The Town of Leonardtown is ringing in the holiday season on Friday, November 29th 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, face painting, 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 PM!

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 thru 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.
  • The Firehouse Lot and Old Carnival Lot (Shadrick and Lawrence) will not be available for public parking this year as it will be the new location for the petting zoo for the event.


  • 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.
  • NEW – Spectators are encouraged to park at CSM and take advantage of the free shuttle bus service which runs between CSM and the St. Aloysius Church from 4:30 PM – 9:30 PM.  Once the CSM parking lot is full, spectators will be directed to park at the Governmental Center and take the shuttle bus from that location. A wheelchair accessible shuttle will also be available from CSM, and once CSM closes, it will be available from the Governmental Center, courtesy of The Center for Life Enrichment.
  • Handicap parking is also available in Town in the public lot next to the Hair Company and in the lot across from the Executive Inn on Park Avenue. Once these lots are full, spectators will be directed to the CSM or Governmental Center parking.
  • Free 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 signs as well as police and volunteer instructions.

Christmas on the Square is sponsored by the Leonardtown Volunteer Fire Department, the Leonardtown Business Association and the Commissioners of Leonardtown.  For further information, please call 301-475-9791.

(Rain date:  The rain date will consist of the Annual Tree Lighting only on Saturday, November 30, 2019 at 7:00 PM.)