Leonardtown, MD -The Town of Leonardtown is ringing in the holiday season on Friday, November 28th from 4:30pm – 8:30pm with the beloved Christmas on the Square and Annual Tree Lighting Ceremony. Event festivities start at 4:30pm and include live entertainment, sleigh & fire truck rides, balloon art, a living nativity, a holiday market, food and much more! You won’t want to miss Santa’s arrival and the lighting of the Christmas Tree at 7:00pm by the Leonardtown Volunteer Fire Department!
Thanks to the cooperative efforts of Town officials
& staff, the St. Mary’s County Sheriff’s Office, the St. Mary’s County
Emergency Management Division, Maryland State Police, Maryland State Highway, St.
Mary’s County Public Works, Leonardtown Volunteer Fire Department, Leonardtown
Volunteer Rescue Squad and other local volunteer fire departments and rescue
squads, plans are in place for increased safety and security.
Parking
Information
· Spectators are
encouraged to park at CSM, the Governmental Center, and the Leonardtown
Library/Garvey Senior Center and take advantage of the free shuttle service that
drops off /picks up at St. Aloysuis Church parking lot.
· Additional
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. These lots do not have shuttle service and attendees must walk
to the downtown area.
· Handicap parking
is available in Town at the Mattingley Gardiner Funeral Home parking lot on the
corner of Fenwick St. and Lawrence Ave. and in the public lot next to the Hair
Company on Washington Street. To access these lots, enter via Lawrence Ave. and
you will be directed to these lots (handicap decal/pass/license plate
required).
Closures
and Restrictions:
· Downtown Leonardtown Square – including Washington Street and Fenwick Street – will be closed to through traffic from 1:00pm – 9:00pm.
· 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.
There is no rain date for the event. In the event of
inclement weather, a decision will be by 9:00am on Friday, November 28, 2025.
The decision will be announced on VisitLeonardtownMD.com/ChristmasontheSquare and the Town of Leonardtown Facebook page.
Christmas on the Square is sponsored by the Commissioners of
Leonardtown, the Leonardtown Volunteer Fire Department, and the Leonardtown
Business Association. For further
information, please visit: VisitLeonardtownMD.com/ChristmasontheSquare.