ll be saying good-bye to our Take-Out Tuesday season fondly with special offerings throughout!
Takeout Tuesday: Local Performance Showcase
Every Tuesday night from July 12 - August 30, come out and play at The Lot! Grab takeout from a local restaurant or enjoy light bites and treats from pop-up restaurants! Additionally, The Art Center of Highland Park will host weekly crafts/activities throughout Take-Out Tuesdays. Music, games, food, creativity - what’s not to love?
August 23: Local Performance Showcase
Some of the area's finest musical and entertainment acts will be onsite to wow attendees in this encouraging showcase to support all performers.
Veg Fest
Explore veg options from restaurants throughout the Chicago area along with music, meditation/yoga sessions and cooking demos.
Takeout Tuesday: Fashion Night
Every Tuesday night from July 12 - August 30, come out and play at The Lot! Grab takeout from a local restaurant or enjoy light bites and treats from pop-up restaurants! Additionally, The Art Center of Highland Park will host weekly crafts/activities throughout Take-Out Tuesdays. Music, games, food, creativity - what’s not to love?
August 16: Fashion Night
In time for back to school fashions, we’ll have retailers onsite to show off the latest trends!
Takeout Tuesday: Home Refresh Night
Every Tuesday night from July 12 - August 30, come out and play at The Lot! Grab takeout from a local restaurant or enjoy light bites and treats from pop-up restaurants! Additionally, The Art Center of Highland Park will host weekly crafts/activities throughout Take-Out Tuesdays. Music, games, food, creativity - what’s not to love?
August 9: Home Refresh Night
We have a plethora of beautiful home decor establishments, landscape companies, interior designers and more in Highland Park. Come out to see what small (and big!) changes you can make to beautify your home.
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.
Takeout Tuesday: Party Planning Night
Every Tuesday night from July 12 - August 30, come out and play at The Lot! Grab takeout from a local restaurant or enjoy light bites and treats from pop-up restaurants! Additionally, The Art Center of Highland Park will host weekly crafts/activities throughout Take-Out Tuesdays. Music, games, food, creativity - what’s not to love?
August 2: Party Planning Night
Want to support local businesses when planning your next party? We’ll have Downtown HP businesses onsite to make your lives easier!
Takeout Tuesday: Fitness & Wellness Night
Every Tuesday night from July 12 - August 30, come out and play at The Lot! Grab takeout from a local restaurant or enjoy light bites and treats from pop-up restaurants! Additionally, The Art Center of Highland Park will host weekly crafts/activities throughout Take-Out Tuesdays. Music, games, food, creativity - what’s not to love?
July 26: Fitness & Wellness Night
Calling all exercise buffs! Come try snippets of workouts from some of Downtown Highland Park’s finest fitness studios while also experiencing a sampling of services from wellness studios.
Takeout Tuesday: Beauty Night
Every Tuesday night from July 12 - August 30, come out and play at The Lot! Grab takeout from a local restaurant or enjoy light bites and treats from pop-up restaurants! Additionally, The Art Center of Highland Park will host weekly crafts/activities throughout Take-Out Tuesdays. Music, games, food, creativity - what’s not to love?
July 19: Beauty Night
Studios throughout Downtown HP are invited to showcase their offerings with complimentary services to community members for a gorgeous night out!
World Music Fest
Diverse music & food bring together a multitude of tastes and experiences in a fun, festival atmosphere! Stay tuned for more information.
Takeout Tuesday: Game Night
Every Tuesday night from July 12 - August 30, come out and play at The Lot! Grab takeout from a local restaurant or enjoy light bites and treats from pop-up restaurants! Additionally, The Art Center of Highland Park will host weekly crafts/activities throughout Take-Out Tuesdays. Music, games, food, creativity - what’s not to love?
July 12: Game Night
Kids and adults alike will enjoy games such as cornhole, bocce, oversized games such as Connect 4. Community members are encouraged to bring their own mah jong or canasta set and enjoy an alfresco game at The Lot.
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.
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.