TOP City restaurants in Leonardtown, Maryland

The Inn at Leonardtown, Ascend Hotel Collection is a charming lodging option located at 41655 Park Avenue in the historic town of Leonardtown, Maryland, United States. This boutique hotel offers comfortable and stylish accommodations, perfect for both leisure and business travelers. The Inn features modern amenities, personalized service, and a convenient location near local attractions, shops, and restaurants. Guests can enjoy a relaxing stay in a peaceful setting, with easy access to the beauty and charm of Southern Maryland. Whether you're visiting for a weekend getaway or a business trip, The Inn at Leonardtown offers a welcoming and memorable experience for all guests.

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.

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.

Happy Dragon Restaurant is a cozy and welcoming eatery located at 40955 Merchants Lane in Leonardtown, Maryland. Specializing in delicious Chinese cuisine, this restaurant offers a wide variety of traditional dishes that are sure to satisfy your cravings. Whether you're in the mood for savory stir-fry, flavorful noodles, or mouth-watering dumplings, Happy Dragon Restaurant has something for everyone. With friendly service and a warm atmosphere, this restaurant is the perfect spot for a casual meal with friends or family. Come visit us and experience the taste of authentic Chinese flavors at Happy Dragon Restaurant.

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 Burchmart is a convenient one-stop destination for all your food, gas, and dining needs. Located at 25355 Point Lookout Road in Leonardtown, Maryland, this institution offers a wide range of services including a gas station, a variety of food options, and a restaurant for sit-down meals. Whether you're looking to refuel your car, grab a quick snack, or enjoy a delicious meal, Leonardtown Burchmart has you covered. With its convenient location and diverse offerings, it's the perfect place to stop by while on the go.

Leonardtown Village is a charming institution located at 41485 Connelly Street in Leonardtown, Maryland, United States. This historic village offers a unique blend of old-world charm and modern amenities, making it a popular destination for visitors and residents alike. With its picturesque streets lined with shops, restaurants, and galleries, Leonardtown Village is a vibrant hub of activity and culture. Whether you're looking to explore the local history, enjoy a delicious meal, or shop for unique gifts, Leonardtown Village has something for everyone. Come and experience the beauty and charm of Leonardtown Village for yourself!

Tobacco King and Vape is a unique institution located at 3615 Leonardtown Road in Waldorf, Maryland. This establishment offers a variety of services including food, meal takeaway, restaurant, and store all in one convenient location. Customers can enjoy a delicious meal, grab a quick bite to eat, or stock up on tobacco and vape products. With a diverse menu and a wide selection of products, Tobacco King and Vape is a one-stop shop for all your dining and shopping needs. Visit us today to experience the best of both worlds!

Smash House is a vibrant and welcoming restaurant located at 22725 Duke Street in Leonardtown, Maryland. Known for its delicious and unique dishes, Smash House offers a diverse menu of mouth-watering food items that are sure to satisfy any craving. Whether you're in the mood for a juicy burger, crispy fries, or a refreshing salad, Smash House has something for everyone. With its cozy atmosphere and friendly staff, this institution is the perfect spot to enjoy a meal with friends and family. Come visit Smash House and experience the taste of Maryland's finest cuisine!

Do Dah Deli is a charming and cozy institution located at 22845 Washington Street in Leonardtown, Maryland. This unique establishment serves as a combination food deli, restaurant, and store, offering a wide variety of delicious and freshly made items. From gourmet sandwiches and salads to specialty snacks and beverages, Do Dah Deli has something for everyone to enjoy. With a warm and inviting atmosphere, friendly staff, and top-notch customer service, this institution is the perfect spot to grab a quick bite to eat or pick up some tasty treats to take home. Visit Do Dah Deli today and experience a culinary delight like no other.

The Slice House is a cozy and inviting restaurant located at 41565 Park Avenue in Leonardtown, Maryland. Specializing in delicious pizzas and other savory Italian dishes, this eatery offers a casual dining experience perfect for families, friends, and pizza lovers alike. With a diverse menu featuring a variety of toppings and flavors, The Slice House is sure to satisfy your cravings for a tasty meal. Come visit us and enjoy a slice of happiness!

Brüdergarten (Brü) is a lively and welcoming bar, food, and restaurant located at 22725 Duke Street in Leonardtown, Maryland. This institution offers a cozy and inviting atmosphere where guests can enjoy a variety of delicious dishes and refreshing drinks. Whether you're looking for a casual meal with friends, a night out with live music, or a relaxing evening with a craft beer, Brüdergarten has something for everyone. Come visit us and experience the warm hospitality and tasty cuisine that make Brü a favorite spot in the community.

Social on Fenwick is a charming establishment located in Leonardtown, Maryland. As a versatile institution, it serves as a bakery, bar, cafe, restaurant, and store all in one. The cozy atmosphere and friendly staff make it the perfect place to grab a coffee, enjoy a meal, or pick up some delicious baked goods. Whether you're looking for a quick bite to eat or a relaxing evening out, Social on Fenwick has something for everyone. Come visit us at 41658 Fenwick Street for a delightful dining experience.

The Slice House II Go is a popular eatery located at 22745 Washington Street in Leonardtown, Maryland. This restaurant specializes in delicious, freshly baked pizzas and other Italian favorites available for takeaway. Whether you're in the mood for a classic pepperoni pizza or a gourmet specialty pie, The Slice House II Go has something for everyone. With a convenient location and mouthwatering menu options, this institution is a must-visit for anyone craving a satisfying meal on the go.

Bon AppéSweet is a charming cafe, food store, and restaurant located at 25805 Point Lookout Road in Leonardtown, Maryland. This cozy establishment offers a wide range of delicious treats, including freshly baked pastries, gourmet sandwiches, salads, and specialty desserts. Whether you're looking for a quick bite to eat or a relaxing meal with friends, Bon AppéSweet has something for everyone. Stop by and indulge in their delectable offerings in a warm and inviting atmosphere.

