Leonardtown MarylandATTRACTIONS & THINGS TO DO
Listed below are the best attractions and things to do near Leonardtown, Maryland.
1. Port of Leonardtown Winery
AWARD-WINNING LOCAL WINERY
Port of Leonardtown Winery is a celebrated destination offering tastings of locally produced wines in a relaxed, scenic setting. Guests can enjoy the beautiful vineyard views and often find live music or special events happening onsite. The winery is a favorite spot for both locals and visitors to unwind and sample award-winning wines.
2. Leonardtown Wharf Park
SCENIC WATERFRONT PARK
Leonardtown Wharf Park is a picturesque waterfront spot located at the edge of Breton Bay. Visitors can stroll along the boardwalk, relax by the water, or enjoy kayaking and paddleboarding. The park is also a popular site for community events and provides lovely views year-round.
3. Moll Dyer Rock
HISTORIC LOCAL LANDMARK
Moll Dyer Rock is a legendary stone associated with the story of Moll Dyer, a colonial-era woman believed to have been the victim of a witch trial. The rock is an important piece of local folklore and a point of interest for those intrigued by Leonardtown's haunted history. Visitors often seek out the stone to learn more about this mysterious tale and the town's past.
4. North End Gallery
LOCAL ART COLLECTIVE
North End Gallery is a well-known artists' cooperative featuring works in various media from talented regional artists. Guests are welcome to browse paintings, jewelry, pottery, and photography in a welcoming, light-filled space. The gallery frequently hosts themed exhibitions and interactive events for art enthusiasts.
5. Saint Mary's River State Park
OUTDOOR RECREATION HAVEN
Saint Mary's River State Park spans over 2,000 acres and includes a large freshwater lake surrounded by hiking and biking trails. Anglers, kayakers, and picnickers find this natural oasis perfect for a day of recreation or relaxation. The park also offers birdwatching and wildlife viewing opportunities throughout the year.
6. The Old Jail Museum & Leonardtown Visitor Center
HISTORIC JAIL & MUSEUM
The Old Jail Museum is housed in one of the oldest jails in Southern Maryland, dating back to the 1800s. This unique attraction offers insight into local history and law enforcement over the centuries. The onsite visitor center provides maps and information to help travelers explore Leonardtown and St. Mary's County.
7. Newtowne Neck State Park
TRANQUIL NATURAL RETREAT
Newtowne Neck State Park is a serene peninsula offering miles of shoreline and diverse habitats for hiking, fishing, and wildlife observation. The park is steeped in history, once the site of a colonial Jesuit settlement. Bird watchers and nature lovers enjoy the unspoiled landscapes and peaceful atmosphere.
8. Tudor Hall
HISTORIC MANSION TOUR
Tudor Hall is a beautifully preserved mansion that serves as the headquarters for the St. Mary's County Historical Society. Visitors can tour the stately rooms and learn about the region's colonial and Civil War-era heritage. The home's architecture and collections reflect centuries of local history and culture.
9. Shepherd's Old Field Market
ECLECTIC INDOOR MARKETPLACE
Shepherd's Old Field Market is a renovated historic warehouse now functioning as a bustling indoor market with specialty shops, an organic café, and gourmet burger joint. Shoppers can browse artisan goods, enjoy a refreshing drink at the beer garden, or try axe throwing at this unique destination. Regular special events and a vibrant community atmosphere make it a must-visit.
10. Leonardtown Square
HISTORIC TOWN CENTER
Leonardtown Square is the central hub of the town, surrounded by shops, restaurants, galleries, and historic landmarks. The square is a gathering place for festivals, outdoor concerts, farmers' markets, and the popular annual End of Summer Beach Party. Its charming streetscape and lively events showcase Leonardtown's welcoming spirit.
11. Fenwick Street
BOUTIQUE SHOPPING STREET
Fenwick Street is the place to explore a variety of local boutiques, quirky shops, and small eateries in downtown Leonardtown. The vibrant street features handcrafted goods, vintage finds, and friendly shopkeepers. A favorite for leisurely shopping and discovering unique Southern Maryland gifts.
12. Leonardtown Butterfly Trail
INTERACTIVE PUBLIC ART WALK
The Leonardtown Butterfly Trail leads visitors on a delightful stroll to view outdoor sculptures, artistic installations, and engaging activities designed for children and families. The trail highlights local creativity and the town's support for public art. It's an enjoyable way to experience Leonardtown's artistic side and get outdoors.
13. Social Coffeehouse
CHIC COFFEE & EATS
Social Coffeehouse is a trendy downtown café known for its expertly crafted coffee drinks, creative pastries, and light fare. The welcoming atmosphere makes it a beloved spot for both locals and visitors looking to relax or catch up with friends. Seasonal specialties and local artwork add to its cozy charm.
14. Sweetbay Restaurant and Bar
CONTEMPORARY AMERICAN DINING
Sweetbay Restaurant and Bar offers an upscale yet approachable dining experience with a menu focusing on fresh, locally sourced ingredients. The kitchen creates inventive takes on American classics alongside craft cocktails and curated wines. The stylish interior and attentive service make it a favorite for special occasions and casual gatherings alike.
15. Historic St. Mary's City
LIVING HISTORY MUSEUM
Historic St. Mary's City, just a short drive from Leonardtown, is Maryland's first colonial capital and now an extensive living history museum. Reenactors, archaeological sites, and reconstructed colonial buildings make history come alive for visitors of all ages. The museum's interactive programs and beautiful riverside setting provide a memorable glimpse into 17th-century Maryland.