Fun in Leonardtown

You won't want to miss great events and activities in the heart of St. Mary's County, charming Historic Leonardtown.


Centrally located, Leonardtown serves as a convenient hub. The town received its moniker “a most convenient place” back in the early 18th century, and visitors and locals alike know that how true this slogan is! With numerous restaurants, art galleries, a hotel, a quaint town square, a winery, a wharf and water trail along Breton Bay, shops, historic sites, events and more, Leonardtown offers fun for all ages.

Eat: Fantastic Food

From fine cuisine to pub grub, your dining options in Leonardtown are many. Learn More

Stay: Central Site

With an in-town hotel just footsteps away from the Town Square, "A Most Convenient Place" certainly describes Executive Inn & Suites Leonardtown! Learn More

Browse: Shop on the Square

Find local shops, art galleries, and other shopping opportunities right in the heart of town. LEARN MORE

Do: Awesome Activities

A winery, historic sites, kayaking (seasonal), historic sites and more. There is no shortage of activities in this little town. Learn More

Learn more about all there is to do in Leonardtown!