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Town Attractions

History of Leonardtown

Port of Leonardtown

Winery, Wharf, Water Trails

First Fridays



Raiders & Invaders Vendor Application Form

Spring Fling Classic Car Show
Sunday, April 27, 2014
 am to 4 pm

Town Election Day
May 6, 2014
12:00 p.m. to 7:00 p.m.

June 6-8, 2014
Three days of fun add up to one fantastic weekend.  Friday and Saturday in Leonardtown, it's music, street theater, food, brews and fun along the waterfront. Sunday, experience the rich history and culture of the entire St. Mary's peninsula. It's all just a short drive south of D.C. and Baltimore.
Learn More About the Event

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!

Printable Calendar of Events for 2014

Leonardtown Business Association

Leonardtown A Most Convenient Place

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St, Mary's County Tourism Information

Maryland Tourism Information

First Fridays In Leonardtown
First Friday of Every Month, 5pm - 8pm
Many shops, galleries and restaurants have joined together to celebrate First Fridays in Leonardtown. New businesses are joining the party every month! Join us for Art, food, shopping and socializing while exploring the nooks and crannies of Leonardtown. Visit the First Fridays website for detailed information.


41660 Courthouse Drive, P.O. Box 1, Leonardtown, MD 20650 301-475-9791 FAX: 301-475-5350
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