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Festival season is here! From Food Truck Thursdays to the Taste of Highland Park, Arts on Sheridan, the Bitter Jester Music Festival and beyond... Plus find shopping, dining, and even more great live events. Get all the details and more in this week's edition of the Weekender.
📸: The BBQ Pit has been serving up delicious barbecue since 1978! Learn more in this week's Business Spotlight.
589 Elm Pl. / 847.432.6393
Explore more delicious dining with our dining guide.
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BITTER JESTER FOUNDATION FOR THE ARTS
20th Annual Bitter Jester Music Festival
PRELIMINARY CONCERTS - JUN. 5, JUN. 6, JUN. 12, & JUN. 13 | 5:30 PM - 10:30 PM
GRAND FINALE - JUN. 27 | 2 PM - 10 PM
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The Bitter Jester Music Festival is celebrating 20 years! That's two decades of fabulous free concerts featuring some of the most talented youth artists from across the nation performing in the heart of Downtown Highland Park.
What started as a small "battle of the bands" for local performers has evolved into the nation's largest live festival showcasing emerging artists under the age of 25. Hundreds of performers from all across the nation have applied, now it's time to enjoy the music as the top 40 acts from over a dozen states compete for almost $15,000 in cash and other prizes. With food, craft beer, wine, great coffee, and free parking, the Bitter Jester Music Festival is a must-see event!
Multiple genres will be featured each night during the four preliminary concerts taking place on June 5, 6, 12, and 13. A winner will be selected at each of the four preliminary concerts with four additional "Wild Cards" selected by festival producers. Those eight acts will then compete head-to-head at a Grand Finale Concert co-hosted by Nicolas DeGrazia (an Emmy-winning TV director and HP native - the festival's founder) and Peter Sagal (host of NPR's Wait Wait... Don't Tell Me!) on June 27. Come to the Finale for the music and stay to hear Peter interview performers after their sets!
As 101.9 The Mix put it: "It's an incredible concert with a bunch of future headliners!" So check out some of your next favorite bands and be able to say "I saw them when..."
Port Clinton Square - 600 Central Ave.
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STEEP RAVINE BREWING COMPANY
Late Nights
& Live Music
THURS. - SAT. | OPEN TIL 11 PM
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Not ready for your night on the town to end? Steep Ravine Brewing Company is now open until 11 PM Thursdays, Fridays, and Saturdays. Celebrate this Saturday, June 6 beginning at 7:30 PM with a live performance from the Willows Band.
582 Roger Williams Ave. / 847.780.8127
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RAVINIA FESTIVAL
Alisa Weilerstein & Inon Barnatan
JUN. 7 | 1:30 PM
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“One of the most characterful cellists around” (The Times) and “one of the most admired pianists of his generation” (New York Times) come together at Ravinia Festival's Martin Theatre on June 7 for an afternoon of sweeping emotion and virtuosity. Cellist Alisa Weilerstein and pianist Inon Barnatan, longtime collaborators who have recorded three albums together, bring their shared musical insight to a program of passion and color, featuring Falla’s Suite populaire espagnole, several Shostakovich preludes, and sonatas by Chopin and Rachmaninoff.
$43 - $66
Martin Theatre / 201 Ravinia Park Rd.
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Grab your pole and and head to the fishing hole! The Highland Park Police Department and the Park District of Highland Park are teaming up to help you bait and reel in your biggest catch. Cops & Bobbers will take place on June 6 from 9 AM - 11 AM at The Preserve of Highland Park. Those who catch the biggest fish in each age group (5 & younger, 6 - 8 years, 9 - 12 years, and 13 - 15 years) will win an exciting prize. Participants are encouraged to bring their own fishing gear, however, limited loaner equipment and bait will be available. Cops & Bobbers is free, though registration is required. No fishing license is necessary.
