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Christmas On The Square

The holiday season begins in Leonardtown when Santa arrives for Christmas on the Square & the Annual Tree Lighting Ceremony in the Town Square on Friday, November 29, 2024. The festivities begin at 4:30 PM with holiday music, entertainment, sleigh rides, train rides, hayrides, live nativity, balloon art, face painting, children's crafts, hot drinks, food, holiday treats and other fun activities! This beloved annual event is FREE and open to the public. Please find parking, road closure and more details below. For further information contact: Aris Nazarova at or 301-475-9791.  

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 can be found at St. Mary’s Ryken High School, the Blackbelt Academy lot on Gregory Drive, and the grass lots on either side of Courthouse Drive near Fenwick Street. 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 which runs between CSM, the Governmental Center, the Leonardtown Library/Garvey Senior Center and the Olde Town Pub parking lot from 4:30 PM – 8:30 PM.  Shuttle service for the evening is courtesy of Patuxent Transportation (Note: the Leonardtown Trolley shuttles provided by Patuxent Transportation will only be providing shuttle service, and will not go through the neighborhoods during the evening), International Association of Machinists & Aerospace Workers Winpisinger Education & Technology Center and Carter Bus Service.

  • Handicap parking is also available in Town at the Mattingley Gardiner parking lot on the corner of Fenwick St. and Lawrence Ave. and in the public lot next to the Hair Company on Washington Street. Once these lots are full, spectators will be directed to park in one of the auxiliary lots noted.

  • 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.

  • For event safety, spectators are asked to obey all posted No Parking and Reserved Parking signs as well as police and volunteer instructions.

  • Note: there is no rain date for this event. In the event of inclement weather, a decision will be made as to whether the event will need to be cancelled by 9 a.m. on Friday, November 29, 2024. The decision will be announced on on this page and the Town of Leonardtown Facebook Page.


  • Christmas on the Square is sponsored by the Commissioners of Leonardtown, the Leonardtown Volunteer Fire Department, and the Leonardtown Business Association.

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