Christmas On The Square

Christmas on the Square is a time honored tradition in Leonardtown. The holiday season officially begins when Santa arrives for the annual Christmas Tree Lighting in the Town Square. We are happy to announce that we are planning a live event for this year, scheduled to take place on Friday, November 26, 2021 on Thanksgiving Weekend in Leonardtown Square. This year's festivities (sponsored once again by the Commissioners of Leonardtown and the Leonardtown Volunteer Fire Department) begin at 4:30 PM with holiday music, entertainment, horse and carriage rides, sleigh rides, train rides, hayrides, a live nativity, airbrush tattoos, balloon art, children’s crafts, hot drinks, food and other fun activities! Please find the event map and details regarding the road closure, parking and inclement weather plan below. For more information, please call 301-475-9791 or email



IMPORTANT UPDATE REGARDING THIS YEAR'S EVENT: This is an important message for attendees of the Christmas on the Square event being held Friday, November 26th, from 4:30-8:30 p.m. in Leonardtown. In light of recent events around the country we are unable to offer open parking in the downtown area to visitors. Plenty of parking will be available at the College of Southern Maryland, the Governmental Center and St. Mary’s Ryken High School parking lots for event attendees with multiple shuttles running continuously throughout the event. Only visitors with handicap parking placards, persons with reservations to businesses with private parking, St. Aloysius mass attendees or volunteers can access Lawrence Avenue.  There will be no access from Rt. 5 onto Washington Street. Only residents, performers and volunteers will have access from Fenwick Street to Courthouse Drive. Thank you for your cooperation in making this a safe and fun family event. See the event map followed by more details on the parking/shuttle stops below.

Christmas on the Square Event Map:


Download: Event Map & Map Key

Event Details:



  • Spectators are encouraged to park at CSM, the Governmental Center or St. Mary's Ryken High School and take advantage of the free shuttle bus service which runs between CSM, the Governmental Center, and Ryken High School (new this year) 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 and in the gravel lot on Lawrence Avenue across from Fenwick Street. Once these lots are full, handicap motorists will also be directed to park at CSM, the Governmental Center or St. Mary's Ryken High School and catch the free shuttles into Town.

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

Inclement Weather Plan:

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

  • A decision about whether to cancel the event will be made by 12 p.m. and posted here on this page and on the Town of Leonardtown Facebook page.

2021 Christmas on the Square Map-11.22.21.png