The Preserve of Highland Park - 1207 Park Ave. W
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FT. SHERIDAN HISTORICAL SOCIETY
Ft. Sheridan Nat'l Cemetery Walking Tour
JUN. 7 | 10 AM, 11:15 AM, 12:30 PM, 1:45 PM, & 3 PM
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The Fort Sheridan Historical Society will host a walking tour of the Fort Sheridan National Cemetery on Sunday, June 7. Step back in time to learn the story of this honored resting place as well as those of some of the soldiers interred within. The cemetery was established in 1889 and holds well over a century of history.
$20 Adults / $10 Students & FSHS Members
Ft. Sheridan National Cemetery - Entrance off of Vattman Rd.
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OVER THE TOP
Elliott Lauren Trunk Show & Sale
THROUGH JUN. 6
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Does your summer wardrobe need a refresh? Head to Over The Top through June 6 and discover new styles during the Elliott Lauren Trunk Show. Plus, take 10% off of all orders and in-stock items during the show!
1866 First St. / 847.433.3150
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ENJOY HIGHLAND PARK
Taste of Highland Park
JUN. 19 | 5 PM - 10 PM & JUN. 20 3 PM - 10 PM | FREE
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The City of Highland Park is bringing the ultimate outdoor entertainment and dining experience to Downtown Highland Park with the Taste of Highland Park June 19 from 5 PM - 10 PM & June 20 from 3 PM - 10 PM. Spanning Central Avenue, from Second St. to the Metra Tracks just west of St. Johns Ave., and in Port Clinton Square (600 Central Ave.), sample over a dozen local food and beverage vendors and get a taste of what sets Highland Park’s restaurant scene apart on Chicago’s North Shore.
Get ready for more food, more music, and even more fun for 2026!
New for 2026: Enhance your experience with air conditioned seating & dining areas, as well as an all-new photography exhibit showcasing the winners of the Capture the Heart of Highland Park photography contest. Plus, enjoy an exclusive America250 performance celebrating our shared values and Juneteenth, special children-focused programming, and an energetic set by an alum of Highland Park’s very own Bitter Jester Music Festival, now in its 20th year. Lastly, raise your glasses and toast "Here's to the Night" on Saturday, June 20 with internationally-touring headliners, Eve 6!
Port Clinton Square - 600 Central Ave.
| FRIDAY, JUNE 19 with DJ MADRID | |
5 PM - 5:30 PM | Beloved hometown favorites Highland Park Players kick off the Taste of Highland Park with selections from their upcoming production of Beautiful: The Carole King Musical running July 17-26, 2026.
5:45 PM - 6:30 PM | Celebrate America’s semiquincentennial and recognize Juneteenth with a vibrant dance and choral experience led by Waukegan-based ALATS Dance Company. ALATS Dance Company, founded by Highland Park High School alum Rev. Cory Ratliff, will be joined by MC4 and DKeyz.
7 PM - 8 PM | Next up is Rumor Hazit, a high-energy cover band known for crowd-pleasing hits spanning rock, pop, and throwback favorites that keep audiences singing along.
8:30 PM - 10 PM | Friday’s headliners, the All American Throwbacks, are a dynamic tribute band delivering nostalgic rock and pop anthems from the ‘80s, ‘90s, and 2000s with powerhouse vocals and big-stage energy.
| SATURDAY, JUNE 20 with DJ JULIAN | |
3 PM - 5:15 PM | Introducing, brand new for 2026, children’s hours at the Taste of Highland Park! Enjoy complimentary face painting, airbrush tattoos, meet popular characters Ariel, Jessie, and Woody, and sing and dance along to Mary Macaroni (3 PM - 3:30 PM) and Laura Doherty (4 PM - 4:30 PM). Highland Park’s very own Uptown Music Theater will perform a professional sneak-peek mini concert featuring songs from the upcoming production of Disney’s The Little Mermaid running July 18 - August 2. As a bonus, the actors playing the lead roles of Ariel, Ursula, and Sebastian will autograph mini-posters for kids after the performance! While the entire Taste of Highland Park is family-friendly, this portion is specifically geared toward children.
5:30 PM - 6:30 PM | 2026 marks the 20th anniversary of the Bitter Jester Music Festival right here in Highland Park. In honor of this incredible achievement, and ahead of the Bitter Jester grand finale in Downtown Highland Park on June 27, special guests and BJMF alumni Charlieboy will perform.
