Fall is in full swing, and St. Louis is buzzing with events you don’t want to miss! Whether you’re in the mood for live music, cultural festivals, family fun, or foodie adventures, the city is serving up something for everyone. From hidden gems to can’t-miss celebrations, here’s your guide for the best weekend in St. Louis, September 26–28.

Live Music

Get ready to party with one of St. Louis’s premier bands, Dirty Muggs, as they hit the stage at Trainwreck Saloon Westport on Thursday, September 26 at 8:30 PM! Known for their explosive energy, electrifying mashups, and crowd-rocking performances, Dirty Muggs always deliver a show that keeps the dance floor packed and the vibes high. It’s a guaranteed fun time.

Get ready for an unforgettable night of music when Trombone Shorty & Orleans Avenue bring their high-energy blend of funk, jazz, R&B, and soul to The Pageant on Thursday, September 26 at 7:00 PM. Known for his electrifying stage presence and genre-bending sound, Trombone Shorty has become a New Orleans legend, captivating audiences around the world with his signature horn and powerhouse performances.

Joining him is rising singer-songwriter Abraham Alexander, whose soulful voice and heartfelt lyrics have been earning national acclaim. Together, they promise an evening filled with rhythm, passion, and the spirit of New Orleans right here in St. Louis.

Groove to the smooth, sultry sounds of Sade at the National Blues Museum’s “Smooth Operator”, a special Soulful Sunday tribute to one of music’s most timeless and beloved artists. Sunday, September 28 at 5:00 PM.

Local Festivals

Enjoy a vibrant evening of smooth sounds and soulful rhythms at the Clayton Jazz Festival, happening on Saturday, September 27 from 5:00–10:00 PM at Carondelet Plaza in Downtown Clayton. This free outdoor festival brings together some of St. Louis’ finest jazz talent along with nationally renowned musicians for an unforgettable night of live music.

Celebrate love, unity, and community at Tower Grove Pride Fest, one of St. Louis’s most vibrant and inclusive events of the year! Held in the beautiful Tower Grove Park, this free festival brings together thousands of people for a joyful weekend filled with live music, local vendors, food trucks, and family-friendly fun. Admission to the festival is FREE. Sept 27; 11AM-6PM Sept 27; 11AM-5PM

Arts, Culture, Theatre

Art in the Park returns to Francis Park on September 28, 2025. This beloved community event transforms the park into an open-air gallery, featuring works from talented local and regional artists across a variety of mediums.

Experience theater like never before with Shakespeare in the Streets, a powerful new production written by DeAsia Paige and directed by Kathryn Bentley. Presented at the House of Miles in East St. Louis from September 25–27, 2025, this world-premiere play reimagines the timeless themes of Shakespeare through the lens of the historic “City of Champions.”

Blending community voices, local history, and the artistry of live performance, Shakespeare in the Streets transforms everyday stories into extraordinary theater. Audiences can expect an unforgettable evening that honors East St. Louis’s resilience, culture, and spirit while shining a light on the people who continue to shape its legacy.

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