Christmas Decorations

Leonardtown for the Holidays


Come to Leonardtown for the Holidays! The holiday season officially begins at Christmas on the Square when Santa arrives for the Annual Tree Lighting Thanksgiving Weekend on Friday, November 26, 2021 and continues with Small Business Saturday the next day on Saturday, November 27, 2021. There's so much to do throughout Leonardtown for the holidays from fine dining, shopping, arts & entertainment, exciting events, activities and more!  Here's just a highlight of some holiday fun you can find here in Leonardtown for the holidays (below)!


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.



This is an important message for attendees of the Christmas on the Square & Annual Tree Lighting event being held Friday, November 26th, from 4:30-8:30 p.m. in Leonardtown. In light of recent events around the Country we are unable to offer open parking in the downtown area to visitors. Plenty of parking will be available at the College of Southern Maryland, the Governmental Center and St. Mary’s Ryken High School parking lots for event attendees with multiple shuttles running continuously throughout the event. Only visitors with handicap parking placards, persons with reservations to businesses with private parking, St. Aloysius mass attendees or volunteers can access Lawrence Avenue. There will be no access from Rt. 5 onto Washington Street. Only residents, performers and volunteers will have access from Fenwick Street to Courthouse Drive. Thank you for your cooperation in making this a safe and fun family event. For more info visit: Christmas on the Square

Learn more here>

Gift Shop

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

Santa and Mrs. Claus

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).


Santa & Mrs. Claus on the Square, scheduled for Saturday, December 18, 2021, has been moved inside Ye Olde Towne Cafe (located at: 22685 Washington St, Leonardtown, MD 20650). Bring your wish lists and cameras and join us in welcoming Santa & Mrs. Claus back to Leonardtown! This event is free and open to the public. No reservations are needed. The restaurant will also be open for anyone who wishes to dine before or after their photos with the jolly old elf and his lovely wife.

Please note: If the event is held inside Ye Olde Towne Cafe, you will need to check at the front of the restaurant, get a number and provide your cell phone number. You are welcome to dine while you wait or visit some of our neighboring shops, and we'll give you a call when your turn is coming up. We will announce if the event will be moving indoors on the Town of Leonardtown Facebook page, on the event page and here on this page on the day of the event at around 9 a.m. We look forward to seeing you there!

For more information contact: or 301-475-9791.

Meet and Greet with Santa 1

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. Note: Both Meet-and-Greet events are now full. To be added to the waiting list in the event of cancellation, please contact:

Click on a link below to learn more about Leonardtown for the holidays!

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