Festivals on Chicago’s North Shore 2024 | Chicago North Shore Moms

Let’s do this! Here’s your Chicago North Shore Moms roundup of summer and fall festivals 2024 on the North Shore! Just click on the links below for details.



May 2024 Festivals
  • May First Friday in Hubbard Woods: A Chocolate Walk: May 3, 2024 @4PM to 7PM Green Bay Road, Winnetka, IL. On May 3rd, the Hubbard Woods Design District will host its first, First Friday of 2024! Along with live music throughout the district, participating stores will be offering refreshments, including deliciously decadent chocolates.
  • Northbrook Art in the Park: May 11 and May 12, 2024 10AM-5PM. Make your masterpiece at our live painting class, or plan a stop at the Kid’s Creation Station.
  • Rocky’s (the cow) 2nd Birthday Party at Lambs Farm: May 18, 2024 @12PM to 2PM, Farmyard 14245 W Rockland Road, Libertyville, IL. Rocky is turning 2! Join us on Saturday, May 18 from 12pm to 2pm as we celebrate our favorite White Park cow!
  • Touch a Truck Wilmette: May 18, 2024 @10AM to 12PM, Centennial Parking Lot. Touch A Truck puts kids in the driver’s seat! Join the Wilmette Park District, Village of Wilmette and more during this FREE and unique opportunity to explore trucks of all types all in one place.
  • Glenview Car Show: May 19, 2024 @11AM to 2PM, 974 Railroad Ave. Third Charity Exotic Car Show 11am – 2pm benefiting the 100 Club of Illinois. Free admission to all spectators.
  • Lake County Food Truck Festival: May 24, 2024 @5PM to 9PM, The Lake County Food Truck Festival is returning to the Lake County Fairgrounds – with over 40 food vendors! On Friday, May 24, from 4pm to 9pm, join us for a food-filled extravaganza that is sure to satisfy your taste buds.
June 2024 Festivals
  • Deerfield Art Festival: June 1 and June 2, 2024 10AM-5PM, 821 Park Ave Deerfield, IL . The Deerfield Art Festival is filling Park Avenue with 100 original artists on June 1-2! Start your family or friend’s day downtown with coffee and breakfast, then soak in the creativity of the fest!
  • Lake Forest Concerts in the Park: June 6, 2024 @6:30PM, Northcroft Park. Kick off your summer with free live music in Northcroft Park! Music and fun for the whole family.
  • Fred Jackson Golf Classic: June 7, 2024 @11:15AM, Deerpath Golf Course. Join us for the 23rd Anniversary of The Fred Jackson Golf Classic! This is one of the Friends of Lake Forest Parks and Recreation Foundation’s largest fundraisers. This fun-filled event features 18 holes plus a cart, lunch and beverages, awards, and Mayor’s Cup. Open to the public.
  • June First Friday in Hubbard Woods: June 7, 2024 @4PM to 7PM, Green Bay Road, Winnetka, IL. On June 7th, the Hubbard Woods Design District will host its monthly First Friday event. Along with live music throughout the district, participating stores will be offering refreshments. It’s a great opportunity to stop, browse, and shop!
  • Winnetka Children’s Fair 77 Anniversary: June 7 to 8, 2024 @2PM to 8PM, 800 Pine Street, Winnetka, IL 60093. The Winnetka Children’s Fair will celebrate its 77th anniversary June 7-8, 2024! The Fair is hosted and organized by the Winnetka Community Nursery School Board of Directors, with aid from hundreds of local volunteers and the support of several area businesses.
  • Winnetka Music Festival: June 14 5PM to 11PM and June 15, 2024 12pm to 1PM Winnetka Music Festival 620 Lincoln Ave Winnetka, IL 60093. Winnetka Music festival returns to the Northshore with two days of music and interactive experiences for the whole family, alongside food, beer, wine, and great music.
  • Back to the Bash Bowl: June 22, 2024 6-10:30pm Wallace Bowl in Gillson Park, Wilmette. The Back the Bowl Bash (formerly Beach Bash) will feature six local bands, cold drinks, dancing, local food, and plenty of FUN!
  • North Shore Artisan Market: June 22 – 23 at Village Green in Northbrook. This curated outdoor market showcases the Midwest’s finest artisans in food, fashion, home goods & art.
  • Art in the Village June 22 and 23, 2024 from 10AM to 5PM at Hubbard Woods Park (939 Green Bay Road) in Winnetka. Art in the Village, a juried art show sponsored by the North Shore Art League will take place at Hubbard Woods Park (939 Green Bay Road) in Winnetka on June 22nd and 23rd, 2024 from 10 am – 5 pm.
  • Off North Shore: Skokie Music Festival: June 21 (4pm) and June 22 (2pm), 2024, outdoors at Skokie Sports Park East. North Shore Center for the Performing Arts in Skokie is excited to announce the first ever Off North Shore: Skokie Music Festival on June 21 & 22, OUTDOORS at Skokie Sports Park East at the corner of Oakton Street and McCormick Boulevard.
