Things To Do
Best Places to Dine
The Front Porch Sweetbay Restaurant and Bar Il Piccolo Morso Olde Town Pub The Rex Kevin's Corner Kafe Ye Olde Towne Cafe (breakfast & lunch only)
Best Places to Unwind
Antoinette's Garden Port of Leonardtown Winery Brüdergarten (Brü) Social on Fenwick Frog Town Ice Cream Heritage Chocolates
Favorite Activities
Shepard's Old Field Market Breton Bay Golf & Country Club Patuxent Adventure Center
Historic Sites
The Old Jail Museum & Visitor Center St. Clements Island Moll Dyer's Rock at Tudor Hall
The Front Porch
Classic southern cuisine with historic charm
Sweetbay Restaurant & Bar
Upscale menu putting a spin on local cuisine; fantastic cocktails
IL Piccolo Morso
Delicious Italian fare
Olde Town Pub
Famous for their wings - Old Bay are a must try
The Rex
Historic movie theatre turned casual hangout for food and drink
Kevin's Corner Kafe
Just south of downtown, great Southern Maryland seafood
Ye Olde Towne Cafe
Leonardtown's best breakfast
Antoinette’s Garden
Wine and cocktail bar with small eats
Port of Leonardtown Winery
Just outside of downtown, Leonardtown's only winery often features live music on Friday nights
Brüdergarten (Brü)
Leonardtown's only beer garden offering artisan beers on tap and creative cocktails
Social
Coffeehouse and cocktail bar
Frog Town Ice Cream
Ice cream shop at Leonardtown Wharf
Heritage Chocolates
Shepherd's Old Field Market
Local shopping with more than 50 vendors
Breton Bay Golf & Country Club
Beautiful golf course overlooking Breton Bay
Patuxent Adventure Center Paddle Sports
Kayak down the McIntosh run to Leonardtown Wharf
The Old Jail Museum & Leonardtown Visitor Center
Visit the oldest sheriff's office in the nation that also played an instrumental role in the Underground Railroad in Maryland
St. Clement’s Island State Park
See where Father Andrew White led the first Catholic Mass in the 13 colonies
Moll Dyer Rock
Don't forget to visit Leonardtown's most legendary lady