As the air turns crisper and the leaves blaze in gold, orange, and red, Winona comes alive with festivities that celebrate autumn’s best. From music and storytelling to heritage and community fun, there’s something for everyone. If you’re looking for weekend plans or ways to make the most of fall in Bluff Country, here are several annual events in and around Winona you won’t want to miss.
Boats & Bluegrass Festival
When: September 25th-28th
What: A beloved music festival blending bluegrass, folk, and Americana against the backdrop of the Mississippi River. There’s camping involved, multiple stages, and a river-campground setting that makes this more than just a concert — it’s a full escape.
Sandbar Storytelling Festival
When: October 7th-11th
What: Unique among fall offerings, the Sandbar Festival honors the art of story, live performances, workshops, food, concerts, and more at Saint Mary’s University. It’s perfect for those who love culture, folk narratives, and sitting around fires with tales.
Polish Smaczne Jablka (Apple Day)
When: October 5th
What: A celebration of Winona’s Polish (particularly Kashubian) heritage, Apple Day (Smaczne Jablka) brings together food, music, apple-themed treats, art, and community tradition. If you love food, folk tradition, or just good local atmosphere, this one’s a fall must.
Voices of the Past Cemetery Walk
When: October 4th and 5th
What: History comes alive at Woodlawn Cemetery as local actors portray Winona’s past in thematic presentations. It’s spooky in the best way: reflective, educational, and a beautiful way to see fall shades while connecting with local heritage.
St. John Nepomucene Parish Annual Fall Festival
When: October 20 from 11 a.m. to 3 p.m.
What: Lunch, big ticket drawing, quilt and cash raffle, silent auction, gift-card raffles, and sweet treats like a cupcake walk. Great for families and getting to know neighbors.
Tips for Festival-Goers
- Check the dates ahead of time. Fall events tend to shift from year to year, especially church festivals and smaller gatherings.
- Plan ahead for parking & food. Many of these are in small / neighborhood venues. Bring cash (some vendors may not take cards), arrive early, and bring patience.
- Support local. Many festivals feature local artisans, musicians, and food vendors. Buying that pie, apple, or handcrafted item helps keep our local culture thriving.
Why Fall in Winona Feels Special
Because autumn doesn’t just change the leaves here — it brings the perfect backdrop: the Mississippi River, bluff views, crisp air, and a sense of slowing down. These festivals aren’t just fun, they’re ways we reconnect — with our history, with neighbors, and with the landscape that makes Winona unique.
