Happening Next

Leonardtown Holiday Events

Holiday 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

FOLs Fall BOOK Sale - Bigger & Better!

 42455 Fairgrounds Rd, Leonardtown, MD 20650, United States 7 Nov 2026

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
CHRISTMAS-MARKETS-AND-FAIRS

Holiday Market with The Grinch & Cindy Lou Who

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

BAF Holiday Dressage Schooling Show

 41345 Camp Maria Rd, Leonardtown, MD 20650-4220, United States, Leonardtown, MD 12 Dec 2026
HOLIDAY