Get ready for an unforgettable musical journey as The Windy City Ramblers and Fletcher Rockwell bring the energy to First Fridays: Chicago-Austin!

The Windy City Ramblers Brass Band is a powerhouse nonprofit ensemble rooted in the spirit of New Orleans second line traditions and infused with Chicago soul. Dedicated to uplifting youth through cultural education and musical excellence, their performances are a vibrant mix of tradition, rhythm, and celebration. Expect brass-driven grooves that move your feet and stir your spirit.

Then, shift gears with Fletcher Rockwell, Chicago’s own Americana rock outfit known for their heartfelt originals and crowd-pleasing covers. With sounds that blend blue-collar grit and Nashville twang, they deliver a rich set that spans Tom Petty to Chris Stapleton—equal parts rootsy, nostalgic, and bold. Whether you’re in the mood to dance, sing along, or sway to the soulful tones of “Tennessee Whiskey,” this band’s got you covered.

Together, they bring the best of brass and rock—New Orleans spirit meets Midwestern heart.

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 Chicago-Austin district 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 Chicago-Austin district below—and visit PickOakPark.com for a deeper dive into all the incredible businesses that call this corridor home.