A picturesque waterfront  with a spectacular view.

The heart of Downtown Historic Leonardtown.

This lush green park is a hidden gem in Leonardtown.

An indoor marketplace and community gathering space that provides a unique experience for visitors.

Explore a collection of specialty shops and enjoy the vibrant energy of this eclectic street.

Leonardtown, the only ARTS & ENTERTAINMENT DISTRICT in Southern Maryland, offers a rich experience in culture.

Discover Historic Landmarks, outdoor sculptures and works of art by local artists, and exciting activities in the Butterfly & kid's Caterpillar Trails.

Featuring Southern Maryland Wineries and Vineyards. Tour the vineyards and enjoy live music while sampling award-winning wines.

Begin your visit to Leonardtown at the Old Jail Museum and new Leonardtown Visitor's Center to learn all the wonderful things there are to see and do in this vibrant Southern Maryland Town. 

Enjoy a two-hour sunset cruise down Breton Bay to St. Clements Island with Fish the Bay Charters. Departing from Leonardtown Wharf, these BYOB, small-group cruises on the Lisa S. are a great way to relax and connect with friends and family. Spend 2 hours cruising aboard the Lisa S., a 48-foot vintage charter boat, with Captain Phil Langley. Bring your favorite snacks, drinks and adult beverages on board or pick up something on your way from one of our wonderful local restaurants and dine while enjoying the sights and sounds of St. Mary's County's beautiful waterways.

Spend a relaxing day or wind down for the evening at the Port of Leonardtown Winery. Sample award-winning wines or non-alcohol or frosé slushies while listening to live music. This charming Winery is nestled within the Port of Leonardtown Winery Park. Amenities include an outdoor pavilion with colorful umbrellas for shade, cornhole and other games, an indoor patio with fire pit to keep you warm on cooler evenings and a tasting room. Sample eats from local food trucks and vendors or pick something up from one of our local restaurants in Town. 

Rent a canoe or kayak from Pac Paddle Sports enjoy a day paddling along beautiful Breton Bay. A popular outing is along McIntosh Run, a picturesque water trail that leads all the way to Leonardtown Wharf and back. Travel a narrow creek under a canopy of trees along serene waterways that are home to Bald eagles, beavers, muskrats, and otter. Paddle with friends or meet others in regular group paddles and special events - frequent events include moonlight or sunrise paddles and other special events.