Leonardtown, MD – 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 Town Square will be open and decorated for your holiday pleasure. Then don’t miss Santa’s arrival at 7:00 p.m. to light the Christmas Tree in Leonardtown Square. There’s no greater way to experience that holiday magic than being here in Leonardtown for that special moment!

Then return to Leonardtown on Saturday when our stores, galleries and shops will be open and ready to help you with your holiday shopping for Small Business Saturday. Enjoy the friendly, small-town charm that Leonardtown has to offer. Browse our specialty shops and find one-of-a-kind gifts for everyone on your list. Gift cards are also available for dining, shopping or a special experience in Town. 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: VisitLeonardtownMD.com/HolidaysinLeonardtown.

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