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.

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.

IL Piccolo Morso is a charming Italian restaurant located at 22845 Washington Street in Leonardtown, Maryland. Known for its delicious and authentic cuisine, IL Piccolo Morso offers a cozy and inviting atmosphere for diners to enjoy a taste of Italy. From homemade pastas to savory meat dishes, each bite is a true delight for the taste buds. Whether you're looking for a romantic dinner for two or a family gathering, IL Piccolo Morso is the perfect spot to satisfy your cravings for Italian fare. Come visit us and experience a little taste of Italy right here in the United States.

Quality Carryout is a popular food establishment located at 3314 Leonardtown Road in Waldorf, Maryland. Known for its delicious and convenient carryout options, this restaurant offers a wide variety of dishes to satisfy any craving. From savory sandwiches and hearty salads to flavorful entrees and tasty sides, Quality Carryout is the perfect spot to grab a quick and satisfying meal on the go. With a focus on quality ingredients and exceptional customer service, this institution is a favorite among locals and visitors alike. Visit Quality Carryout today for a delicious dining experience you won't soon forget.

Randy's Ribs & BBQ is a beloved dining destination located at 7732 Leonardtown Road in Hughesville, Maryland. This cozy restaurant specializes in mouthwatering ribs and BBQ dishes that are sure to satisfy any craving. With a warm and welcoming atmosphere, Randy's Ribs & BBQ is the perfect place to enjoy a delicious meal with family and friends. Whether you're in the mood for tender ribs, juicy pulled pork, or flavorful BBQ chicken, this institution has something for everyone. Come experience the savory flavors and friendly service that make Randy's Ribs & BBQ a must-visit spot in Maryland.

Fitzie's Marina & Pub is a charming waterfront restaurant located in Leonardtown, Maryland. Situated at 21540 Joe Hazel Road, this institution offers a unique dining experience with beautiful views of the marina. Guests can enjoy a delicious meal while soaking in the serene atmosphere of the waterfront. The menu features a variety of pub-style dishes, seafood specialties, and refreshing drinks. Whether you're looking for a casual meal with friends or a romantic dinner with a loved one, Fitzie's Marina & Pub is the perfect spot to relax and unwind by the water.

Salsa's Mexican Café is a vibrant and inviting restaurant located in Leonardtown, Maryland. Known for its authentic Mexican cuisine and lively atmosphere, Salsa's offers a wide range of delicious dishes such as tacos, burritos, enchiladas, and more. The restaurant is a popular spot for locals and visitors alike, with friendly staff and a cozy dining area. Whether you're craving a traditional Mexican meal or looking to try something new, Salsa's Mexican Café is the perfect place to satisfy your taste buds. Visit us at 25470 Point Lookout Road for a taste of Mexico in the heart of Leonardtown.

Tropical Smoothie Cafe is a vibrant and energetic cafe located at 3390 Leonardtown Road in Waldorf, Maryland. We are currently seeking fun and enthusiastic crew members to join our team and help spread the sunshine! Our menu features craveable rewards, exclusive offers, and Tropic Time news. Indulge in our new Tropic Bowls, including Acai, Chia Oatmeal Pudding, Green Dream Yogurt, and Mixed Berry Greek Yogurt Bowls. You can order ahead in our app or online for pickup or delivery. Enjoy a sunshine-filled breakfast with our smoothies, wraps, and flatbreads available all day. Sign up for Tropic Rewards to earn points with every qualifying order and score free tropic favorites. Our made-to-order wraps and flatbreads are sure to boost your mood and make eating better easy. With customizable smoothies and fresh ingredients, we're blending up sunshine all day long. Visit us or access our app for a taste of the tropics today!

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.

Noli's is a charming establishment located at 26005 Point Lookout Road in Leonardtown, Maryland. This versatile institution offers a wide range of services including a bakery, bar, food, meal takeaway, restaurant, and store all under one roof. Whether you're looking for freshly baked goods, a delicious meal to enjoy on the go, or a relaxing drink at the bar, Noli's has something for everyone. Come visit us and experience the warm hospitality and delectable offerings that make Noli's a popular destination in Leonardtown.

Silvestre Chicken, located at 3617 Leonardtown Road in Waldorf, Maryland, is a top-rated restaurant known for its delicious rotisserie and grilled dishes. At Silvestre Rotisserie & Grill, we pride ourselves on using only the freshest and natural ingredients to create mouthwatering meals for our customers. Whether you're stopping by for lunch or dinner, you can always count on receiving excellent service in a clean and welcoming environment. Come experience the flavors of Silvestre Chicken for yourself!

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.

The Shops at Breton Bay is a charming shopping mall located at 40845 Merchants Lane in Leonardtown, Maryland. This destination offers a variety of shops, restaurants, and services for visitors to enjoy. With a mix of local boutiques and well-known brands, shoppers can find everything they need in one convenient location. Whether you're looking for the latest fashion trends, unique gifts, or a delicious meal, the Shops at Breton Bay has something for everyone. Come explore this vibrant shopping destination in the heart of Leonardtown.

Ledo Pizza is a popular restaurant located at 25460 Point Lookout Road in Leonardtown, Maryland. Known for their delicious pizzas and Italian cuisine, Ledo Pizza offers a wide variety of options for both dine-in and takeout. Whether you're craving a classic pepperoni pizza or a hearty pasta dish, Ledo Pizza has something for everyone. With their friendly staff and cozy atmosphere, it's the perfect spot to grab a meal with family and friends. Visit Ledo Pizza today for a satisfying dining experience in Leonardtown.