Leonardtown, MD -The Town of Leonardtown is ringing in the holiday season on Friday, November 25th, from 4:30 PM – 8:30 PM with the traditional “Christmas on the Square and Annual Tree Lighting Ceremony.”  Event activities start at 4:30 PM and include live entertainment, rides, balloon art, a living nativity, a petting zoo, food, and much more!  

Come early, so you have time to park and make your way to the Square to enjoy all the exciting activities, and don’t miss Santa’s arrival and the lighting of the Town Christmas Tree a 7:00 PM by the Leonardtown Volunteer Fire Department.

Thanks to the cooperative efforts of Town officials, 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, Fire and Rescue Chiefs, the Leonardtown Volunteer Fire Department, and other local volunteer fire departments and rescue squads, plans are in place for increased safety and security.  Please note the following measures that will be in effect for this year’s event:

Closures and Restrictions:

  • Downtown Leonardtown Square – including Washington Street and Fenwick Street – will be closed to through traffic from 2:00 PM – 10:00 PM
  • Courthouse Drive, Guyther Drive, Camalier Drive, and portions of Park Avenue, Shadrick Street, Pope Street, and Church Street will also have restricted access before and during the event.
  • Residents around Tudor Hall should enter Town via Lawrence Avenue to access their neighborhood, as Courthouse Drive will be restricted.


  • Parking can be found at Leonardtown Elementary School and St. Mary’s Ryken High School. Once the parking lots are full, spectators will be directed to park at the auxiliary lots at CSM, the Governmental Center, or the Leonardtown Library/Garvey Senior Center Lots.
  • Spectators are encouraged to park at the auxiliary lots noted above and take advantage of the free shuttle bus service between CSM, the Governmental Center, the Leonardtown Library/Garvey Senior Center, and St. Aloysius Church from 4:30 PM – 9:30 PM.  Shuttle service for the evening is courtesy of Patuxent Transportation, International Association of Machinists & Aerospace Workers Winpisinger Education & Technology Center, and Carter Bus Service.
  • Handicap parking is also available in Town in the public lot next to the Hair Company. Once this lot is full, spectators will be directed to park in one of the lots noted.
  • For cars to exit Town efficiently and safely after Santa’s arrival, the fire truck rides will shut down completely at 6:45 PM. Please plan accordingly.
  • For event safety, spectators are asked to obey all posted No Parking and Reserved Parking signs and police and volunteer instructions.

Inclement Weather Plan:

Due to forecasted inclement weather conditions, a decision about whether to cancel Christmas on the Square will be made. A notification will be posted no later than Tuesday, November 22, 2022, at 3 p.m.

It will be announced at: VisitLeonardtownMD.com/ChristmasontheSquare and facebook.com/TownofLeonardtown. Rain date: The rain date will consist of the Annual Tree Lighting only on Saturday, November 26, 2022 at 7:00 p.m.

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