Upcoming Event

Christmas on the Square @ Town of Leonardtown

Name: Christmas on the Square and Annual Tree Lighting in Leonardtown, MD
Start: 2026-11-27T16:30:00-05:00
End: 2026-11-27T20:30:00-05:00
Location: Christmas on the Square and Annual Tree Lighting in Leonardtown, MD

Nov 27

Admission: Free
Location: Leonardtown Square
Time:
4:30 PM to 8:30 PM

The holiday season begins in Leonardtown when Santa arrives for the annual Christmas Tree Lighting in the Town Square. The festivities begin at 4:30 PM with holiday music, entertainment, horse and carriage rides, sleigh rides, train rides, hayrides, live nativity, petting zoo, face painting, children’s crafts, hot drinks, fresh kettle corn and other fun activities! Many downtown restaurants and shops around the Town Square will be open and decorated for your holiday pleasure.