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.

Social Coffeehouse

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.

Leonardtown Wharf

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.

Old Jail Museum

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.

Shepherd's Old Field Market

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.

Botanic Deli

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!

Fenwick Used Books and Music Store

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.

North End Gallery

Craving something sweet on your trip? Stop by Heritage Chocolates! Handcrafted chocolates and gelato of a wide variety!

Heritage Chocolates

Wine and unwind at Port of Leonardtown Winery! Enjoy award winning wine at the first commercial winery in St. Mary's County!

Port of Leonardtown Winery

Enjoy pre-dinner drinks at Antoinette's Garden! Enjoy a wide selection of wine and mixed beverages paired with a delicious charcuterie board.

Antoinette's Garden

Enjoy a fine dining experience paired with a delicious dinner at Sweetbay Restaurant and Bar.

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.

Brudergarten Beer Garden

Want to do the Downtown Fun Itinerary?

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Want to Create Your Own Downtown Fun Itinerary?

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