Leonardtown, MD -The Town of Leonardtown is ringing in the holiday season on Friday, November 26th 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, airbrush tattoos, balloon art, a living nativity, 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 at 7:00 p.m.!

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, St. Mary’s County 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 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:

  • Once in-Town parking lots are full, spectators will be directed to auxiliary lots.
  • For cars to exit Town efficiently and safely after Santa’s arrival, the fire truck rides will be shutting down completely at 6:45 PM. Please plan accordingly.
  • Spectators are encouraged to park at CSM or the Governmental Center and take advantage of the free shuttle bus service which runs between CSM, the Governmental 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 the CSM or Governmental Center parking.
  • Parking can also be found at Leonardtown Elementary School and St. Mary’s Ryken High School, in addition to designated lots along Lawrence Avenue, Washington Street and Park Avenue.
  • For event safety, spectators are asked to obey all posted No Parking and Reserved Parking signs as well as police and volunteer instructions.

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.

(Rain date: The rain date will consist of the Annual Tree Lighting only on Saturday, November 27, 2021, at 7:00 PM.)


David M. Higgins II, Publisher/Editor

David M. Higgins was born in Baltimore and grew up in Southern Maryland. He has had a passion for journalism since high school. After spending many years in the Hospitality Industry he began working in...

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