7 PM - 8 PM | Popular acoustic rock duo, Mike & Joe, is known for tight harmonies and energetic covers of classic and modern rock favorites. They’re sure to get the crowd moving!
8:30 PM - 10 PM | Headliner Eve 6, a nationally-recognized alternative-rock band best known for high-energy live performances, will close out the evening with chart-topping hits including “Inside Out,” “Here’s to the Night,” “Promise,” and more.
| PARTICIPATING FOOD & BEVERAGE VENDORS | BWB Shakes, Cafe Dacha, DeNucci's, Harmony Coffee Bar (NEW FOR 2026!), Highland Bar & Kitchen (NEW FOR 2026!), Indus Progressive Indian, Judy's Pizza, Las Torres Mexican Restaurant (NEW FOR 2026!), Lynfred Winery, Michael's Grill & Salad Bar, Steep Ravine Brewing Company, and Tamales | THANK YOU TO THIS YEAR'S SPONSORS! | | |
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SECRET WORLD BOOKS
Meet the Author: Boman Desai
JUN. 9 | 7 PM
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Join Secret World Books on June 9 to celebrate author Boman Desai and his latest novel, Brahms Comes to Dinner, winner of the 2025 Nicholas Schaffner Award for Music in Literature!
Synopsis: Set in Germany in the mid-19th century, the novel tells the story of renowned composer Johannes Brahms and his lifelong friendship and love for Clara Schumann, widow of Robert Schumann. The Schumanns were early champions of the young composer, and the novel brings to life the interaction among the three.
FREE
1774 Second St. / 847.469.4875
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WAYFARER THEATERS
Punch Lines & Popcorn
JUN. 10 | 7 PM - 8:30 PM
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Punch Lines & Popcorn is the newest comedy series to hit the North Shore. Join host Chris Trani and the best stand up comedians in the Chicagoland area at Wayfarer Theaters on June 10. Enjoy a free popcorn with your ticket to this family-friendly, hilarious show.
$15
1850 Second St. / 872.873.1030
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Family owned and operated since 1978, The BBQ Pit is known for home-cooked comfort food and a classic personal touch. From midwestern BBQ to steaks, fish, salads, and sandwiches, the BBQ Pit serves up delicious food in a warm and friendly environment.
Originally located on First St., the address is the only notable change in the nearly 50 years since The BBQ Pit opened. Despite having been recognized by publications such as The Chicago Tribune, the Chicago Sun-Times, Chicago Magazine, and North Shore Magazine, The BBQ Pit is most proud of the relationships that have been established with customers.
Enjoy a family recipe at one of Highland Park's longest-standing establishments!
589 Elm Pl. / 847.432.6393 / bbqpitribhouse.com
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DINX SOCIAL CLUB
Summer Kids Camp
JUN. 8 - JUN. 12
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The ever-popular Day Off Kids Camp is back at DINX Social Club from June 8 - June 12! Kids will enjoy pickleball, golf, SNAX, and unforgettable moments. Morning (10 AM - 12 PM) and afternoon (1 PM - 3 PM) sessions are available. Spots are limited, so grab yours now!
$55 Members / $65 Nonmembers
1931 Skokie Valley Rd. / 847.926.7191
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TAMALES
Lunchtime Special
THROUGH JUN. 15
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Tamales is now open for lunch on Mondays, Thursdays, Fridays, and Saturdays at 11:30 AM! To celebrate, Tamales is giving the people who make Highland Park so amazing a special lunchtime discount. Through June 15, show proof that you live, work, or shop in Highland Park and Tamales will take 15% off of your check.
