Things to see and do at Leonardtown, Maryland
Leonardtown, Maryland: History, Waterfront, and Small-Town Charm
Located in St. Mary’s County, Leonardtown, Maryland is a vibrant small town known for its historic square, lively arts scene, and scenic waterfront on Breton Bay. As the county seat, Leonardtown combines rich colonial history with modern attractions, making it a favorite destination in Southern Maryland for travelers who want culture, dining, and outdoor recreation all in one place.
Why Visit Leonardtown, MD?
Leonardtown is best known as the “only incorporated town in St. Mary’s County”, and it has become a hub for food, shopping, and community events. With its walkable downtown, waterfront park, and strong ties to Maryland’s early history, Leonardtown offers the perfect mix of past and present.
Just over an hour from Washington, D.C. and two hours from Baltimore, Leonardtown makes an excellent weekend getaway for city dwellers looking to slow down and enjoy the Southern Maryland lifestyle.
Top Things to Do in Leonardtown, Maryland
1. Stroll Historic Downtown
At the heart of Leonardtown is its historic town square, lined with shops, galleries, and restaurants. The square often hosts festivals, parades, and community gatherings, giving visitors a chance to experience the town’s welcoming charm.
2. Visit Leonardtown Wharf Park
The Leonardtown Wharf is one of the town’s most scenic spots, located along Breton Bay. Visitors can enjoy walking trails, fishing, kayaking, or simply relaxing with waterfront views. The wharf is also a prime location for concerts and seasonal events.
3. Experience Local Art and Culture
Leonardtown has a growing reputation as an arts and entertainment district. Local galleries, studios, and cultural venues showcase regional artists and host workshops. The town’s focus on the arts makes it a lively and creative place to explore.
4. Enjoy Dining and Wineries
Food lovers will find plenty to enjoy in Leonardtown. From farm-to-table restaurants to seafood eateries, the town highlights Southern Maryland flavors. Just outside town, visitors can explore nearby wineries and breweries, including the popular Port of Leonardtown Winery.
5. Explore St. Mary’s County History
Leonardtown makes an excellent base for exploring St. Mary’s County’s colonial history. Sites like Historic St. Mary’s City and St. Clement’s Island—the birthplace of Maryland—are just a short drive away.
Visitor Information
- Location: Southern Maryland, in St. Mary’s County.
- Best Time to Visit: Spring and summer for festivals and water activities; fall for wine tours and scenic drives.
- Events: Leonardtown hosts events year-round, including the Annual Beach Party on the Square, art festivals, and holiday parades.
Plan Your Trip to Leonardtown, Maryland
With its historic downtown, waterfront views, and thriving arts scene, Leonardtown, Maryland is more than just a small town—it’s a destination full of charm and activity. Whether you’re kayaking on Breton Bay, sampling local wines, or strolling the historic square, Leonardtown offers a refreshing mix of culture, history, and natural beauty in the heart of Southern Maryland.
Thinking of visiting? Viator offers numerous tours in Maryland. Click here for details. vi.me/LeEvP
Leonardtown Wharf Park
Leonardtown Wharf Park on Breton Bay
Breton Bay