  • Highwood Inferno Fest: Wednesday June 26, 2024, 4:30- 9:30 pm, Everts Park | 111 North Ave. Highwood, Illinois 60040. Celebrate Highwood is fired up to bring back Inferno Fest after a seven year hiatus, with spicy food and beverages to test the taste buds of the most fearless food enthusiasts!
  • 18th Annual Bitter Jester Music Festival:
    JUNE 3, 2024: Satellite Series Concert #1 @ Chicago Botanic Gardens
    JUNE 7, 2024: Opening Night Concert
    JUNE 8, 2024: Night Two Concert
    JUNE 10, 2024: Satellite Series Concert #2 @ Chicago Botanic Gardens
    JUNE 14, 2024: Night Three Concert
    JUNE 15, 2024: Night Four Concert
    TBA, 2024: Wild Cards Announced!!
    JUNE 29, 2024: Grand Finale Concert
  • Taste of Highland Park: June 21 and June 22 @5PM to 10PM The Lot (525 Central Ave.).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!
  • Long Grove Strawberry Fest: June 21-23, 2024 @Historic Downtown Long Grove, 145 Old McHenry Road, Long Grove, IL 60047. Sweet summertime fun returns when Strawberry Festival, an annual family tradition, takes over historic downtown Long Grove June 21th through 23rd.
  • Glenview Summer Fest: June 22, 2024 @9AM to 3PM Lehigh Avenue and Jackman Park. The perennial Glenview favorite Summer Fest event takes place Saturday, June 22, bringing in tons of local vendors, crafts, free games, health services, home enhancements, gift ideas, and whole range of delectable foods & beverages for every taste bud.
  • 11th Annual Fun & Fit Family Day at Lambs Farm: June 29, 2024 @9:00 am – 12:00 pm,  Lambs Farm 14245 W Rockland Road, Libertyville, IL. Join us for a fun, family-oriented 5K run or a 2 mile walk to support Lambs Farm on Saturday, June 29 from 9am to 12pm. Registration is now open!
  • Sounds of Summer Bopology: June 23, 2024 @4pm to 5:30pm Mallinckrodt Park. A musical tribute to the Rat-Pack and Swing era, Bopology blends their 50’s and 60’s style for park districts whose residents consist mostly of families and seniors
  • Sounds of Summer Miss Jamies Farm: June 26, 2024 10AM to 11:15AM Mallinckrodt Park. Perfect for pre-schoolers on up through age 8, Miss Jamie and her puppet friends from the farm take the audience on a magical barnyard adventure in a sing-along, dance-along show that’s fun for kids and grownups alike.
  • Sounds of Summer Johnny Russler the Beach Bum Band: June 27, 2024 @7:00PM to 8:30PM, Wallace Bowl.Celebrating the beach, warm summer sun, and island fun, Johnny Russler & The Beach Bum Band are the ultimate party band.
July 2024 Festivals
  • Lincolnshire Art Festival: July 6 and July 7, 2024 @10AM to 5PM, 100 Village Green. Plan your perfect summer day at Lincolnshire’s Village Green! Grab a tasty breakfast with friends or family at your favorite Lincolnshire spot, then browse original art from 80+ artists.
  • Highwood Margarita FestJuly 17, 2024 @4:30 – 9:30PM Everts Park (111 North Ave.). This festive theme night invites attendees to dress in their favorite Jimmy Buffet-style, Parrothead and Hawaiian gear to party to the sounds of a Jimmy Buffet tribute band. There will be beach balls, flamingos, margaritas, Mexican food, key lime pie and more!
  • Highwood Days with Taco Fest: July 18-21, 2024 Everts Park (111 North Ave.).  Recognized as the City’s oldest festival, Highwood Days features one of the area’s largest carnivals, with rides, games, live music and more!
  • Glencoe Festival of Art: July 20 and July 21, 2024 @10AM to 5PM, 700 Vernon Avenue Glencoe, IL, 60022. Get creative at the Glencoe Festival of Art with 100 artists on your perfect summer day with art, food, and fun!
  • Art at the Glen: July 27 and July 28, 2024 @@10AM to 5PM, 2030 Tower Drive Glenview, IL. Come celebrate one of Glenview’s most beloved community traditions! Start your perfect summer day with breakfast at the Glen Town Center, then enjoy thousands of paintings, sculpture, photographs, jewelry and more!
  • Highland Park Sidewalk Sale: July 28 & 29, 2024, 508 Central Avenue, Suite 202 | Highland Park, IL 60035. It’s the event businesses and shoppers have been waiting for! So come out to support and celebrate our community!
  • Northbrook Days Festival: July 31 – Aug 4, 2024, 1401 Shermer Rd. in Northbrook. Every year, volunteers across our community come together for five days and put on an exciting festival for residents of Northbrook and surrounding towns. The fest includes rides, games, live music, food, beer & wine, and much more! It’s been a summer tradition in downtown Northbrook for decades.
August 2024 Festivals
  • Northbrook Days Festival: July 31 – Aug 4, 2024, 1401 Shermer Rd. in Northbrook. Every year, volunteers across our community come together for five days and put on an exciting festival for residents of Northbrook and surrounding towns. The fest includes rides, games, live music, food, beer & wine, and much more! It’s been a summer tradition in downtown Northbrook for decades.
