Trip Ideas
Leonardtown is a gorgeous downtown area with local shops, great local dining, a waterfront park, winery, and much more all within walking distance!
Discover where bourbon first started and where grapes for wine were first planted in Maryland! Taste the history here in St. Mary's County.
If you are looking for one-of-a-kind, locally-made items, antiques and more, you'll find it in St. Mary's!
Where Historic Adventure Awaits.
St. Mary's, MD
Explore the Coast
Welcome to St. Mary's County! This Chesapeake Bay destination is brimming with history, outdoor fun, vibrant culture - and passionate people eager to share it all with you. Just a short drive from Washington, D.C., discover the mid-Atlantic's best kept travel secret.
Find Inspiration, adventure and excitement where the Potomac and the Chesapeake meet. Whether you have come to explore the past, savor the beauty of the moment, or imagine possibilities in the future, you will find that you are always welcome in St. Mary's, Maryland.
Jan 22
Appraiser Fair at St. Clement's Island Museum
You may have a hidden treasure in your attic or garage and not even know it! Visit with expert appraisers as they determine the value of your prized...
Jan 22
Live Music at Port of Leonardtown Winery
Spend your Saturday afternoon drinking award-winning wine and listening to Ben Connelley at Port of Leonardtown Winery. Come dance the afternoon away and try...
Jan 23
Live Music at Port of Leonardtown Winery
Spend your Sunday afternoon drinking award-winning wine and listening to Justin Allen at Port of Leonardtown Winery. Come dance the afternoon away and try the...
Feb 4
Explore Downtown Leonardtown on First Friday! Come enjoy dinner at one of the many local restaurants, enjoy a drink from Social Coffeehouse or Antoinette's...
Feb 11 - Feb 27
The Newtowne Players Theater Presents Puffs
Puffs is an original comedy that takes place in a familiar world and yet it is a world of it's own creation. It is hilarious and heartwarming, funny,...
Mar 4
Explore Downtown Leonardtown on First Friday! Come enjoy dinner at one of the many local restaurants, enjoy a drink from Social Coffeehouse or Antoinette's...
