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Leonardtown has been described in many ways; small town charm, quaint, tranquil with historic roots. One of the best surprises is the hidden upscale draws. More than once described as a cross between Mayberry and Annapolis! With over 300 years of history there are plenty of historical sites to visit. But there is plenty more to do from outdoor life to shopping and dining. The downtown square, one of the few remaining intact in Maryland today, is a beautiful gathering place for residents and visitors. Whether it is for one of the numerous public events held annually there or just a quiet stroll along the brick paved sidewalks.

The downtown square boasts numerous restaurants to suit any palate! For the shopping enthusiasts there are specialty shops and galleries, antique stores, a used book and music store, a health food store and artisan shops. The newly opened Leonardtown Arts Center is home to several artists that not only sell their wares but also demonstrate their art. The Maryland Antique Center features numerous antique and art dealers all under one roof. Visit our award winning Port of Leonardtown Winery or paddle our nearly 3 mile water trail to Leonardtown Wharf Public Park.

There is much more of the Leonardtown story to tell. Explore this website or better yet come enjoy an afternoon exploring Leonardtown. It is definitely worth the trip!

Leonardtown Business Association

Leonardtown A Most Convenient Place