Leonardtown Square is the heart of historic downtown Leonardtown. One of the few remaining town squares from Maryland's provincial period is more alive than ever today! The Upper Square, also known as the War Memorials Garden, houses a two-sided World War I Memorial with plaques with the names of 27 St. Mary's County residents who fell during the War. Specialty shops and fine-dining restaurants surround the Upper Square of this walkable town, and the Square is the host location of popular events like outdoor concerts, Beach Party on the Square, Christmas on the Square, and other exciting events that draw thousands of visitors to town annually. 

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Check out our Info Guide for planning an event or a group visit in Leonardtown.



Find out what there is to see and do in this eclectic Southern Maryland Town.


Thank you to our generous supporters below. Events and happenings in Leonardtown wouldn't be possible without their kind support.

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