493 Central Ave. / 847.433.4070
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RAVINIA DISTRICT
Food Truck Thursdays
THURSDAYS THROUGH SEPT. 3 | 4:30 PM - DUSK | FREE
| Food Truck Thursdays in the Ravinia District is in full swing! A whole season of delicious meals and fantastic live music awaits! Don't miss the next event on June 11 at Jens Jensen Park (540 Roger Williams Ave.). Grab your crew and get ready to make memories this summer. | |
5 PM - 5:50 PM | Ravinia Festival’s Jazz Scholars - Student jazz band
6 PM - 8:30 PM | Nasty Snacks - Nine-piece funk & soul
| Abigail's American Bistro, Indus Progressive Indian, Michael's Grill & Salad Bar, Shaevitz Kosher Market, Steep Ravine Brewing Company, Chicago Lunchbox, Hello Boba, Jesse's Gelato, Kona Ice, Limoni Belli Neapolitan Pizzeria, Royal Ice Cream, Smeauxk BBQ, Snowie Shaved Ice Delights, Taco Motora, Tievoli Pizza Truck, The Yellow Duck Truck, Pucker Up Confectionary, La Cocinita, Little Louie's, Tapioca Loca, Cheesie's Truck, & Cluckers | |
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 City contractor Life Rhythms, Inc., and is co-sponsored by the Highland Park Community Foundation.
Jens Jensen Park - 540 Roger Williams Ave.
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LYNFRED WINERY
Tuesday Takeout Takeover
TUESDAYS IN JUNE | 3 PM - 7:15 PM
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Have you ever wished you had the perfect wine to pair with a delicious takeout meal from your favorite Highland Park restaurant? Check out Tuesday Takeout Takeover at Lynfred Winery! Each Tuesday in June, stop by Lynfred with your same-day receipt from a Highland Park restaurant. Lynfred will provide pairing suggestions and take $2 off the purchase price of your wine.
1823 St. Johns Ave. / 847.780.3853
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MATCHMAKER BOOKSHOP
Love Letters Book Club
JUN. 16 | 6:30 PM - 7:30 PM
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If you're a fan of romance novels, you're invited to join Matchmaker Bookshop for the monthly Love Letters Book Club on June 16! June's book for discussion is The Paris Match by Kate Clayborn, conveniently available to purchase in-store.
FREE
1891 Second St. / 847.926.7554
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RAVINIA FARMERS MARKET
48th Annual Ravinia Farmers Market
WEDNESDAYS, THROUGH OCT. 28 | 7 AM - 1 PM
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The Ravinia Farmers Market returned for its 48th season this weel, bringing fresh local foods, live music and community fun to Jens Jensen Park every Wednesday from 7 AM - 1 PM through October 28.
Featuring more than 35 vendors throughout the season, the market offers a wide variety of seasonal produce, artisan food products, specialty prepared foods, flowers and plants, local health and wellness products, handmade goods, community organizations and more. Weekly live music and rotating pop-up activities add to the relaxed, welcoming atmosphere that has made the Ravinia Farmers Market a longtime Highland Park tradition.
Set beneath the trees in Jens Jensen Park, the market has become a weekly gathering place where families, friends and neighbors can shop, support local farmers and businesses, enjoy ready-made foods, listen to live music and linger in the park on a summer morning.
Returning this season is free Yoga in the Park with Lori Fink of YogaSix Highland Park each week at 11 AM. New this year, David Derdiger of Open Flow Acupuncture will offer free weekly Qigong classes at 9:30 AM throughout June, July and August. This class will introduce participants to fluid movement, standing meditation and wellness practices designed to support balance and well-being. All wellness activities take place on the lawn beneath the trees in Jens Jensen Park.
Additional complimentary family-friendly activities throughout the season will include balloon art beginning June 3, as well as select face painting dates and other entertainment TBA, all presented by Chicago-based entertainment company Share Happiness. Also beginning June 3, market visitors can enter weekly free prize drawings featuring Ravinia Festival concert tickets on select weeks, along with giveaways and prizes from local businesses and community partners.
Weekly music at the market is provided by Life Rhythms, and sponsored by the Highland Park Community Foundation. Additional market sponsors and supporters include the City of Highland Park, the Park District of Highland Park, the Ravinia Neighbors Association, Presence, Wayfarer Theaters, and Keyth Security.
Jens Jensen Park - 540 Roger Williams Ave.
