Leonardtown Arts & Entertainment District     |     Visit Historic Leonardtown     |     First Fridays In Leonardtown  

On September 14, 2023 Governor Wes Moore announced that Leonardtown in St. Mary’s County is the newest community to receive a Main Street Maryland designation.

Leonardtown is the first designated Main Street in St. Mary’s County, and is home to Southern Maryland’s only designated Arts & Entertainment district. It joins 33 other cities that offer an authentic Maryland experience.  Read more...  

Leonardtown hosts many exciting events throughout the year from concerts and festivals to parades and more that draw thousands of visitors to Town each year.   The Town also hosts many beloved holiday celebrations and events from the Annual Veterans Day Parade & Memorial Ceremony (traditionally the largest parade in Maryland) to the Christmas on the Square & Annual Tree Lighting Ceremony (the official kickoff to the holiday season in Leonardtown).  Check back often and don’t miss a minute of the fun!  

Featured Events     |     Events Calendar

Interested in learning more about the Main Street approach? Visit the below sites!

The Main Street Approach - The Main Street Approach is a time-tested framework for community-driven, comprehensive revitalization.

Main Street Maryland - Discover historic architecture, arts & culture, and unique heritage of our Main Streets.   Explore. Experience. Enjoy!

Main Street Advisory Council CLOSED Session April 2024

Follow Leonardtown Main Street on Instagram
for “Where to Park Wednesdays,” business highlights, event coverage, and more!

   Official Town of Leonardtown Website