Square Roots Festival Returns Featuring Calexico, Ted Leo & The Pharmacists, and Alejandro Escovedo

This year’s lineup showcases an exciting mix of talent from Chicago and around the world, including standout acts like The Lone Bellow, Heartless Bastards, Mekons, Verböten, Big Sandy & His Fly-Rite Boys, Cesar Rosas & The Chi-Town Playboys, and many more.

Lincoln Square is gearing up for its annual rite of summer—the return of the Square Roots Festival next month. It’s a three-day celebration that promises to turn Lincoln Avenue between Montrose and Wilson into a vibrant, music-fueled block party, complete with craft beer, food trucks, and enough family-friendly activities to keep the kids busy while the adults soak it all in.

Organized by the Lincoln Square Ravenswood Chamber of Commerce and the Old Town School of Folk Music, Square Roots isn’t just another street festival. It’s the neighborhood’s way of reminding itself—and the city - that this corner of Chicago has its own pulse, its own soundtrack. The lineup this year reads like a love letter to both local grit and international flair: headliners like Calexico and Alejandro Escovedo share the bill with Chicago staples like Ted Leo & The Pharmacists and The Lone Bellow, while the Cosmic Country Showcase and Big Sandy & His Fly-Rite Boys add a touch of the unexpected.

But the music is just the headline act. Food vendors like Bad Johnny’s are firing up wood-fired pizzas, while Avrom Farm brings the fajitas. Local breweries such as Dovetail and Half Acre pour craft beer that’s as much a part of the neighborhood’s identity as the music. And for families, the Sunnyside Kids Zone returns with performances by the Old Town School’s Wiggleworms and the Cooper Mariachi Ensemble, ensuring the festival is as much about community as it is about entertainment.

Square Roots is a reminder that festivals like this are about more than just good times. They’re about sustaining the local ecosystem—supporting nonprofits, nurturing artists, and keeping the spirit of Lincoln Square alive. The proceeds benefit the Chamber of Commerce and the Old Town School, two institutions that have long been the backbone of this neighborhood’s cultural life.

In a city that’s always chasing the next big thing, Square Roots feels like a necessary pause - a chance to celebrate what’s been built here, block by block, note by note. It’s a festival that wears its heart on its sleeve, inviting everyone to come out, listen, eat, and remember why Lincoln Square still matters.

For the full lineup and vendor details, the official Square Roots website and social channels have you covered. But if you ask me, the real draw is the feeling you get walking down Lincoln Avenue during those three days - the hum of a neighborhood that’s alive, kicking, and ready to root itself even deeper into Chicago’s summer soundtrack.