Happening Next

Leonardtown Holiday Events

Holiday events Happening Next in Leonardtown, MD

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

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

Small Business Saturday with The Grinch & Cindy Lou Who

 Town Market LLC 28 Nov 2026
DANCE

Fur Babies with the Grinch and Holiday Market

 22675 Washington St, The Bell Bldg Unit 106, Leonardtown MD 5 Dec 2026
HOLIDAY

Holiday Market with The Grinch & Cindy Lou Who

 Town Market LLC 27 Nov 2026
HOLIDAY

Arts & Entertainment Celebration First Friday

 22699 MD-326, Leonardtown, MD 20650-3848, United States 5 Sep 2026
FIRST-FRIDAY