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Festivals, Markets & Downtown Fun All Year Long

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Things to Do in Downtown Kankakee

There’s always something happening in Downtown Kankakee. From live music and outdoor festivals to community gatherings and seasonal celebrations. Explore upcoming Kankakee events and discover new ways to enjoy the heart of the city with friends, family, and neighbors.
 

Whether you’re planning a night out, searching for fun things to do in Kankakee, or keeping track of your favorite annual events, this page brings everything together in one place. Don’t miss signature experiences like the Kankakee Farmers Market, Sunset Stroll on Schuyler,  Merchant Street Music Festival and more events happening throughout the year.

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Kankakee Winter Market Logo
Kankakee Sunset Stroll on North Schuyler
Merchant Street Music Festival logo
Kankakee Sunset Stroll on South Schuyler
Sandwiches with a side of Jam logo
Friday Night Concert Series logo
Kankakee Farmers Market logo
Cruis'n the Square logo
Coffee Cars and Cigars logo
Ariel view of historic downtown kankakee

Upcoming Events in Downtown Kankakee

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Mar 14th, 2026

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Winter Market

Ringing in 2026 with something new! Warm up at the Downtown Kankakee pilot "Winter Market" at The Majestic starting Saturday, Jan 24th and again on Saturday Feb 21 & Mar 14

Friday | May 29 | 2026

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Sunset Stroll North

Beautiful night of fun, music, friendship and a region coming together. Celebrating the businesses of the 1st ward and the people of our community.

July 24 & 25, 2026

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Merchant Street Music Fest

Two unforgettable days of live music, local flavor, and community energy. Celebrating the heart of Merchant Street and the people who make Kankakee shine.

June - August

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Friday Night Concert Series

Kick off your weekend with the Friday Night Concert Series in Downtown Kankakee, featuring live music, open air vibes, and a lively crowd. Bring a chair, relax on the Square, and enjoy a night of great sound and community.

June - August

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Sandwiches with a side of Jam

Enjoy Sandwiches with a Side of Jam at Festival Square featuring lunchtime sandwiches, live music, and laid-back vibes by the Kankakee depot.

Friday | Aug 21 | 2026

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Sunset Stroll South

A lively street festival of food, music, and community under the summer sky. Celebrating the businesses of the south end of downtown and the people who keep it moving forward.

Multiple Dates

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Coffee, Cars & Cigars

Kick off your morning with classic cars, good coffee, and smooth cigars. Stroll through a lineup of cool rides, chat with fellow enthusiasts, and enjoy some great music and easy vibes.

May - October

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Cruisn' The Square

Cruise into Downtown Kankakee for a car show on the Square featuring classic cars, custom builds, and hometown pride. Stroll the Square, meet fellow car lovers, and enjoy a day of chrome, engines, and community.

May - October

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Farmers' Market

Visit the Kankakee Farmers Market in Downtown Kankakee, IL. Saturdays May–October, 8 AM–12 PM. Fresh local produce, food vendors, handmade goods, live music & community fun.

Annual Events Map

Discover Downtown Kankakee’s biggest events. Click the map markers to explore festival locations, concerts, and more.

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Harold and Jean Minor Festival Square fountain

Harold & Jean Miner Festival Square

HAROLD & JEAN MINER FESTIVAL SQUARE

Quick look: Festival Square is basically the centerpiece of Downtown Kankakee and the general location for many of its events. 

At the heart of Downtown is the Harold & Jean Miner Festival Square, framed by Kankakee’s 120+ year-old Depot behind it. Festival Square has become the stage for many of the community’s biggest moments. Each summer, Merchant Street MusicFest fills the district with live music and art that draws thousands of people downtown. From concerts and festivals to everyday gatherings, this is where Kankakee’s history and its future come together, always in motion just like the trains that continue to pass through. 

Flower mural in downtownkankakee
Finding Frank Mural in downtown kankakee
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Hub Mural in downtown kankakee

MURALS OF DOWNTOWN KANKAKEE

Quick look:  We have amazing muralists and local artists here in Kankakee. You should check them alllllll out. Event the ones not "officially" in the KDC District.

Downtown Kankakee is alive with color, thanks to the incredible talent of artists who have transformed blank walls into vibrant works of art. From bold geometric patterns inspired by Frank Lloyd Wright to the bright blossoms of our native flowers, each mural tells a story about the people, the history, and the creativity that define our community. These works are not hidden away in galleries. They are right here on the streets, waiting to be admired on a casual walk or captured in a photo.

Local artists and community partners have come together to create pieces that celebrate Kankakee’s past while reflecting the spirit of today. Whether you are discovering them for the first time or revisiting old favorites, the murals of Downtown Kankakee make the district itself a living, evolving canvas.

The railroad Depot old postcard in downtown kankakee

The Depot - Kankakee IL (1910) Postcard from A.C. Bosselman & Co.

THE DEPOT - ILLINOIS CENTRAL LINE

Quick look: Kankakee literally wouldn't  be on the map without this railroad station. It was built in 1853 and upgraded to the brick building that still stands today since 1898. 

Kankakee owes its very existence to the railroad. When the Illinois Central line reached the banks of the Kankakee River in 1853, the first wood-framed Depot was built on July 11th, 1853 as a stop along the route. That single decision put Kankakee on the map, drawing settlers, businesses, and industry to what was once open prairie. The town quickly grew around the station, and by 1854 it was officially incorporated as a city. The building was upgraded from wood to brick in 1898 and more than 120+ years later, the brick Depot is still in operation and stands as a reminder that without the trains, there would be no Kankakee. From The Depot,  you can head north to Chicago’s Union Station or south toward cities like Champaign and Carbondale.  It also houses the Kankakee Railroad Museum!

We're sorry, The Depot is currently no longer available to rent for private events. Allow us to suggest a nearby Downtown Kankakee venues below:

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