Festivals on Chicago’s North Shore 2026

Highwood Evening Gourmet Market: Wednesdays, June 3 – Aug 26, 2026 at 4:30 pm – 9:00 pm. Celebrate Highwood is thrilled to announce its 2026 Wednesday Evening Gourmet Market music line-up at the bandshell in Everts Park (111 North Avenue, Highwood)! A highly coveted destination on the North Shore for Wednesday evening gigs, the weekly outdoor music series offers the community free live entertainment.

Kick-Off to Summer Carnival: Friday, June 5 – Sunday, June 7, 2026, Downtown Highwood Metra Station Parking Lot. The community is invited to come out and mark the beginning of summer at this festive carnival with rides, games, and food. Families are invited to celebrate with discounted unlimited ride wristbands.

Art in the Village: June 13 and June 14 from 10 am – 5  pm, in Hubbard Woods  Park, Green Bay Road, Winnetka. NSAL, sponsored by the North Shore Art League. Celebrating over 100 years of art in the community, is proud to promote this annual  juried show. The park is a beautiful setting for a summer art fair – in the middle of the Village’s

Blues Beats – Concert for Kids: June 13 and June 20 from 10:30 am – 12:30  pm, Woman’s Club of Wilmette, 930 Greenleaf Ave, Wilmette, Illinois 60091. Families are invited to learn and celebrate the Summer with Family Blues and Pop Music and Grammy-nominated Wendy and DB. Originally Blues and Pop Songs about Nature, Self-worth, Community, and Love!

Pride in the Park: Friday, Wednesday June 17, 2026 at 4:30- 9:00 pm, Everts Park.

Taste of Highland Park: Friday, June 19 | 5 PM – 10 PM, Saturday, June 20 | 3 PM – 10 PM, Port Clinton Square | 600 Central Ave. Highland Park’s premiere food and music festival returns in 2026 with more music, more food, and more fun! Savor the taste of summer with delicious dishes and select beverages specially curated from over one dozen local Highland Park restaurants, all while jamming out to exceptional live entertainment. Get a taste of what sets Highland Park’s restaurant scene apart on Chicago’s North Shore

Winnetka Music Festival: June 19 and 20, Downtown Winnetka. Established in 2017, Winnetka Music Festival is a homegrown summer concert series taking place in Downtown Winnetka, Illinois on Chicago’s beautiful North Shore. 

Inferno Fest: Wednesday June 24, 2026 at 4:30 – 9:00 pm, Everts Park. Celebrate Highwood is fired up to bring you summer’s hottest event, Inferno Fest, with spicy food and beverages to test the taste buds of the most fearless food enthusiasts!

Evanston Main Street Fair: Saturday, June 27, 2026 at 11:00 am – 9:00 pm, Main Street & Chicago Ave. in Evanston. Main Street Fair is an annual outdoor festival featuring live music on three stages, performers like our very own School of Rock Evanston and School of Rock Highwood, food, artists, makers, family-friendly activities, and more!

Lake County Greek Fest: July 10, 11, 12 @ 11:00 am – 9:00 pm, St. Demetrios Greek Orthodox Church. Join us for one of Lake County’s favorite summer traditions at St. Demetrios Greek Orthodox Church in Libertyville! Enjoy a weekend filled with authentic Greek food, homemade pastries, live music, family fun, and warm Greek hospitality.

Summer Bash: July 11 @ 12:00 pm – 8:00 pm, Meyer Sports Complex 2065 Half Day Rd., Bannockburn. Get ready for one of the North Shore’s newest summer bash! Hosted by the Donato Foundation, Summer Bash features live entertainment from Sparks Fly: The Taylor Swift Experience, 90s Pop Nation and Whiskey Friends: The Morgan Wallen Experience, plus food trucks, inflatables, family activities, local vendors and community fun for all ages. Proceeds support youth athletes and families throughout our community. Use code BASH26 for $10 off four or more tickets.

Highwood Days Carnival: Friday, July 17 – Sunday, July 19, 2026, Downtown Highwood Metra Station Parking Lot. Recognized as the City’s oldest festival, Highwood Days features one of the area’s most popular carnivals, with rides, games, live music and more! The addition of the Taste of Highwood brings together the City’s numerous restaurants and specialty food operations to offer a wide range of mouth-watering creations, along with full booze tents. Attendees will enjoy casting their vote for the People’s Choice Award for the Best Taste of Highwood.

Taste of Highwood (2nd Annual): Friday July 17 – Sunday July 19, 2026, Everts Park. Recognized as the City’s oldest festival, Highwood Days features one of the area’s most popular carnivals, with rides, games, live music and more! The addition of the Taste of Highwood brings together the City’s numerous restaurants and specialty food operations to offer a wide range of mouth-watering creations, along with full booze tents. Attendees will enjoy casting their vote for the People’s Choice Award for the Best Taste of Highwood.

