For these Exciting 2021 Events


Beach Party
on the Square

We regretfully announce that this event has been cancelled due to COVID-19 restrictions. 


Veterans Day Parade / Memorial Wreath Laying Ceremony

Wednesday, November 11th

10:00 a.m. - 1:00 p.m.
A celebration of the brave men and women who have served our Country.
Learn More>

Santa & Mrs. Claus on the 'Square

Saturday, December 12th

11:00 a.m. - 1:00 p.m.
Bring your cameras and wish lists and visit with the jolly old elf and his lovely wife.
Learn More>



First Friday's

Year Round

Join us year-round every First Friday of the month from
5:00 p.m. to 8:00 pm for an evening of fun entertainment, unique shopping and various
dining options!
Learn More>


Trick-or-Treat on the Square

Saturday, October 24th

3:00 p.m. - 5:00 p.m.
Trick-or-Treat with local businesses around Historic Leonardtown Square.
Learn More>


Santa & Mrs. Claus on the Square

Saturday, December 12th 
11:00 a.m. - 1:00 p.m.
The holiday season officially begins with the annual holiday celebration in Historic Leonardtown Square featuring live music and dance, rides, food and Santa's arrival to light the tree.
Learn More>


Meet-and-Greets with Santa

Saturday, December 12th & Tuesday, December 15th

Reservations for private meetings with Santa are available for families with loved ones with disabilities and for families celebrating a baby's first Christmas. Learn More>

Summer Music Festival_2C.jpg

Leonardtown Summer Music Festival

Saturday, June 28th -
Sunday, August 23rd

FREE, live concerts, dancing, raffles prizes and more in historic Leonardtown Square. Learn More>

  • Town of Leonardtown
  • Town of Leonardtown
  • YouTube - Leonardtown Maryland

This Website is Sponsored
and Maintained by:

Join our mailing list

Leonardtown Business Association
PO Box 2541
Leonardtown, MD 20650

© 2019 by the Leonardtown Business Association

  • Facebook Basic Black