CANCELLED 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>
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>
Leonardtown Summer Music Festival
Saturday, June 28th -
Sunday, August 23rd
FREE, live concerts, dancing, raffles prizes and more in historic Leonardtown Square. Learn More>