Leonardtown kicks off the holiday season with Christmas on the Square and the Annual Tree Lighting Ceremony November 28, 2025, from 4:30 p.m. to 8:30 p.m. in the downtown square.
The free community event features live entertainment, sleigh and fire truck rides, balloon art, a living nativity scene, a holiday market, food vendors, and additional activities. Santa arrives ahead of the tree lighting at 7 p.m., performed by the Leonardtown Volunteer Fire Department.
Organizers coordinate with the St. Mary’s County Sheriff’s Office, Maryland State Police, local fire and rescue squads, and other agencies to manage crowds and ensure safety during the gathering, which draws thousands to the historic town center.
Downtown Leonardtown Square, including Washington and Fenwick streets, closes to through traffic and parking from 1 p.m. to 9 p.m. Additional restrictions affect Courthouse Drive, Guyther Drive, Camalier Drive, and parts of Park Avenue, Shadrick Street, Pope Street, and Church Street. Residents near Tudor Hall access homes via Lawrence Avenue.
Attendees receive encouragement to use remote parking and free shuttle service. Shuttles operate from the College of Southern Maryland Leonardtown campus, St. Mary’s County Governmental Center, and Leonardtown Library/Garvey Senior Center, with drop-off and pickup at St. Aloysius Church lot in downtown.
Walk-in parking options include St. Mary’s Ryken High School, Blackbelt Academy lot on Gregory Drive, and grass lots along Courthouse Drive near Fenwick Street, without shuttle access.
Handicap-accessible spaces locate at Mattingley Gardiner Funeral Home lot on Fenwick Street and Lawrence Avenue, and the public lot beside the Hair Company on Washington Street. Access enters through Lawrence Avenue, requiring a valid handicap placard, plate, or pass for direction by personnel.
No rain date exists for the event. Officials decide on cancellation for inclement weather by 10 a.m. November 28, 2025, posting updates on the event page and town social media.
Past iterations included train rides, face painting, kettle corn, and petting zoos in some years, varying by organizer availability. The tree, typically a large evergreen placed centrally, remains lit through the season, complementing decorations at shops, wineries, and the wharf along Breton Bay.
For those arriving early, downtown businesses often extend hours, offering dining and shopping amid the setup. The Leonardtown Volunteer Fire Department traditionally handles the lighting switch, tying into their role in community parades and emergencies.
Updates on weather or changes post on the official Visit Leonardtown site, which also archives photos and schedules from prior years.
