The Town of Leonardtown has a host of fun things to do, from historic sightseeing to watersports to winery tours.

A little known secret hidden along the McIntosh Run in Leonardtown is the Port of Leonardtown Public Park. This developing passive park and winery is the launch point of a nearly three mile serene canoe/ kayak trail. As you paddle along the McIntosh Run you will pass thru a 58 acre FIDS (Forest Interior Dwelling Species) Habitat. This area is home to bald eagle families, Baltimore Orioles, wild turkeys and many other bird species. As you wind through this wooded trail you will be amazed by the peaceful tranquility. The trail terminates at the beautiful, new Leonardtown Wharf Public Park. Bring a picnic lunch or stroll up to Leonardtown Square and enjoy lunch at one of our many fine restaurants. Rentals and transportation available by McIntosh Outfitters and Hillside Ride.

Patuxent Adventure Center
Canoe and Kayak Rentals
Hillside Ride
Shuttle, Rental and Special Events

Open for business in Fall of 2009 the Port of Leonardtown Winery is home to the Southern Maryland Winegrowers Cooperative. A joint project of the Commissioners of Leonardtown and the St. Mary’s County Commissioners these facilities will offer local farmers an opportunity to grow grapes and cooperatively produce local wines as a co-op member.

Tour cultural sites - old and new - on the self- guided walking tour of Leonardtown’s history, heritage, and architecture. Traces of history can be found throughout the landscape, commercial buildings, churches, and residences. Leonardtown has a wealth of sights and experiences to educate and entertain.

Leonardtown is host to family oriented events year round. On the First Friday of each month, historic Leonardtown’s art galleries, restaurants, cafes, gift shops, antique shops, bookstores, etc. open their doors to showcase local artists and/or serve specials at their establishments. Join one of our fun filled events soon to see why thousands of people flock to Leonardtown for a unique hometown experience.

If there is a wedding or special event in your future consider an all inclusive Leonardtown event. Leonardtown offers florists, restaurants, catering, lodging, transportation, printing and beautiful ceremony sites.