Dog Events in Middleburg, VA

This guided wine hike invites guests 21+ and their leashed dogs to explore scenic vineyard trails while enjoying curated wine tastings at stops throughout the property. The hike is moderate+ and takes approximately one hour. Hiking or tennis shoes are required. Please bring water along for you and your pup.

This dog-friendly Halloween celebration features a pup costume parade, photo booth, treat bar, trick-or-treating, local pet vendors and festive photo opportunities. Guests can enjoy delicious cider while their pups show off their Halloween costumes and participate in the pet food drive. Visitors can also explore seasonal activities, farm animals and pumpkin patch adventures at Great Country Farms across the way.