A Georgian mansion overlooking Breton Bay, historic landmarks, and a three-mile waterway offer different starting points for your trip to Leonardtown. County history and art are in the spotlight here, alongside opportunities for paddling and wildlife viewing. Each experience has its own focus: Tudor Hall and the Old Jail tell stories of the past, while the Leonardtown A&E District, the Butterfly Trail, and the waterways reveal other sides of the town.
Mansions and County History
Tudor Hall is a Georgian mansion overlooking Breton Bay and home to the St. Mary’s County Historical Society. It is also considered an important 18th-century house in St. Mary’s County. The building brings together its architecture, its present-day use by the historical society, and its significance to the county.
The Old Jail offers a different historical focus. It was expanded in 1876 and served as the St. Mary’s County jail until 1942. Today, it is preserved as a museum and is one of Leonardtown’s best-known historic landmarks. Visitors can start the Leonardtown Butterfly Trail at the Leonardtown Visitor Center in the Old Jail Museum.
Art and Discoveries Around Town
The family-friendly Leonardtown Butterfly Trail highlights historic landmarks, outdoor spaces, local art, local businesses, and other discoveries in Leonardtown. The Leonardtown A&E District includes the St. Mary’s Arts Council, art galleries, studios, shops, and restaurants. The trail draws attention to different aspects of the town, while the district brings together art and local businesses.
Leonardtown’s First Fridays also combine a chic artistic vibe with the charm of Southern Maryland. Alongside the galleries and studios in the A&E District, art enthusiasts can find another cultural offering that connects Leonardtown with the region.
Waterways and Paddling
At McIntosh Run, Port of Leonardtown Winery Park has a launch site for canoes and kayaks. A scenic three-mile waterway runs from McIntosh Run to Leonardtown Wharf. This provides two distinct points of reference for spending time on the water: a specific launch site and a described water route.
Rental options also vary by location: Patuxent Adventure Center offers kayak and paddleboard rentals at Leonardtown Wharf, and kayak rentals at McIntosh Run. In the paddling area on McIntosh Run and in Breton Bay, you may spot bald eagles, beavers, muskrats, herons, and, occasionally, river otters. In addition to the route and rentals, potential wildlife sightings are another consideration when planning.
Lessons and Horse Leasing
Alongside history, art, and water, A Moment In Time offers a year-round lesson and horse-leasing program for all skill levels. For travelers interested in horseback riding, this offers a different activity from the cultural attractions or the opportunities on the water. The year-round schedule and skill levels mentioned apply to this lesson and leasing program.
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Return to the main travel guide: Saint Mary's County.
