November 2026

After a successful first year, Winona Con is making its return to the Driftless Region from November 20–22, 2026, bringing three days of gaming, creativity, and community to downtown Winona. Hosted by Driftless Tabletop, the convention will celebrate the diverse world of tabletop gaming, from board games and card tournaments to role-playing adventures and miniatures. Organizers say the event will highlight the region’s growing gaming culture while offering a welcoming space for families, hobbyists, and seasoned players alike.

The convention will feature open play areas, scheduled tournaments, and guided sessions for newcomers eager to learn new games. Vendors and local creators will showcase their work, offering everything from handcrafted dice and accessories to regional art and collectibles. With Driftless Tabletop’s focus on inclusivity and family fun, Winona Con aims to be more than just a gaming event—it’s a celebration of community, imagination, and the unique spirit of the Driftless Region.

Community leaders and organizers see the return of Winona Con as a milestone for Winona’s cultural calendar. By combining the energy of a convention with the warmth of local hospitality, Driftless Tabletop hopes to establish Winona Con as an annual tradition that strengthens connections across generations and neighborhoods. Whether attendees come to roll dice, shop for unique finds, or simply share in the excitement, the 2026 convention promises to be a vibrant showcase of creativity and camaraderie.