LEONARDTOWN, Md. — Santa’s arrival will kick off Leonardtown’s Christmas on the Square and the annual tree lighting on Friday, Nov. 28, 2025, in the Town Square.
Festivities begin at 4:30 p.m. with holiday music and entertainment, sleigh, train and hayrides, a live nativity, balloon art, face painting, children’s crafts, hot drinks, food, and treats. The event is free and open to the public.
Santa’s entrance and tree lighting, assisted by the Leonardtown Volunteer Fire Department, have become hallmark moments of the celebration, drawing families for rides, live entertainment and a bustling holiday market downtown. A 2024 BayNet photo recap captured the excitement as the fire department led the countdown and the square came alive with lights and cheers.
Right after the tree lighting, the party kicks off at The Rex—when the last carols fade and the Square is glowing, follow the guitars and laughter down Fenwick Street. The bar will be pouring festive cocktails, local craft brews, and seasonal specials like spiked hot chocolate and peppermint martinis. The dance floor will be open, the lights low, and the energy high as In Too Deep tears into 90s/2000s favorites with a holiday twist. Grab your crew, flaunt those gloriously awful sweaters, and snap pics under the neon marquee—this is Leonardtown’s holiday after-party you won’t want to miss. Stay late, sing loud, and let’s make this a hometown tradition that rocks as hard as it shines. The Rex event is 21+, and admission is free!
For information, contact Aris Nazarova at aris.nazarova@leonardtownmd.gov or 301-475-9791.
Road closures and access
Town Square, including Washington Street and Fenwick Street, will be closed to through traffic and parking from 1 to 10 p.m. Courthouse Drive, Guyther Drive, Camalier Drive, and portions of Park Avenue, Shadrick Street, Pope Street, and Church Street will have restricted access. Residents near Tudor Hall should enter town via Lawrence Avenue; access to Courthouse Drive will be limited.
Parking and shuttles
Parking will be available at St. Mary’s Ryken High School, the Blackbelt Academy lot on Gregory Drive, and grass lots along Courthouse Drive near Fenwick Street. These locations do not have shuttle service.
Free shuttle buses will run from 4:15 to 9 p.m. between the College of Southern Maryland (CSM), the St. Mary’s County Governmental Center, and the Leonardtown Library/Garvey Senior Center, with drop-off and pick-up at St. Aloysius Church in downtown Leonardtown. Riders should look for red “Shuttle Pick Up” signs at each location.
• Governmental Center: Access from Baldrige Drive or Leonard Hall Drive; stop is across from the Carter Building.
• Leonardtown Library/Garvey Senior Center: From Hollywood Road, use Leonard’s Grant Parkway, then Hayden Farm Lane; pickup is at the front of the building.
• CSM: The stop is at the back of the campus.
ADA parking will be available at Mattingley-Gardiner Funeral Home (Fenwick St. and Lawrence Ave.) and in the public lot next to The Hair Company on Washington Street (enter via Lawrence Ave., then Shadrick St.). Once full, drivers will be directed to auxiliary lots.
To ease post-ceremony traffic, fire truck rides will stop at 6:45 p.m.
Attendees are asked to follow posted No Parking and Reserved Parking signs and comply with directions from police and volunteers.
Weather plan
There is no rain date. In case of inclement weather, officials will decide by 10 a.m. Friday, Nov. 28, and announce the status on the event page and the Town of Leonardtown Facebook page.
Sponsors
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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