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Winter Street in Downtown Kankakee
Downtown Kankakee Events - Merchant Street Music Festival logo

Winter Market

Your favorite local vendors, now in the winter!

Beautiful Downtown Kankakee during the day
Downtown Kankakee Events - Merchant Street Music Festival logo

Downtown Kankakee

Livable, Walkable, Workable
Welcome to the historic Downtown Kankakee District!

Downtown Kankakee Events - Merchant Street Music Festival logo

Sunset Stroll

Bi-Annual Street Fest On North & South Schuyler
Sunset Stroll North - May & Sunset Stroll South - Aug

See you in May & August
Downtown Kankakee Events - Merchant Street Music Festival logo

Merchant Street MusicFest

Love. Peace + Good Vibes.
Annual two-day music and arts festival in Downtown Kankakee

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WELCOME to downtown kankakee

Downtown Kankakee offers a vibrant mix of commerce, culture, and community. From farmers markets and street festivals to live music, car shows, and seasonal celebrations, Downtown Kankakee continues to attract new businesses along with unique food and drink experiences for residents and visitors alike.
 

Below are signature events happening in Downtown Kankakee showcasing the energy and community spirit that's been helping make the experience of our historic town so special over the years. Click a local happening below to learn more!

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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

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.

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.

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.

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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. 

THE DEPOT

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:

The Depot Railroad station in downtown kankakee

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

News & Development in Downtown Kankakee

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Businesses

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February 27, 2026

Resilient Comfort Care - Black History Month Q&A

In this featured Q&A, we spotlight Resilient Comfort Care, a Black-owned home care agency in Downtown Kankakee. From personal experience caring for a loved one to building a trusted business that supports seniors and families, this story highlights compassion, perseverance, and the meaningful impact of serving your community.

Businesses

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February 26, 2026

The Venu’ - Black History Month Q&A

In this featured Q&A, we spotlight The Venu’ Lounge and V2 Event Space and the vision behind creating two dynamic gathering spaces in Downtown Kankakee. From live jazz and crafted cocktails to intimate celebrations and community events, this story highlights perseverance, purpose, and the power of investing in your own dream.

Businesses

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February 24, 2026

906 Clothing - Black History Month Q&A

In this featured Q&A, we highlight a local Black-owned business - 906 Clothing - in Downtown Kankakee and share the story behind the owner’s journey. From how the business began to the challenges, inspiration, and impact within the community, this conversation celebrates entrepreneurship, representation, and the power of building legacy close to home.

Community

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February 23, 2026

Building An Archive: Preserving Kankakee's Black Business History

Downtown Kankakee is where our community, culture, and history meet. It's a place where all are welcome to gather and celebrate all the vibrancy of our city. As we continue telling the story of our city's downtown heritage, we've recognized an important gap: much of the history of Black entrepreneurship in Kankakee has never been formally documented or preserved.

This Black History Month, we're launching a community archive project to change that.

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