Highwood 5K Run, Walk & Stroll: Saturday, July 18, 2026 9 am, Downtown Highwood. Recognized as the City’s oldest festival, Highwood Days features one of the area’s most popular carnivals, with rides, games, live music and more! The addition of the Taste of Highwood brings together the City’s numerous restaurants and specialty food operations to offer a wide range of mouth-watering creations, along with full booze tents. Attendees will enjoy casting their vote for the People’s Choice Award for the Best Taste of Highwood.

Margarita Night: Wednesday, July 29, 2026 at 4:30 – 9:00 pm, Everts Park. 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, Carribean food, key lime pie and more!

Downtown Concerts at Port Clinton: Fridays, July 10 – September 25, Port Clinton Square | 600 Central Ave. Spend your Friday evenings at Port Clinton with great food and great music. Enjoy 10 Friday evening concerts featuring performances from a variety of artists and genres (including special performances by Highland Park performing arts groups) and on-site food and beverage vendors. The extended finale concert will take place September 25 (from 4 PM – 8 PM) and will feature the return of the ever-popular Scarecrow Trail.

Garlic Fest: Wednesday, August 12, 2026 at 4:30 – 9:00 pm, Everts Park. 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. The Fest features a Taste of Garlic Competition for the best Savory and Sweet creations and the innovative dishes never disappoint!

Bloody Mary Fest: Sunday, August 16, 2026 at 10 am – 5 -pm, Everts Park. Recognized as the City’s oldest festival, Highwood Days features one of the area’s most popular carnivals, with rides, games, live music and more! The addition of the Taste of Highwood brings together the City’s numerous restaurants and specialty food operations to offer a wide range of mouth-watering creations, along with full booze tents. Attendees will enjoy casting their vote for the People’s Choice Award for the Best Taste of Highwood.

Vintage Car Show: Saturday, August 22 | 12 PM – 4 PM, St. Johns North Lot | 525 Central Ave. Step back in time and experience the elegance, craftsmanship, and the nostalgia of a bygone era. Relive the golden age of automobiles at the Vintage Car Show on Saturday, August 22. Head to the St. John’s North Lot (525 Central Ave.) and peruse a fabulous array of over 200 vintage, classic, and antique vehicles, hot rods, muscle cars, and pop culture icons all while enjoying a live radio broadcast, kid-friendly activities, delicious food, and ice cold beverages.

Nashwood: Labor Day Weekend, September 4 – September 6, 2026, Downtown Highwood. Watch Highwood transform into Nashville over Labor Day weekend. Highwood restaurants and bars will feature 100 free, live country, southern blues, classic and contemporary rock from beginning Friday happy hour and running all day and evening Saturday and Sunday.

Oktoberfest: Saturday, September 26 | 4 PM – 8 PM, Jens Jensen Park | 540 Roger Williams Ave. Back by popular demand! Oktoberfest returns as a City-produced event in 2026. Enjoy classic Oktoberfest fare, entertainment, a bier hall, and games (like axe throwing, a high striker, and hammerschlagen), plus special children’s programming.

The Great Highwood Pumpkin Fest:
Thursday, October 1 – Community Night & Opening Carnival
Friday, October 2 – Sunday, October 4. 2026
The Great Highwood Pumpkin Festival is the biggest outdoor celebration on Chicago’s North Shore featuring all-you-can-carve pumpkins, nightly lightings of pumpkin-filled walls, carnival rides, costume and pumpkin pie eating contests, trick or treating, two stages with live music, seasonal interactive installations, food and beverage vendors and so much more!

Stews & Brews: Saturday, October 10 | 4 PM – 9 PM, Port Clinton Square | 600 Central Ave. Stews & Brews returns to Downtown Highland Park for a fifth season! This HP-exclusive event combines two Midwestern favorites: comfort foods and beverages. Stay cozy with fire pits, heaters, hearty food, and great live music. The evening culminates with a People’s Choice competition for the favorite Stew and Brew. This event is sure to warm the hearts and souls of all who attend!

Elf Invasion Pub Crawl: Saturday, December 5, 2026, 2 PM-Bar Close. Calling all elves to come out and get “Elfed Up’ at the Annual “Elf Invasion Pub Crawl.” The public is invited to channel their inner elf, dress the part, and join a troupe of elves as they visit the City of Highwood’s most popular establishments to enjoy live music, food and drink specials, and raffle prizes.

We got your food trucks, farmer’s markets and other summer markets right here!