Things to Do in Winona, MN
in September 2026
The bluffs are turning, the river air is crisp, and September brings some of the best events of the year to Winona’s riverbanks, stages, and gathering places.
September is the sweet spot on Winona’s calendar. The humidity breaks, the limestone bluffs above the Mississippi start pulling on their fall colors, and the community fills its weeks with live music, local storytelling, collector culture, and riverfront celebrations you won’t find anywhere else in the region. Here’s what’s on for September 2026.
Winona Jazz Collective Performance
Live jazz improvisation from the local collective, hosted through the Upper Mississippi Jazz Society. An intimate evening of spontaneous, locally-rooted jazz at one of Winona’s most beloved neighborhood bars.
Event Details →Makerspace Open Tour
A free public walk-through of the woodshop, metal shop, and print labs at the Winona Creators Collective. Whether you’re a seasoned maker or just curious about what’s being built in the community, this tour is open to everyone.
Event Details →Karate Camp 3 Music Festival
Over a dozen independent bands, camping, and wood-fired pizza across two days at Briggs Outdoors. Karate Camp is one of the Driftless region’s favorite underground music experiences — DIY, community-run, and well worth the drive.
Event Details →PEZ on the River Convention
The 13th annual PEZ collector’s toy show and costume contest returns to Winona. Whether you’re a lifelong PEZ hunter or just here for the spectacle, this quirky and beloved event delivers on both counts.
Event Details →Business & Immigrant Stories of Winona
Live local narratives presented by Project FINE and the Sandbar Storytelling Festival. Real stories from Winona’s business owners and immigrant community members, told in their own words at the History Center.
Event Details →Comedy Night with Chris Maddock
Live stand-up comedy inside the ballroom at the Winona Athletic Club. A rare chance to catch a quality live standup performance right in town — bring friends and plan to stay a while.
Event Details →HWY 61 Concert Series: Billy Joel Tribute
Mick Sterling performs Billy Joel’s classic albums “The Stranger” and “An Innocent Man” in full. Part of the acclaimed HWY 61 Concert Series — a polished, high-energy tribute in one of Winona’s finest performance venues.
Event Details →Boats and Bluegrass Festival
National roots and string-band acts perform right on the riverbanks at Prairie Island Park across a full September weekend. Peak bluff-country foliage, live bluegrass, and the Mississippi River as your backdrop — it doesn’t get more Winona than this.
Event Details →360
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