A little-known gem along the McIntosh Run in Leonardtown is the Port of Leonardtown Public Park. This developing passive park and winery serves as the launch point for a nearly three-mile serene canoe/kayak trail. As you paddle, you'll pass through a 58-acre Forest Interior Dwelling Species (FIDS) Habitat, home to bald eagles, Baltimore Orioles, wild turkeys, and many more native birds.
This wooded water trail provides a uniquely peaceful experience and concludes at the Leonardtown Wharf Public Park. Bring a picnic or stroll up to Leonardtown Square for lunch at one of the town's many charming restaurants. Rentals and shuttle services are available through McIntosh Outfitters and Hillside Ride.
Since its opening in Fall 2009, the Port of Leonardtown Winery has served as home to the Southern Maryland Winegrowers Cooperative—a joint venture by the Commissioners of Leonardtown and St. Mary's County. This co-op enables local farmers to grow grapes and collaboratively produce wines, showcasing the best of the region.
Leonardtown invites you to tour its rich cultural and historical landscape through a self-guided walking tour. Discover the town's heritage and architecture across churches, residences, and commercial buildings that still echo the past.
All year long, family-friendly events bring the community together. One highlight is First Fridays, where local art galleries, cafes, gift shops, and more showcase local artists and offer special promotions. These gatherings provide a perfect way to enjoy Leonardtown’s welcoming spirit and hometown charm.