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Leonardtown Holiday Events in November and December 2021

The holiday season begins in Leonardtown on Thanksgiving weekend. The festivities kick off with Christmas on the Square on Friday, November 26, 2021. Enjoy live holiday music, entertainment, horse and carriage rides, sleigh rides, train rides, a live nativity, a petting zoo, airbrush tattoos, balloon art, children’s crafts, hot drinks, food and fun activities! Many downtown restaurants and shops around the Town Square will be open and decorated for your holiday pleasure. Then don’t miss Santa’s arrival at 7:00 p.m.! for the Christmas Tree Lighting in Leonardtown Square. There’s no greater way to experience that holiday magic than being here in Leonardtown for that special moment! Drop the kids off at Above Par Golf while you shop and dine to your hearts content. The kids will enjoy exciting golfing/gaming activities while you have a relaxing afternoon to yourself or even a visit with friends. The Leonardtown Trolley will be offering free rides from 11 a.m. – 5 p.m. to make it easy to get around to all the shopping and fun activities throughout Leonardtown. For more information visit: Christmas on the Square – Friday, November 26, 2021 – This beloved traditional event takes place the day after Thanksgiving and […]

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