Best events in

Delaplane

With its unhurried pace and focus on outdoor activities, there are plenty of events and things to do in Delaplane, VA. The local culture revolves around its expansive country estates, numerous wineries, and a strong equestrian heritage. From daytime agricultural festivals to quiet evenings perfect for stargazing, the area offers a relaxed alternative to city life.

• Spend an afternoon exploring the rolling hills of the Middleburg American Viticultural Area, where local wineries like Barrel Oak Winery, Blue Valley Vineyard, and Delaplane Cellars host tastings and social gatherings.
• Enjoy outdoor pursuits at Sky Meadows State Park, a designated Dark Sky Park, or visit a local spot like Hollin Farms for seasonal pick-your-own produce.
• Catch a recurring stand-up show at Three Fox Vineyards & Brewery, which hosts the Next Stop Comedy series.