Leonardtown Holiday Events

Christmas on the Square & Annual Tree Lighting

Town of Leonardtown 28 Nov 2025

Small Business Saturday with The Grinch & Cindy Lou Who

Town Market LLC 29 Nov 2025

Naughty or Nice DJ Night

22695 Washington St, Leonardtown, MD 29 Nov 2025

Ugly Sweater Party at The Rex featuring In Too Deep

The Rex Theatre 28 Nov 2025

Winter Market ~ Marie & Nash

22675 Washington St., Leonardtown, MD, United States, Maryland 20650 5 Dec 2025

Wreaths & Wine Dec 6th

23190 Newtowne Neck Rd, Leonardtown, MD, United States, Maryland 20650 6 Dec 2025

Hope In Harmony Winter Concert Series - Noel

Leonardtown High School 13 Dec 2025

Wreaths & Wine Nov

23190 Newtowne Neck Rd, Leonardtown, MD, United States, Maryland 20650 29 Nov 2025

Baked & Boozy: Baked Goods Sip & Shop

22695 Washington St, Leonardtown, MD 7 Dec 2025

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

Shepherd's Old Field Market 7 Dec 2025

Thanksgiving center piece workshop

22720 Duke street, Leonardtown, MD 22 Nov 2025

MTC Holiday Meet-Up | Leonardtown Scavenger Hunt

The Inn at Leonardtown 16 Dec 2025

Tinsel and Tape: Holiday Wrapping Workshop

The Fenwick Inn 11 Dec 2025

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

Shepherd's Old Field Market 14 Dec 2025

St. Maries Choral Arts Home Concert Carol Sing

First Saints Community Church 15 Dec 2025

Holiday Dressage Schooling Show 🎄

41345 Camp Maria Rd, Leonardtown, MD 20650-4220, United States, Leonardtown, MD 13 Dec 2025

Holiday Shoppe

41695 Fenwick Street, Leonardtown, MD 22 Nov 2025

Fur Babies with the Grinch and Holiday Market

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

Come Out and See the Grinch & Christmas Shopping Spree

Town Market LLC 13 Dec 2025

Pictures with Santa Clause

Town Market LLC 20 Dec 2025

Holiday Market with The Grinch & Cindy Lou Who

Town Market LLC 28 Nov 2025