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 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 korn and other fun activities!  If you would like to be a vendor for this year's event, please download the Vendor Application and submit it to brandy.blackstone@leonardtownmd.govFor more information, please call 301-475-9791 or email

Download: Vendor Application