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: VisitLeonardtownMD.com/HolidaysinLeonardtown.
Christmas on the Square – Friday, November 26, 2021 – This beloved traditional event takes place the day after Thanksgiving and kicks off the holiday season in Leonardtown when Santa arrives for the annual tree lighting. The festivities begin at 4:30 PM with holiday music, entertainment, horse and carriage rides, sleigh rides, train rides, hayrides, a live nativity, 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. Learn more here>
Small Business Saturday – Saturday, November 27, 2021 – The day after Christmas on the Square, our stores, galleries and shops will be open and ready to help you with your holiday shopping. 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 (Download the Trolley Route Map). For more info call 301-475-9791.
Santa & Mrs. Claus on the Square – Saturday, December 18, 2021 – Bring your wish lists and your cameras for a visit with Santa and Mrs. Claus! This event is FREE and open to the public (no reservations are needed).
Reservations for private Meet-and-Greets with Santa are available for families with loved ones with disabilities & for celebrations of baby’s 1st Christmas. For more information contact: [email protected] or 301-475-9791.
Private Meet-and-Greets with Santa – Tuesday, December 14, 2021 / Saturday, December 18, 2021 – Reservations for private Meet-and-Greets with Santa are available for families with loved ones with disabilities & for families celebrating a baby’s 1st Christmas. These private meetings are a magic experience for families who usually are unable to bring their loved ones to meet Santa in settings with long lines and crowds. Location will be provided upon registration. For more information contact: [email protected] or 301-475-9791
