Entertainment events in Leonardtown

Check out happening entertainment events all around Leonardtown, MD

Vendors of Southern MD

 Sat, 20 Sep at 10:00 am Town Market LLC

Outdoor Movie Night in LTown Alley

 Fri, 26 Sep at 07:30 pm LTown Alley (Alice in LTown Mural) - 41676 Park Ave, Leonardtown, MD 20650, United States

Blessing of the Fleet 2025

 Sat, 04 Oct at 12:00 pm Leonardtown Wharf

Cars & Coffee Car Show

 Sun, 24 Aug at 10:00 am 22675 Washington Street, The Bell Bldg Unit 106, Leonardtown, MD

Small Business Saturday with The Grinch & Cindy Lou Who

 Sat, 29 Nov at 09:00 am Town Market LLC

Throwback Party!

 Sat, 23 Aug at 08:00 pm 41655 Fenwick St, Leonardtown, MD

Free Concert on the Lawn featuring Unfinished Business

 Fri, 22 Aug at 06:00 pm 21935 Society Hill Rd , Leonardtown, MD, United States, Maryland 20650

August 29th Glass Blowing w/McFadden Art Glass

 Fri, 29 Aug at 11:30 am 23190 Newtowne Neck Rd, Leonardtown, MD, United States, Maryland 20650

TSC Acoustic Live at the Planetarium!

Fri, 03 Oct at 07:00 pm STARS To STEM, Inc.

Death at the Disco

 Sun, 19 Oct at 06:00 pm Antoinette’s Garden USD 20

Live at Port of Leonardtown Winery

 Sat, 23 Aug at 02:00 pm Port of Leonardtown Winery

Hot Ice Live @ Port Of Leonardtown Winery

 Sat, 06 Sep at 02:00 pm Port of Leonardtown Winery

Levi Stephens LIVE

 Sat, 18 Oct at 05:00 pm 22845 Washington Street. Unit C, Leonardtown, MD

September Glass Blowing w/ McFadden glass

 Fri, 05 Sep at 12:30 pm 23190 Newtowne Neck Rd, Leonardtown, MD, United States, Maryland 20650

Puppet Show in the Park

 Sat, 20 Sep at 11:00 am Port of Leonardtown Park & Kayak Launch

2025 Audience Participation Drum Circle Events

 Fri, 05 Sep at 05:00 pm St. Mary's County Arts Council

For the first time ever!!!

Thu, 18 Sep at 07:00 pm The Rex

LHS Class of 2015 Reunion

 Sat, 13 Sep at 06:00 pm Port of Leonardtown Winery

Monster Mash Bash

 Sun, 19 Oct at 01:00 pm Leonardtown Wharf

Midnight Sunsets at The Rex

Thu, 21 Aug at 07:00 pm The Rex Theatre

Death at the Speakeasy

 Tue, 26 Aug at 06:00 pm Antoinette’s Garden USD 15

The Local Lemon at SPICE

 Fri, 29 Aug at 09:30 am 22725 Washington Street, Leonardtown, MD, United States, Maryland 20650

Chesapeake Mermaid at U.S. Oyster Festival

 Sat, 18 Oct at 12:00 pm St. Mary's County Fairgrounds

The Fenwick Inn presents a Mad Hatter's Tea

 Sun, 28 Sep at 12:30 pm The Fenwick Inn USD 50 to 71

US Oyster Festival

 Sat, 18 Oct at 10:00 am St. Mary's County Fairgrounds USD 5 to 24

Trunk or Treat & Vendor Show

 Sat, 25 Oct at 09:00 am Town Market LLC

Cars & Coffee Car Show

 Sun, 05 Oct at 10:00 am 22675 Washington Street, The Bell Bldg Unit 106, Leonardtown, MD

(Friday event} Salsa On The Vine at The Port of Leonardtown Winery.

 Fri, 19 Sep at 06:00 pm Port of Leonardtown Winery

Cars & Coffee Car Show

 Sun, 21 Sep at 10:00 am 22675 Washington Street, The Bell Bldg Unit 106, Leonardtown, MD

Come Out and See the Grinch & Christmas Shopping Spree

 Sat, 13 Dec at 09:00 am Town Market LLC

Awesome Scavenger Hunt! - Leonardtown Loot & Legends Hunt

 Wed, 04 Dec at 08:00 am 41680 Tudor Pl USD 15

Sunset Cruise @ Leonardtown Wharf

 Fri, 30 May at 06:15 pm Leonardtown Wharf