Ring in the holiday season on Friday, November 28th from 5 – 9:00 PM with Leonardtown’s annual “Christmas on the Square” and “Annual Tree Lighting Ceremony” held on Washington Street in the Leonardtown Square. 

Event activities start at 5:00 p.m. and include holiday music, rides, an ice sculpture demonstration, a petting zoo, live nativity, face painting, and much more!   Stage performances include Bella Music School, St. Mary’s Ryken Choir, Emma Raphael, The House of Dance, Leonardtown Wildcats Cheerleaders, St. Marie’s Musica and a return visit from Gracie’s Guys and Gals Dance Troupe!  Let the music put you in the holiday mood as you browse the downtown merchants and art galleries that will remain open for your Christmas shopping needs. 

You’ll also want to stop by the Winegardner Auto Showroom Christmas Festival sponsored by the Leonardtown Volunteer Rescue Squad Auxiliary.  See the decorated trees and wreaths, admire the electric train display, sign up for the silent auction, or buy a chance to win a wagon full of toys worth over $500!  There will also be face-painting and grab bags for the kids.  Want other ways to give back this holiday season?  Bring a new, unwrapped toy to donate to Toys for Tots through Winegardner Automotive, or support local charity fundraisers and raffles located around the Square.    

Just outside of the Winegardner showroom, board one of the many rides and travel around the Historical Part of Town, including Tudor Hall, The Old Jail Museum and the Historic Courthouse Building.  Enjoy time away from the crowds with luminaries, Christmas carolers and live-action vignettes.  Boy scouts, churches or other organizations interested in caroling at the event should contact Maria Fleming at maria.fleming2@verizon.net.

Make your way to the Square promptly at 7:00 PM for Santa’s arrival and the lighting of the Town Christmas Tree!  After the tree lighting, stay for a visit with Santa, take the kids for a fire truck ride, or head over to Mrs. Claus’ tent for stories and crafts.  The live holiday entertainment continues with local dancers on the stage and a concert with professional jazz musicians, pianist Joe Holt and vocalist Beth McDonald, at Leonardtown Church of the Nazarene.

Several streets in the downtown Leonardtown Square area will be closed to thru traffic from 3:00 PM – 10:00 PM.  Spectators are encouraged to park at the College of Southern Maryland and take the free shuttle bus service to the Leonardtown Square, or park at Leonardtown Elementary School, St. Mary’s Ryken High School, or other designated lots around Town and enjoy the beautifully decorated walk into Town Square! 

Christmas on the Square is sponsored by the Leonardtown Volunteer Fire Department, the Leonardtown Business Association and the Commissioners of Leonardtown, with gratitude to their community financial partners:  Two Guys Auto Body, Winegardner Automotive, Quality Built Homes, MedStar St. Mary’s Hospital, Marrick Homes, PNC Bank, Burris’ Olde Towne Insurance, and the College of Southern Maryland.  For further information, visit www.leonardtown.somd.com or call 301-475-9791.  (Rain date:  The rain date will consist of the Annual Tree Lighting only on Saturday, November 29, 2014 at 7:00 PM.)Â