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

Socials Saturday Night Lights Event

41655 Fenwick St, Leonardtown, MD 22 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

First Saturday of the Month Market Series

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

Winter Market ~ Marie & Nash

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

Sip, Stroll & Sniff

Shepherd's Old Field Market 22 Nov 2025

Soothe Session

22660 Washington St 29 Nov 2025

Baked & Boozy: Baked Goods Sip & Shop

22695 Washington St, Leonardtown, MD 7 Dec 2025

Wreaths & Wine Dec 6th

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

Easter Extravaganza

Town Market LLC 22675 Washington Street, The Bell Bldg Unit 106, Leonardown MD 28 Mar 2026

Hope In Harmony Winter Concert Series - Noel

Leonardtown High School 13 Dec 2025

Social’s Naughty Santa Party!

41655 Fenwick St, Leonardtown, MD 20 Dec 2025

2ND ANNUAL DRINKSGIVING DECADES PARTY!

The Rex Theatre 26 Nov 2025

Nicotine Cessation Class - Standalone Sessions

21580 Peabody St, Leonardtown, MD, United States, Maryland 20650 19 Nov 2025

Hawthorne Heights in Leonardtown

The Rex 20 Nov 2025

Fall Floral pumpkin centerpiece workshop

23190 Newtowne Neck Rd, Leonardtown, MD, United States, Maryland 20650 22 Nov 2025

Sound bath Journey

22660 Washington St 27 Dec 2025

Wreaths & Wine Nov

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