Deadwood's Main St Wine and Chocolate Stroll Tickets

You're a few taps away from a memorable afternoon in Deadwood. Deadwood's Main St Wine and Chocolate Stroll is a 21+ celebration of wine, cheese, and chocolate across 19 participating locations on Deadwood's historic Main Street. Registration is at the Deadwood Welcome Center, 501 Main Street, and tickets include tastings at all venues plus a commemorative wine glass. Proceeds benefit Deadwood’s Main Street Initiative (MSI). The event runs from 1:00 PM to 6:00 PM in 2026 (check listings for 2025 times). Tickets are sold via Eventbrite, and venue menus are updated on official pages as the event approaches. Secure your seats and join fellow enthusiasts for an insider’s tour through Deadwood’s vibrant tasting scene.

About the performer: Deadwood's Main St Wine and Chocolate Stroll is more than an event—it’s a community celebration that blends local hospitality with curated pairings. Follow the Stroll on official social channels for updates, menus, and behind-the-scenes looks at participant locations. Whether you’re a local or visiting, this tour offers a relaxed, 21+ environment to explore Deadwood’s Main Street while enjoying wine, cheese, and chocolate pairings. For booking inquiries, we’re here to help you secure your tickets and plan your day—consider us your go-to connection in the business of Deadwood events.