Upcoming Events in Leonardtown

Vendors of Southern MD

 Town Market LLC 20 Sep 2025
SPORTS

Outdoor Movie Night in LTown Alley

 LTown Alley (Alice in LTown Mural) - 41676 Park Ave, Leonardtown, MD 20650, United States 26 Sep 2025
ENTERTAINMENT

Blessing of the Fleet 2025

 Leonardtown Wharf 4 Oct 2025
FIREWORKS

Hinder at The Rex (Leonardtown, MD)

22695 Washington St, Leonardtown, MD 20650 19 Sep 2025
ART

Small Business Saturday with The Grinch & Cindy Lou Who

 Town Market LLC 29 Nov 2025
SHOPPING

Puppet Show in the Park

 Port of Leonardtown Park & Kayak Launch 20 Sep 2025
ART

Salsa on the Vine September

 23190 Newtowne Neck Rd, Leonardtown, MD, United States, Maryland 20650 19 Sep 2025
ENTERTAINMENT

Wine & Whiff

 21935 Society Hill Rd , Leonardtown, MD, United States, Maryland 20650 13 Sep 2025
SPORTS

Sip ‘n Swap Book Club

 41655 Fenwick St, Leonardtown, MD 10 Sep 2025
ART

First Saturday of the Month Market Series

 22675 Washington St, The Bell Bldg Unit 106, Leonardtown MD 1 Nov 2025

Family Fest on the Potomac

 Piney Point Lighthouse Museum 13 Sep 2025
FESTIVALS

One Million Oysters for Breton Bay

 Abells Wharf Rd, Leonardtown, MD 20650, United States 13 Sep 2025

2025 Audience Participation Drum Circle Events

 St. Mary's County Arts Council 3 Oct 2025
ART

What the Heck is Happening?!

 The Inn at Leonardtown, Ascend Hotel Collection 27 Sep 2025
USD 30

Mystic Dead Quartet at the Planetarium

 STARS To STEM, Inc. 24 Oct 2025

First Saturday of the Month Market Series

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

2025 First Friday Drumline Events!

 22660 Washington St., Leonardtown, MD, United States, Maryland 20650 3 Oct 2025
FIRST-FRIDAY

A Top Gun Party Night!

 The Rex 27 Sep 2025
PARTIES

Redneck Rave at The Rex

 The Rex 26 Sep 2025
RAVES

The Great American Songbook

 Port of Leonardtown Winery 28 Sep 2025
MUSIC

More things to do in Leonardtown

Car Shows
Food & Drinks
Halloween
Live Music
Festivals
Parades
Pop-Ups
Carnivals
Food Truck Festivals