Town Presents Christmas on The Square
The holiday season begins in Leonardtown when Santa arrives for Christmas on the Square and the annual tree lighting in the Town Square on Friday, November 28, 2025. The festivities begin at 4:30pm with holiday music, entertainment, sleigh rides, train rides, hayrides, live nativity, balloon art, face painting, children’s crafts, hot drinks, food, holiday treats, and other fun activities.
Closures and Restrictions:
Downtown Leonardtown Square – including Washington Street and Fenwick Street – will be closed to through traffic and parking from 1 to 10pm.
Courthouse Drive, Guyther Drive, Camalier Drive, and portions of Park Avenue, Shadrick Street, Pope Street, and Church Street will also have extremely restricted access before and during the event.
Residents living around Tudor Hall should enter town via Lawrence Avenue to access their neighborhood, as access to Courthouse Drive will be restricted.
Parking/Shuttles:
Parking can be found at St. Mary’s Ryken High School, the Blackbelt Academy lot on Gregory Drive, and the grass lots on either side of Courthouse Drive near Fenwick Street. Please note: These lots do not have a shuttle service, and you must walk into town. Spectators are encouraged to park at the auxiliary lots at CSM, the governmental center, or the Leonardtown Library/Garvey Senior Center lots.
Note: there is no rain date for the event. In the event of inclement weather, a decision will be made as to whether the event will need to be canceled by 10am Friday, November 28. The decision will be announced on the Town of Leonardtown Facebook Page.
For further information, contact Aris Nazarova at aris.nazarova@leonardtownmd.gov or 301-475-9791.
