TOP 30 Wine bar in Leonardtown, Maryland

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Port of Leonardtown Winery is a charming destination located in Leonardtown, Maryland, United States. Situated at 23190 Newtowne Neck Road, this institution is a unique combination of a winery, food and liquor store, and a popular tourist attraction. Visitors can enjoy a variety of locally produced wines, delicious food options, and browse through an array of liquor offerings. The picturesque surroundings and welcoming atmosphere make it the perfect spot for a relaxing day out or a special event. Whether you're a wine connoisseur or just looking for a fun outing, Port of Leonardtown Winery has something for everyone.

The Front Porch is a charming institution located in historic downtown Leonardtown, Maryland. This intimate restaurant offers creative Southern Coastal Cuisine in a cozy atmosphere within the Sterling House. Our friendly staff provides gracious service, making guests feel welcome and at home. As a gathering place for the community, The Front Porch serves fresh and quality ingredients at an affordable price. The décor is warm and inviting, with local photography and artifacts on display, showcasing the beauty and history of St. Mary's County.

Olde Town Pub is a cozy and inviting bar, food, and restaurant located at 22785 Washington Street in Leonardtown, Maryland. This charming establishment offers a laid-back atmosphere where patrons can enjoy delicious food, refreshing drinks, and good company. Whether you're looking to grab a bite to eat, have a few drinks with friends, or catch a game on TV, Olde Town Pub has something for everyone. With its friendly staff and welcoming ambiance, it's the perfect spot to unwind and relax in the heart of Leonardtown.

Friendly Tavern & Liquors is a cozy and welcoming bar located in Waldorf, Maryland. With a laid-back atmosphere and friendly staff, this establishment is the perfect spot to unwind and enjoy a drink with friends. Whether you're looking for a cold beer, a refreshing cocktail, or a glass of wine, Friendly Tavern & Liquors has you covered. The bar also offers a selection of liquors for those looking to enjoy a shot or two. Stop by 3190 Leonardtown Road and experience the friendly vibes and great drinks that this neighborhood bar has to offer.

Ironwood Grill is a cozy and inviting bar and restaurant located in Leonardtown, Maryland. Situated at 21935 Society Hill Road, this establishment offers a diverse menu of delicious food and drinks in a relaxed and welcoming atmosphere. Whether you're looking for a casual meal with friends or a night out on the town, Ironwood Grill has something for everyone. Come enjoy a tasty meal and a refreshing drink at this popular local spot.