Downtown Fun in St. Mary's County Itinerary
Spend a day, or two, in Downtown Leonardtown! Enjoy dining, shopping, history, wine, and more!
Start your morning off with a cup of coffee and breakfast at Social Coffeehouse and Bar. From a wide variety of coffee, tea, pastries, and more, there's something for everyone.
Take a short walk from Social Coffeehouse down to the Leonardtown Wharf. Take in the beautiful waterfront scene as you finish your morning coffee. Kayaking and paddle boarding from the wharf is available and you can purchase rentals from Patuxent Adventure Center.
Enjoy a bit of history with the Old Jail Museum and the Moll Dyer Rock. The Old Jail Museum is the oldest sheriff's station in the nation and is also an Underground Railroad Network to Freedom Site. The Moll Dyer Rock is said to be cursed by a woman named Moll Dyer who was accused of witchcraft by the local town people in the 1600's.
Enjoy shopping at the unique Shepherd's Old Field Market. Home to over 50 different shops, there is something for everyone. Shepherd's Old Field Market is also home to Botanic Deli and Brudergarten Beer Garden.
Grab a delicious bite to eat from Botanic Deli right in Shepherd's Old Field Market! From daily specials to sandwiches to amazing beverages, a great lunch stop in Leonardtown! Take your lunch and enjoy it in the Leonardtown Square that has seats and benches for you to admire Downtown while you eat.
Fenwick Street Used Books and Music Store is an amazing local shop full of books, music, DVDs, and so much more. A great stop of all book lovers!
North End Gallery is the oldest art gallery in St. Mary's County offers a diverse collection of original fine art, jewelry, and crafts by as many as 35 juried artists and artisans from Southern Maryland. A great place to visit and take home unique and handmade art.
Craving something sweet on your trip? Stop by Heritage Chocolates! Handcrafted chocolates and gelato of a wide variety!
Wine and unwind at Port of Leonardtown Winery! Enjoy award winning wine at the first commercial winery in St. Mary's County!
Enjoy pre-dinner drinks at Antoinette's Garden! Enjoy a wide selection of wine and mixed beverages paired with a delicious charcuterie board.
Enjoy a fine dining experience paired with a delicious dinner at Sweetbay Restaurant and Bar.
Finish the night off at the Brudergarten Beer Garden at Shepherd's Old Field Market. Enjoy a wide variety of local craft beers, artisan wines, creative cocktails, and delicious bites.
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