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FEATURED EVENTS

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Leonardtown hosts many exciting events throughout the year from concerts and festivals to parades and more that draw thousands of visitors to Town each year. Plans for the 2023 event season are underway. Please check the list of 2023 Town events below and mark your calendars. Check this page often for updates and the latest news about upcoming events and activities in Leonardtown. For more information, please call 301-475-9791 or email brandy.blackstone@leonardtownmd.gov.

festivals

Festivals, Ongoing & Special Events

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Moll Dyer Day Weekend

February 24 - 26, 2023
2021 evens

SIGNATURE HOLIDAY EVENTS

The Town of Leonardtown is hosts many beloved holiday celebrations and events from the Annual Veterans Day Parade & Memorial Ceremony (traditionally the largest parade in Maryland) to the Christmas on the Square & Annual Tree Lighting Ceremony (the official kickoff to the holiday season in Leonardtown). View the upcoming Signature Holiday Events below. Please check this page often for updates, view a full list of events throughout Leonardtown in the Event Calendar, or contact brandy.blackstone@leonardtownmd.gov to be added to the Events & Happenings Mailing List so you don't miss a minute of the fun.

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THE HALLOWEEN MOVIE FEST AT THE WHARF


SATURDAY, OCTOBER 21, 2023 AT 5 PM - 8:30 PM

Ghost and ghouls, ninjas and ballerinas join us for an exciting evening of Halloween fun at the Leonardtown Wharf when the Town of Leonardtown Presents The Leonardtown Halloween Movie Festival in the Park on Saturday, October 21st from 5 p.m. - 8:30 p.m. We'll be screening a popular Halloween favorite (TBA)!

 

This event is FREE, and open to the public, but spacing/parking is limited on a first come, first serve basis. Please bring a blanket or lawn chair for your comfort.

For more information contact: brandy.blackstone@leonardtownmd.gov or 301-475-9791. 

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VETERANS DAY PARADE AND WREATH LAYING MEMORIAL CEREMONY 


Saturday, November 11, 2023 AT 10 AM - 1 PM
The Commissioners of St.Mary’s County and the Commissioners of Leonardtown invite the public to salute America’s Veterans at the Annual Veterans Day Parade in Leonardtown! The parade steps off from St. Mary’s Ryken High School, proceeds through Town Square and is immediately followed by a Memorial Ceremony. For more information contact: brandy.blackstone@leonardtownmd.gov
or 301-475-9791. 

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CHRISTMAS ON THE SQUARE 
 


FRIDAY, NOVEMBER 24, 2023 AT 4:30 PM - 8:00 PM
The holiday season begins in Leonardtown
when Santa arrives for the annual Christmas Tree Lighting in the town Square. The festivities begin at 4:30 PM with holiday music, entertainment, sleigh rides, train rides, hayrides, live nativity, petting zoo, face painting, children's crafts, hot drinks, food, holiday treats and other fun activities! (Raindate: Saturday November
25th - Tree Lighting only at 7:30 PM). Please note time change.
For more information contact: brandy.blackstone@leonardtownmd.gov
or 301-475-9791.  

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TUESDAY MEET-AND-GREET WITH SANTA 

TUESDAY, DECEMBER 12, 2023 AT 4 PM - 6 PM
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. The Tuesday Meet-and-Greet is being held on Tuesday, December 12, 2023 from 4 PM - 6 PM. Location will be provided upon registration. For more information contact: brandy.blackstone@leonardtownmd.gov or 301-475-9791. 

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SATURDAY MEET-AND-GREET WITH SANTA 

SATURDAY, DECEMBER 16, 2023 AT
9:30 AM- 10:30 AM

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. Location will be provided upon registration. For more information contact: brandy.blackstone@leonardtownmd.gov
or 301-475-9791. 

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SANTA & MRS. CLAUS ON THE SQUARE (TENTATIVE)

SATURDAY, DECEMBER 16, 2022 AT
11 AM - 1 PM

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: brandy.blackstone@leonardtownmd.gov
or 301-475-9791. 

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