Leonardtown Itinerary

A most convenient place, indeed!

Centrally located, Leonardtown serves as a convenient hub featuring local shopping, dining, a winery, a quaint town square and a water trail along Breton Bay.

Shop the Town and Paddle Around

Back in the 1700s, Leonardtown became the center for local commerce and governance when the colonial capital moved from St. Mary’s City to Annapolis. Throughout the centuries, the town retained its small town charm and walkability. Places to visit include Tudor Hall, home of the local Historical Society, the Old Jail Museum, and the Wharf Park. Leonardtown is a state designated Arts & Entertainment District and offers galleries and local shops and restaurants.

The Port of Leonardtown Winery lies at the northern edge of town and shares its site with the input for McIntosh Run Water Trai which winds through woodland and estuaries on its way to Breton Bay. Newtowne Neck State Park is just down Maryland Route 243. The park sits along the Potomac River and here, you’ll find more opportunities to paddle, and also bird and beach comb.

Stay Longer

If you fall in love with the area, extend your visit with a stay at the Executive Inn & Suites Hotel Park Avenue, located right off the square in downtown Leonardtown.