The North Shore of Chicago is filled with vibrant communities and years-long traditions that usher in excitement each summer. With endless possibilities — such as outdoor live music, a scenic 5k race, art in the park, and more — everyone is welcome to join in the fun. Read on for a selection of the best summer events on Chicago’s North Shore.
Tag us in your summer adventures on Instagram @makeitbetter_foundation — we’d love to see where the month takes you.
June 20-21: Winnetka Music Festival
The 2025 Winnetka Music Festival will be held this June in Downtown Winnetka. Visitors can expect two days of live music across four stages, free family programming, plenty of delicious food options; a dedicated wine bar and an array of tasty beverages; interviews and performances; and so much more! Visit Winnetka Music Festival online for more details
June 21-22: North Shore Artisan Market
The North Shore Artisan Market — one of a few locations in Chicagoland — celebrates the ingenuity of independently owned, small businesses who channel their passions into creating one-of-a-kind products. Meet & shop with the artisans themselves. Shop small and support local. More information can be found on the North Shore Artisan Market website.
June 21: Glenview Summer Fest
Glenview Summer Fest is bringing together tons of local vendors, crafts, free games, health services, home enhancements, gift ideas, and a variety of delectable foods & beverages for everyone to enjoy. This event is held on two village blocks of Lehigh, from Glenview Road to Washington. The fest goes on rain or shine, so visit Glenview Summer Fest website for all the info you need.
June 28: Run the Runway, Wheeling
Head over to the Chicago Executive Airport for Run the Runway, Wheeling. This event is more than just a race, however. The morning kicks off with a guided stretch, then the 5k and 1 mile kick off, followed by the Kids Dash and awards ceremony. Stick around for sponsor giveaways, special guest appearances by Elsa and Spiderman, kids activities, prize drawings, music and more. Details on the Run the Runway, Wheeling site.
June 28: Main Street—Evanston
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Come celebrate the summer in downtown Evanston with the Main Street market, from 11am-9pm. Enjoy the 90+ booths of artist and vendors, 3 stages of Fantastic Local Musil, jazz brunch, and kids activities. Visit the Main Street—Evanston for all details on the event.
July 16-20: Evanston Plein Air Festival
The 4th Annual Plein Air Festival is a citywide summer arts festival inviting the community to join in the joy. Artists are invited to paint in the Plein Air style, all over Evanston, capturing the beauty of Evanston’s natural environment, favorite landmarks and built environment.
July 19-20: Glencoe Festival of Art
The Glencoe Festival of Art will feature 100 artists, plus food and fun! Enjoy thousands of paintings, sculptures, photography, jewelry, and more. Stop at the Kids Art Zone for more art projects, face painting, and bubbles. For adults, hang around for the live music, cold beverages, and a variety of vendors. Details on the Glencoe Festival of Art.
July 24-27: Lincolnwood Fest
Community members love this fest every year! The Lincolnwood Fest is all about family and friends coming together for classic festival fun. The fest features daily live music from local and regional acts, a business expo, carnival rides, games, bingo, a Classic Car Show and so much more! For additional information for this year’s Lincolnwood Fest, visit them online.
July 24: Northbrook Grand Prix
Whether you’re new to this or a pro, The Northbrook Grand Prix welcomes all who are excited about biking. There will be a Community Ride for everyone, followed by the final Northbrook Grand Prix races for professionals. However, bikes are not required to enjoy all the outdoor activities that the Northbrook Park District has planned for non-riders. Find all the information you need at Northbrook Grand Prix.
July 26-27: Art at the Glen Town Center
This art fest is one of Glenview’s most beloved community traditions. Enjoy the work of over 130 artists, from paintings, sculpture, photographs, jewelry and more while you visit. There will also be face painting and a live painting classes. Don’t forget to check out the live music and delicious local food. There’s something for everyone from traditional to modern tastes. Check out Art at the Glen Town Center to see all they have lined up.
August 2-3: Wilmette Art Fair
At the Wilmette Art Fair, it is about more than just the art. Though you can’t forget that either, with 100 artists in attendance from paintings to sculptures, and photographs to jewelry. For the kids, there will be a Kid Friendly Art Tent, and for the adults there are cold beverages and live music ready to rock. Bring the whole family, and check out Wilmette Art Fair online to know before you go.
August 16-17: Evanston Art and Big Fork Festival
This August, join fellow art lovers in browsing thousands of original pieces from 150 juried artists showing paintings, sculpture, jewelry, mixed media, photography and more. Take a break at the delicious foods area, try a painting class, have a personalized poem written for you, or visit the Kids Art Zone with your kiddos. All of this fun awaits in Evanston, check out the Evanston Art and Big Fork Festival for more.
August 22-24: Skokie’s Backlot Bash
The Backlot Bash knows how to keep people entertained and happy! That’s why their idea of a good time includes live music, carnival rides, great food and beer, a 5k, community pancake breakfast, and so much more. Check out the Skokie’s Backlot Bash online to learn more about this annual tradition.
September 6-7: Evanston Folk Festival
Returning for a second year, the Evanston Folk Festival celebrates beautiful music and community right on the shores of Dawes Park on Chicago’s North Shore. Enjoy the music of over 30 world-class artists with Lake Michigan as the backdrop. There will also be in-person interviews and panels with authors and luminaries presented by Chicago Public Media. Each day is packed with good fun for everyone, visit the Evanston Folk Festival for details.
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Margaret Smith is a Chicago-based writer and editor with a passion for socio-political storytelling about their community. They are a graduate of Columbia College Chicago.
