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Wineries and Vineyards in Leonardtown, MD

3 of the 5 wineries, breweries, distilleries and wine bars we list in Leonardtown 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. Port of Leonardtown Winery

    23190 Newtowne Neck Rd, Leonardtown, MD 20650

    Daily 12-6pm

    TastingsPrivate events
  2. Jubilee Farm Fermentations

    19860 Pear Hill Rd, Leonardtown, MD 20650-4657

  3. Slack Farms

    19860 Pear Hill Rd, Leonardtown, MD 20650-4657

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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Wineries and Vineyards near Leonardtown

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.