  • Wilmette Art Fair: August 3 and August 4, 2024, @10AM to 5PM, Wilmette & Central Avenues Wilmette, IL, 60091. A perfect summer day awaits at the Wilmette Art Fair! Start your day with breakfast at your favorite downtown Wilmette spot, then enjoy thousands of paintings, sculptures, photographs, jewelry, and more on Wilmette and Central Avenues! Become living art with face painting, and make your masterpiece with a live painting classes.
  • Lake Forest Day 2024: August 6 (6-10PM Carnival) and August 7, 2024 (7AM 5k & Fun Run, 10AM Parade, 11AM-10PM Carnival). The 116th Lake Forest Day celebration is on Tuesday, August 6 and Wednesday, August 7, 2024.
  • Vintage Car Show: August 11, 2024 @12PM to 4PM on St. Johns Avenue. 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!
  • Highwood Garlic Fest: August 14, 2024, @4:30 to 9:30pm Everts Park (111 North Avenue). The smell of garlic brings people from near and far to this festive food-filled fest that showcases a plethora of dishes with the ever-popular taste (and scent) of garlic, with live music and plenty of family-friendly activities to entertain all evening long. Attendees come to sample a variety of sweet and savory garlic creations, from out-of-the-ordinary garlic-infused chocolate, cookies, ice cream, cupcakes, and cocktails, to the classic, savory options like pastas, sandwiches, sauces, and spreads.
  • Evanston Art and Big Fork Festival: August 16 @ 12-5PM and August 17,18 @ 10AM to 5PM, 800 Church St Evanston, IL. The alluring streets of downtown Evanston host the community favorite Evanston Art & Big Fork Festival, August 16-18. Join fellow art lovers in browsing thousands of original pieces from an impressive 150 juried artists showing paintings, sculpture, jewelry, mixed media, photography and so much more.
  • Port Clinton Art Festival: August 24, 25, 2024 @10AM to  5PM, 600 Central Avenue, Highland Park, IL. See paintings, sculpture, mixed media work and more. Get your steps in while browsing thousands of art pieces from 260 of the best artists in the country.
Food Trucks and All Summer Long Festivals
  • Ravinia Food Truck Thursdays: Thursdays, June 6 to September 26, 2024, @4:30 to 6PM, Jens Jensen Park. Mark your calendars: Food Truck Thursdays returns to the Ravinia District this summer June 6 through September 26 at Jens Jensen Park! Savor fresh flavors from a variety of food trucks while enjoying warm summer evenings, and dancing to great music every Thursday night, 4:30 PM to dusk in the Ravinia District! 
  • Highwood Evening Gourmet Market: Wednesdays June 5 to August 28, 2024, @4:30 to 9:30PM, Everts Park. A weekly outdoor market of this caliber is hard to find. With its ‘Live Evening Concert Series’ and ‘Ravinia Festival-like’ atmosphere, Highwood’s Evening Gourmet Market is recognized as one of the best outdoor markets on the North Shore.
  • Wilmette French Market: Saturdays April 20 to November 2, 2024 @8AM to 1PM, just east of the Wilmette Metra Station.  The Wilmette French Market operates every Saturday from 8 a.m. to 1 p.m. just east of the Wilmette Metra Station. The 2024 market runs from April 20 through November 2.
  • Lincolnshire Food Trucks: Thursdays, May 9, 2024 to September 26, 2024 at 11AM to 1:30PM, Lincolnshire Corporate Center Parking Lot: 1 Overlook Point, Lincolnshire, IL 60069.
  • Tuesday Concerts in the Plaza: Tuesdays, June 11 to August 6, 2024 @7PM to 8:30PM, Independence Grove
  • Wednesdays in the Woods Evening ConcertsWednesdays, June 19 to August 28, 2024 @7PM, Hubbard Woods.  Join us for FREE live music every Wednesday night throughout the summer! Bring chairs + blankets to enjoy the warm summer night with friends and family!
  • Wednesdays in the Woods Children’s Concerts: Wednesdays, June 19 to August 7, 2024 @11AM to 11:45AM, Hubbard Woods. Join us for free interactive children’s concerts! Bring a picnic lunch or pick up food from one of the nearby Hubbard Woods businesses.
  • Music on the Esplanade at Chicago Botanic Garden: June to August 2024 @at Chicago Botanic Garden, see event link for different schedules.
  • Downtown Evanston’s Thursday Night Market: June 6, July 11, August 1, and September 5, from 4:30-7:30PM at Fountain Square. Now entering its 5th year, Downtown Evanston’s Thursday Night Markets showcase artists, makers, and retailers from the local community. Each market will feature 30+ vendors, a DJ or live music, and other special activities.
  • Fueled Coffee and Classics: May 26, June 30, July 28, August 25, September 29, October 27 @9AM to 11AM, At Elm & Lincoln Ave. in downtown Winnetka. Please enjoy the cars and feel free to talk to owners. We love sharing our passion with others. The cars are also investments that can be damaged more easily than you might think.
Farmers Markets

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