Wine, Cheese and Chocolate Stroll

If your idea of a perfect Saturday involves premium wines served in a commemorative Riedel glass and paired with artisan chocolates, mark the third Saturday of February on your calendar.

The Wine, Cheese and Chocolate Stroll takes place February 21, 2026 and transforms Deadwood’s Main Street into a walkable tasting room. A total of 19 participating locations offer carefully curated pairings during this popular event.

The stroll is a fundraiser for Deadwood’s Main Street Initiative. Tickets cost $60 per person and participation is capped at 300 guests. The event sells out every year, so tickets should be purchased through Eventbrite as soon as they are released.

Registration runs from noon to 3:00 PM at the Deadwood Welcome Center located at 501 Main Street. Participants show identification, sign a waiver, and receive their keepsake glass. From there, guests can stroll at their own pace until 6:00 PM.

The wine selections are notably strong. Saloon No. 10 at 657 Main Street pours Jeio Prosecco Superiore alongside Austin Hope Cabernet Sauvignon. The Midnight Star features Santa Margherita Pinot Grigio and Orin Swift 8 Years in the Desert. The Franklin Hotel uncorks Caymus Cabernet, while local producers are also well represented.

Belle Joli Winery at 594 Main Street, a family operated winery using Black Hills grapes, serves its Frontenac and Reserve Rosé. Naughti Wines at 692 Main Street brings playful selections such as Gay Rosé and Cherry Fantasy. Chocolate only stops at Pink Door Boutique and Madame Peacock’s provide sweet breaks between tastings.

All participants must be 21 or older. Guests are encouraged to pace themselves across the five hour event, wear comfortable shoes, and consider booking accommodations at the Celebrity Hotel at 629 Main Street or the Bullock Hotel to easily walk back to their room afterward.