Experience the heartbeat of Pleasant District with a night full of live music and celebration.

The Very Least (5:00-5:45)

Blending indie, soul, funk, and pop into groove-heavy originals full of warmth and heart. With tight rhythms and infectious energy, their music is as danceable as it is emotionally rich.

Greenlights (6:15–7:00 PM)

A six-emcee hip hop collective backed by a powerhouse live band. Mixing sharp lyricism with soulful instrumentation, they deliver uplifting, high-energy performances that have twice earned them “Best Hip Hop Group” honors from the Chicago Reader

ESSO (7:30–9:00 PM)

Lighting up the stage with a vibrant fusion of Latin funk, jazz, slam poetry, and rock. Their groove-driven sound transforms the dance floor into a global celebration, earning them recognition on international stages and beyond.

Bring the whole crew to the Family Fun Zone—packed with activities for kids (and kids at heart)! Climb, race, and bounce your way through the inflatable obstacle course, get your face painted, create something magical at the craft table, and pop bubbles in the sunshine. Test your skills with classic carnival games like Pop-A-Shot, Plinko, Fish Pond, and more. From high-energy fun to hands-on creativity, there’s something for everyone to enjoy!

Fuel up while you enjoy the festivities! Our festival bar will be pouring Bud Light, Goose Island 312, Cutwater Cocktails, and non-alcoholic options to keep you cool and refreshed.

Plus, local restaurants in the Madison will be open and serving up their neighborhood favorites—so be sure to stop in and show them some love! You’ll also find a few special food vendors set up along the street, offering tasty bites perfect for snacking as you stroll, dance, or play.

There’s something delicious for everyone—come hungry!

Stroll the street and discover a dynamic mix of local businesses, artists, and community organizations bringing their best to First Fridays! From handmade goods to local services and unique finds, there’s plenty to explore and enjoy.

Check out the full list of vendors for the Madison district below—and visit PickOakPark.com for a deeper dive into all the incredible businesses that call this corridor home.