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 24, 2023. The festivities begin at 4:30 PM with holiday music, entertainment, sleigh rides, train rides, hayrides, live nativity, petting zoo, face painting, children's crafts, hot drinks, food, holiday treats and other fun activities! (Raindate: Saturday November 25th - Tree Lighting only at 7:30 PM). For more information contact: brandy.blackstone@leonardtownmd.gov or 301-475-9791.