LEONARDTOWN, MD – The holiday season in Leonardtown will officially kick off on Friday, November 29, 2024, with the annual Christmas on the Square and Tree Lighting Ceremony. This cherished tradition, hosted from 4:30 p.m. to 8:30 p.m., offers festive fun for the whole family, culminating in Santa’s arrival and the lighting of the Christmas tree at 7:00 p.m.
The event features live entertainment, sleigh and fire truck rides, a living nativity, balloon art, a holiday market, and a variety of food options. Organized by the Commissioners of Leonardtown, the Leonardtown Volunteer Fire Department, and the Leonardtown Business Association, this year’s celebration promises a joyful start to the holiday season.
Parking Options and Shuttle Services
Organizers have coordinated with local agencies to ensure smooth parking and transit. Visitors are encouraged to park at designated lots and use the free shuttle service. Shuttles will operate between parking areas and the St. Aloysius Church lot.
Shuttle-Served Parking Locations:
- College of Southern Maryland (CSM)
- Governmental Center
- Leonardtown Library/Garvey Senior Center
Parking Locations Without Shuttle Service:
- St. Mary’s Ryken High School
- Blackbelt Academy lot on Gregory Drive
- Grass lots on Courthouse Drive near Fenwick Street
Handicap Parking:
Accessible parking is available at:
- Mattingley Gardiner Funeral Home (Fenwick St. and Lawrence Ave.)
- Public lot next to the Hair Company (Washington St.)
Access to these spaces requires a valid handicap pass, decal, or license plate.
Road Closures and Restrictions
To accommodate the event, several downtown streets will close or have restricted access:
- Full Closures: Downtown Leonardtown Square, Washington Street, and Fenwick Street (1:00 p.m. – 10:00 p.m.)
- Restricted Access: Portions of Courthouse Drive, Guyther Drive, Camalier Drive, Park Avenue, Shadrick Street, Pope Street, and Church Street.
Residents in the Tudor Hall area should enter via Lawrence Avenue to access their homes during the event.
Weather Contingency Plans
The event does not have a rain date. In the event of inclement weather, a decision will be made and announced by 9:00 a.m. on November 29, 2024. Updates will be posted on VisitLeonardtownMD.com/ChristmasontheSquare and the Town of Leonardtown Facebook page.
Acknowledgments
The event’s success is attributed to the collaborative efforts of Town officials, the St. Mary’s County Sheriff’s Office, Emergency Management Division, Maryland State Police, and numerous local volunteer organizations.
For more information, visit VisitLeonardtownMD.com/ChristmasontheSquare.
