Sunset Stroll - Downtown Kankakee

Twice a Year | North & South Schuyler Streetscapes
Free Community Event | All Ages Welcome
6:00PM - 9:00PM

Celebrate the changing seasons and the vibrant spirit of Downtown Kankakee at our Sunset Stroll – a free, family-friendly street festival that takes place twice a year, once to kick off summer and again to send it off in style.

Each Sunset Stroll transforms Schuyler Avenue into a lively pedestrian experience, filled with live music, delicious local eats, open-air drinks, and entertainment for all ages.

2025 Sunset Strolls:

May 30th (North Schuyler)
Mothpoint + Southside Social Club
Food: Martinez Tacos + Mia Bella

Aug 22nd (South Schuyler)
Three's a Crowd + Windy City Ramblers
Food: Martinez Tacos + Brother George's BBQ

What to Expect:

SLOW ROLL community bike rides kicking off at 6:00 PM
Live Music from talented local bands starting at 6:30 PM
Street Performers including fire-twirlers and stilt walkers by Intrinsic Arts
Outdoor Dining and food vendors from your favorite Downtown eateries
Open Container District – adults 21+ can stroll with purchased beverages (wristband required)
Shopping & Specials at Downtown businesses, many offering extended hours
Family-Friendly Fun all evening long!

Whether you're joining us in the North Schuyler Streetscape near the historic Majestic Theatre, or along the South Schuyler Streetscape near the Gazebo, each Sunset Stroll has its own unique flavor and lineup — but always promises good vibes, good food, and a great time.

Grab your friends, your bike, and your favorite walking shoes – Sunset Stroll is your invitation to unwind, explore, and enjoy everything Downtown Kankakee has to offer.