Leonardtown Parties Events

Small Business Saturday with The Grinch & Cindy Lou Who

Town Market LLC 29 Nov 2025

Hit or Miss Halloween!!

22695 Washington St, Leonardtown, MD 31 Oct 2025

Paint Your Pet's Portrait Fundraiser

Wine & Design (Leonardtown, MD) 14 Nov 2025

Social’s Slasher Night!

41655 Fenwick St, Leonardtown, MD 25 Oct 2025

Easter Extravaganza

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

Monster Mash Bash

Leonardtown Wharf 19 Oct 2025

Christmas on the Square & Annual Tree Lighting

Town of Leonardtown 28 Nov 2025

Death at the Disco

Antoinette’s Garden 19 Oct 2025

FOL's Fall 2025 BOOK Sale

23630 Hayden Farm Ln, Leonardtown, MD 20650-5888, United States 8 Nov 2025

Levi Stephens LIVE

22845 Washington Street. Unit C, Leonardtown, MD 18 Oct 2025

Social’s Storybook Horror Event!

41655 Fenwick St, Leonardtown, MD 31 Oct 2025

Chesapeake Mermaid at U.S. Oyster Festival

St. Mary's County Fairgrounds 18 Oct 2025

Social’s Naughty Santa Party!

41655 Fenwick St, Leonardtown, MD 20 Dec 2025

Socials Saturday Night Lights Event

41655 Fenwick St, Leonardtown, MD 22 Nov 2025

Holiday Kickoff at the Marketplace

23976 Point Lookout Rd, Leonardtown, MD, United States, Maryland 20650 8 Nov 2025

Cars & Coffee Car Show

22675 Washington Street, The Bell Bldg Unit 106, Leonardtown, MD 19 Oct 2025

Acoustic Wildgood

Port of Leonardtown Winery 8 Nov 2025

Cars & Coffee Car Show

22675 MD-326, Leonardtown, MD 20650-3848, United States 18 Oct 2025

Valentines' Day Sweets & Treats

Town Market LLC 14 Feb 2026

Cars & Coffee Car Show

22675 MD-326, Leonardtown, MD 20650-3848, United States 19 Oct 2025

Fur Babies with the Grinch and Holiday Market

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

Eclipse at The Rex

The Rex 15 Nov 2025