Bar seating in Leonardtown, Maryland

Sweetbay Restaurant & Bar is a charming dining establishment located at 22680 Washington Street in Leonardtown, Maryland. This cozy restaurant offers a diverse menu of delicious dishes and refreshing drinks in a relaxing and inviting atmosphere. Whether you're looking for a casual meal with friends or a special dinner with a loved one, Sweetbay Restaurant & Bar is the perfect place to enjoy a memorable dining experience. Come and indulge in our mouthwatering cuisine and exceptional service at this popular food destination in Leonardtown.

The Leonardtown Grille is a charming restaurant located at 25470 Point Lookout Road in Leonardtown, Maryland. Known for its delicious cuisine and welcoming atmosphere, this establishment offers a diverse menu of classic American dishes with a modern twist. Whether you're looking for a casual lunch with friends or a special dinner with loved ones, The Leonardtown Grille is the perfect spot to enjoy a memorable dining experience. Come and savor the flavors of Maryland at this popular local eatery.

Leonardtown Cigars is a premier cigar store located at 40955 Merchants Lane in Leonardtown, Maryland. We offer a wide selection of high-quality cigars from around the world, as well as accessories and smoking lounges for our customers to enjoy. Whether you're a seasoned cigar aficionado or new to the world of cigars, our knowledgeable staff is here to help you find the perfect smoke for any occasion. Visit Leonardtown Cigars and indulge in a truly luxurious smoking experience.

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.

Mac's Tap & Table is a cozy and inviting restaurant located in Leonardtown, Maryland. Situated at 25470 Point Lookout Road, this establishment offers a unique dining experience with a focus on delicious food and a wide selection of craft beers on tap. Whether you're looking for a casual meal with friends or a special night out, Mac's Tap & Table has something for everyone. Come and enjoy a tasty meal in a warm and welcoming atmosphere at this popular dining spot in Leonardtown.

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.

Antoinette's Garden is a charming bar and food establishment located at 22694 Washington Street in Leonardtown, Maryland. This cozy spot offers a delightful ambiance with a lush garden setting, perfect for enjoying a relaxing meal or drinks with friends and family. The menu features a variety of delicious dishes and refreshing beverages, making it a popular choice for locals and visitors alike. Whether you're looking for a casual lunch or a fun night out, Antoinette's Garden is the perfect destination for a memorable dining experience.

Checker's Well is a cozy and welcoming restaurant located at 3002 Leonardtown Road in Waldorf, Maryland. Known for its delicious comfort food and friendly atmosphere, Checker's Well is the perfect spot for a casual meal with friends or family. Whether you're craving a juicy burger, crispy fries, or a refreshing milkshake, Checker's Well has something for everyone. Stop by and enjoy a satisfying meal in a laid-back setting at this popular eatery in Waldorf.

Better Black Coffee is a cozy cafe and food store located at 25805 Point Lookout Road in Leonardtown, Maryland. Our mission is to provide a welcoming space where customers can enjoy delicious coffee, pastries, and snacks while supporting black-owned businesses. Our menu features a variety of specialty coffee drinks, including lattes, cappuccinos, and cold brews, as well as a selection of baked goods and light bites. Whether you're looking for a quick pick-me-up or a place to relax and unwind, Better Black Coffee has something for everyone. Come visit us and experience the unique flavors and warm atmosphere that set us apart from other cafes in the area.