Happening Next

Leonardtown Kids Events

Kids Events Happening Next in Leonardtown, MD

Christmas on the Square & Annual Tree Lighting

 Town of Leonardtown 27 Nov 2026
HOLIDAY

Home for The Holidays - A New St. Mary's County Holiday Tradition

 Saint Mary's Fairgrounds 5 Dec 2026
FITNESS USD 0 TO 8

The Old Jail Museum Open for Leonardtown First Fridays (Extended Hours) (FREE)

 41625 Courthouse Dr, Leonardtown, MD, United States, Maryland 20650 4 Sep 2026
ART

Photos with Santa! (Pet **all species** and kid friendly)w

 Balanced Paws Pet Care 13 Dec 2026
NONPROFIT

Small Business Saturday with The Grinch & Cindy Lou Who

 Town Market LLC 28 Nov 2026
DANCE

Holiday Market with The Grinch & Cindy Lou Who

 Town Market LLC 27 Nov 2026
CHRISTMAS-MARKETS-AND-FAIRS

Letters to Santa

 22675 Washington Street, The Bell Bldg Unit 106, Leonardtown, MD, United States, Maryland 20650 27 Nov 2026