Upcoming Events in Leonardtown

Vendors of Southern MD

 Town Market LLC 20 Sep 2025
WORKSHOPS

Blessing of the Fleet 2025

 Leonardtown Wharf 4 Oct 2025
FIREWORKS

Outdoor Movie Night in LTown Alley

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

Cars & Coffee Car Show

 22675 Washington Street, The Bell Bldg Unit 106, Leonardtown, MD 24 Aug 2025
CAR-SHOWS

Wine & Whiff

 21935 Society Hill Rd , Leonardtown, MD, United States, Maryland 20650 16 Aug 2025
SPORTS

SMAWL Vaccination Clinic

 St. Mary's County Fairgrounds 8 Sep 2025
HEALTH-WELLNESS

Small Business Saturday with The Grinch & Cindy Lou Who

 Town Market LLC 29 Nov 2025
SHOPPING

Throwback Party!

 41655 Fenwick St, Leonardtown, MD 23 Aug 2025
PARTIES

8 Ball Scotch Doubles Pool Tournament

 Action Lounge and Billiards 16 Aug 2025
SPORTS

Free Concert on the Lawn featuring Unfinished Business

 21935 Society Hill Rd , Leonardtown, MD, United States, Maryland 20650 22 Aug 2025
CONCERTS

Friday Summer Skate

 Leonard Hall Rec Center 15 Aug 2025
CALENDAR

First Saturday of the Month Market Series

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

First Saturday of the Month Market Series

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

Faire Witch Project at The Rex Theatre

 22695 Washington St, Leonardtown, MD 2 Oct 2025
ART

August 29th Glass Blowing w/McFadden Art Glass

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

TSC Acoustic Live at the Planetarium!

STARS To STEM, Inc. 3 Oct 2025
ENTERTAINMENT

Team Trivia

 21935 Society Hill Rd , Leonardtown, MD, United States, Maryland 20650 14 Aug 2025

Hello Brunchy

 Botanic Cafe-Delicatessen 23 Aug 2025
BRUNCH

2025 First Friday Drumline Events!

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

Mystic Dead Quartet at the Planetarium

 STARS To STEM, Inc. 24 Oct 2025

More things to do in Leonardtown

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