Entertainment Lineup at The Lot
The City is thrilled to announce the broad entertainment lineup for featured events at The Lot, the City’s alfresco dining and entertainment destination. The 2023 calendar of events includes the return of the Taste of Highland Park (with Bitter Jester Music Festival Grand Finale Concert), two Vintage Markets, World Music Fest, Vintage Car Show, Oktoberfest and an expanded two-night Stews & Brews.
Kicking off in June and running through the fall, the City will host this series of seven free events at The Lot, an outdoor multipurpose entertainment space located at the northwest corner of Central and St. Johns in downtown Highland Park.
With an eclectic lineup of music, food and themed events planned, The Lot’s 2023 season features the following musical acts:
Vintage Market: Sunday, June 11, 11 AM-4 PM
In addition to 50+ of the best vintage dealers from Chicago and the Midwest at this one-of-a-kind Vintage Market on the North Shore, this event will feature originals and classic rock covers from Saturday June Band and classic rock covers from Slavin & Trudell to take attendees back in time!
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.
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.
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 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.
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 including: internationally known DJ Taz Rashid, Chicago’s Indian Arabic Flamenco full experience Surabhi Ensemble, a global music and dance collective, The “World’s Loudest Folk Band,” The Tossers, and The Rumble featuring Chief Joseph Boudreaux and their classic Mardi Gras sound.
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 food, libations and live authentic 60’s garage rock from The Wayouts and The Four C Notes, recreating the music of Frankie Valli and the Four Seasons.
Oktoberfest: Saturday, September 30, 12-10 PM
This seasonal event will feature traditional Oktoberfest food and drinks with a beer garden, games, themed contests (including the beer stein holding contest!) along with headlining live music from Die Musikmeisters, a lively German band performing a diverse repertoire of German polkas and waltzes.
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 food, libations and live entertainment including the sounds of hot club jazz from Bowmanville Swing and the first and only female-fronted yacht rock cover band, the Yacht Rock-ettes.
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 including: Barry and The Fountains, Win Noll & The Rockin’ Souls, Ivy Ford and Billy Branch and the Sons of Blues.
About The Lot
The Lot is the City of Highland Park’s alfresco dining and entertainment space located at 523 Central Ave. at the intersection of St. Johns and Central Avenues in the heart of downtown Highland Park. From specialty markets to unique dining, family friendly entertainment, weekend concerts and food fests, there’s something for everyone this season at The Lot with music and entertainment as a big draw to get them there.
Ample parking surrounds the Lot, including nearby surface lots, a two-level parking deck south of Central on First St. and St. Johns, and the Port Clinton parking garage. The City encourages guests to use non-motorized transportation where available. Bike racks are available at The Lot and in the immediate vicinity. Information about parking in the City of Highland Park is available at cityhpil.com/parking.
Because The Lot is not conducive to animals, attendees are requested to not bring pets to events at The Lot.
Events at The Lot are presented by the City of Highland Park with the generous support of: Porsche Audi Exchange, First Bank of Highland Park, Highland Park Bank & Trust, Highland Park Community Foundation, Sunset Foods, Walled Lake Planning & Wealth Management, Wayfarer Theaters, Baird & Warner, Gearhead Outfitters and PromptMed Urgent Care.
Learn more about plans for The Lot and view the entire season schedule at enjoyhighlandpark.com/thelot. For more information about the City of Highland Park, please contact Amanda Bennett, communications manager, at abennett@cityhpil.com.