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HIGHLAND PARK POETRY
Poetry Reading
& Open Mic
JUN. 13 | 4 PM - 6 PM
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Batter up! This month, Highland Park Poetry shines the spotlight on The Songs of Summer: Poems about Baseball, an anthology edited by Tom Erickson and Ed Werstein. Tom and Ed will be joined by several local contributors to the anthology all sharing their poems about baseball. An open mic will follow the featured readings. Come a few minutes early to sign up for the line-up. Poets may bring up to three short poems to share. The fun will take place at Secret World Books on June 13.
Secret World Books - 1774 Second St.
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AMDUR PRODUCTIONS
Arts on Sheridan
JUN. 13 & JUN. 14 | 10 AM - 5 PM | FREE
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This June 13 and 14, join Amdur Productions at the second annual Arts on Sheridan! Stroll through the art and design district in east Highland Park and explore a curated selection of art from talented artists across all mediums. Don’t miss out on this exciting art festival! With a Kids Art Zone, live music, food and beverage, and live art demonstrations, there is something for the whole family all weekend long!
Sheridan Rd., Downtown Highland Park
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MCDONALD'S & HIGHLAND PARK POLICE DEPARTMENT
Cone With A Cop
JUN. 13 | 11 AM - 1 PM
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McDonald's is partnering with the Highland Park Police Department to ensure every kid's summer gets a sweet start! Head to McDonald's on June 13 and meet the men and women of the Highland Park Police Department, take photos in a real police vehicle, and best of all, enjoy a sweet, FREE, vanilla cone!
FREE
1988 First St. / 224.365.5759
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INDUS PROGRESSIVE INDIAN
Celebrate Dad
with Indus
JUN. 21
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Celebrate Dad at Indus Progressive Indian! Indus will be open for both lunch and dinner on Father's Day, June 21, serving all of Dad’s Indus favorites including the popular Bhoomi Burger, Club Sandwich, Naan Wrap, Masala Brisket, and so much more! Dad’s favorite drinks including whiskey and beer flights will also be available.
617 Central Ave. / 312.282.8064
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CITY OF HIGHLAND PARK
Be A Part of This Year's Independence Day Parade!
OPEN THROUGH JUNE 5
| Calling all Highland Parkers! Share your American story and love of history at The City's Independence Day parade. Help bring the America250 theme to life with patriotic and historical floats. Celebrate our shared history and illustrate what America means to you! Whether through characters like Uncle Sam or Rosie the Riveter, floats that showcase the history of HP businesses or organizations, or entries that celebrate a special decade or time in our history, the sky's the limit! Individuals, families, and groups of friends and neighbors are encouraged to apply. Applications for the Independence Day parade are available now, and are due by June 5. | | |
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THE ART CENTER & LIFE RHYTHMS
Community
Drum Circle
JUN. 14 | 10: 30 AM - 11:30 AM
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Create your own beat and uncover your rhythm with The Art Center and Life Rhythms on June 14 for a free community drum circle. Discover Afro-Cuban, Brazilian, and West African rhythms, then add in hybrid hand drumming techniques for an unforgettable experience.
FREE
1957 Sheridan Rd. / 847.432.1888
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PARK DISTRICT OF HIGHLAND PARK
Heller Discovery Hour
JUN. 10 | 11:30 AM - 12:30 AM
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Need something to do mid-week this summer? The Park District has you covered! Drop by Heller Nature Center every-other Wednesday from 11:30 AM - 12 PM for Heller Discovery Hour! Meet a Heller Nature Center naturalist (and maybe even an animal or two!) and learn fascinating facts about local wildlife! Each session offers a new theme or creature, making every visit a little different!
FREE
Heller Nature Center - 2821 Ridge Rd.
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HIGHLAND PARK PUBLIC LIBRARY
Puzzle Exchange / Intercambio de Rompecabezas
JUN. 6 | 11 AM - 1 PM
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Have you completed all the puzzles in your collection? Bring them to the Library to trade on June 6!
¿Has completado todos los rompecabezas en tu colección? ¡Tráelos a la biblioteca para un intercambio!
494 Laurel Ave. / 847.432.0216
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