City of Highland Park Announces 2023 Festival Lineup at The Lot

Highland Park, Illinois – The City of Highland Park is thrilled to announce the 2023 event line-up at The Lot, Downtown Highland Park’s alfresco dining and entertainment destination launched June 2022. 

Kicking off in June and running through the fall, the City will host a series of seven free events at The Lot, the City’s outdoor multipurpose entertainment space located at the northwest corner of Central and St. Johns in downtown Highland Park. Planned as a seasonal installation from 2022-2023, the City is exploring opportunities for a possible permanent buildout in 2025.

With an eclectic lineup of music, food and themed events planned, The Lot’s 2023 season includes:

• Vintage Market: Sunday, June 11, 11 AM-4 PM

Attendees can expect 50+ of the best vintage dealers from Chicago and the Midwest at this one-of-a-kind Vintage Market on the North Shore while browsing a range of unique items, enjoying live entertainment, food and libations.

• Taste of Highland Park:  Friday, June 23, 5-10 PM & Saturday, June 24, 12-10 PM

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! 

• Bitter Jester Music Festival Grand Finale Concert: Sunday, June 25, 12 – 8 PM

The Midwest's largest professional "battle-of-the-bands" style concert and competition series featuring bands and solo performers that 101.9 The Mix calls "Future Headliners!" The summer-long Festival culminates in this celebration of talented new artists 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 from multiple states.  Bands compete to win a $2,000 cash prize sponsored by First Bank of Highland Park and the title of Grand Champion. A "Live at Bitter Jester" album will also be recorded (and available for pre-sale) at The Lot that day!

• World Music and Food Fest:  Saturday, July 15, 12-10 PM

Diverse music and food bring a multitude of global flavors and experiences in a fun, family-friendly festival atmosphere! Attendees will savor a variety of food options from sweets and snacks to appetizers and entrees, all while enjoying live music featuring the sounds of India, Mexico, Celtic countries and more!

• Vintage Car Show:  Saturday, September 9, 12-4 PM

Attendees will spend the afternoon in downtown Highland Park perusing an eclectic display of vintage automobiles, both antique and classics up to the early 1980’s, while enjoying live music, food, and libations. 

• Oktoberfest:  Saturday, September 30, 12-10 PM

This seasonal event will feature traditional Oktoberfest food, drink and beer garden along with headlining live music, games and other on-site activities including themed contests - including the return of the beer stein holding contest!

• Vintage Market (Part 2): Sunday, October 8, 11 AM-4 PM

Attendees can expect 50+ of the best vintage dealers from Chicago and the Midwest at this one-of-a-kind Vintage Market on the North Shore while browsing a range of unique items, enjoying live entertainment, food and libations.

• Stews & Brews (and Blues!):  October 13 & 14, 5-9 PM

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.

From specialty markets to unique dining, family friendly entertainment, weekend concerts and food fests, there’s something for everyone this season at The Lot. 

For more information on how to be a part of the 2023 event season at The Lot as a participating or sponsoring business, please contact the City’s event management team, Ripple Public Relations, info@ripplepublicrelations.com, or call 847.432.6000. Learn more about plans for The Lot at enjoyhighlandpark.com/thelot. For more information about the City of Highland Park, please contact Amanda Bennett, communications manager, at abennett@cityhpil.com.