Leonardtown Christmas Events

Christmas events Happening Next in Leonardtown, MD

Christmas on the Square & Annual Tree Lighting

 Town of Leonardtown 28 Nov 2025
CHRISTMAS

Small Business Saturday with The Grinch & Cindy Lou Who

 Town Market LLC 29 Nov 2025
SHOPPING

Naughty or Nice DJ Night

 22695 Washington St, Leonardtown, MD 29 Nov 2025
HOLIDAY

Hope In Harmony Winter Concert Series - Noel

 Leonardtown High School 13 Dec 2025
ENTERTAINMENT

Social’s Naughty Santa Party!

 41655 Fenwick St, Leonardtown, MD 20 Dec 2025
PARTIES

St. Maries Choral Arts Home Concert Carol Sing

 First Saints Community Church 15 Dec 2025
CONCERTS

SANTA MINIS “Photos with Santa “2025”

 Starrella Photography by Aprilynn 29 Nov 2025
PICTURES-WITH-SANTA

Fur Babies with the Grinch and Holiday Market

 22675 Washington St, The Bell Bldg Unit 106, Leonardtown MD 6 Dec 2025
HOLIDAY

Come Out and See the Grinch & Christmas Shopping Spree

 Town Market LLC 13 Dec 2025
SHOPPING

Pictures with Santa Clause

Town Market LLC 20 Dec 2025
PICTURES-WITH-SANTA