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Wineries and Vineyards in Middleburg, VA

5 of the 10 wineries, breweries, distilleries and wine bars we list in Middleburg are wineries or tasting rooms.

Choosing a winery comes down to the style of visit you want, ranging from production vineyards with estate tours to standalone downtown tasting rooms. Places differ in whether they offer full food menus or simple cheese slates, require advance reservations, or welcome children and pets. A map location shows distance, but it will not tell you if a spot focuses on casual pour flights or structured, guided cellar tastings.

  1. 50 West Vineyards

    39060 Little River Tpke, Middleburg, VA 20117-2918

    Mon 12-5, Thu-Sun 11am-8pm

    TastingsFood servedPrivate events
    Call Website Directions

  2. Chrysalis Vineyards

    39025 Little River Tpke, Middleburg, VA 20117-2919

    Mon-Thu 12-6, Fri-Sun 12-7/8

    TastingsFood servedPrivate events
    Call Website Directions

  3. Greenhill Vineyards

    23595 Winery Ln, Middleburg, VA 20117-2847

    Daily 12pm-6pm

    Food servedPrivate events
    Call Website Directions

  4. Cana Vineyards and Winery

    38600 Little River Tpke, Middleburg, VA 20117-2916

    Call Website Directions

  5. The Ag District Center at Chrysalis Vineyards

    Middleburg, VA

    Directions
Check reservation policies early. Many vineyard tasting rooms require advance bookings on weekends, especially for groups larger than six or for guided estate tours.

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Good to know

What is the difference between a winery and a tasting room?

A winery is where the wine is actually produced and aged, often located on a vineyard estate. A tasting room may be located off-site in an urban area, serving as a retail location to sample and purchase wines made elsewhere.

Do wineries allow children and non-drinkers?

Policies vary widely by location. Many estate vineyards with large outdoor lawns welcome families and offer non-alcoholic beverages, while smaller or high-end tasting rooms may restrict access to adults aged 21 and over.

How much does a typical wine tasting cost?

Standard tasting flights often range from $15 to $35 per person, depending on the region and the wines poured. Higher-end reserve tastings or private cellar tours can cost significantly more, though fees are sometimes waived with a minimum bottle purchase.