Upcoming Events in Leonardtown

Strutter - KISS Tribute

 The Rex Theatre - MD 10 Oct 2025
ART

Small Business Saturday with The Grinch & Cindy Lou Who

 Town Market LLC 29 Nov 2025
SHOPPING

Harry Potter Mystic Market & First Saturday of the Month

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

First Saturday of the Month Market Series

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

Leprechaun Lilly's Kids Consignment Sale - 2025 Fall/Winter

 42455 Fairgrounds Rd, Leonardtown, MD, United States, Maryland 20650 9 Oct 2025
KIDS

Paint Your Pet's Portrait Fundraiser

Wine & Design (Leonardtown, MD) 14 Nov 2025
NONPROFIT

Hit or Miss Halloween!!

22695 Washington St, Leonardtown, MD 31 Oct 2025
HALLOWEEN

Pre-Pride Social Hour

 Port of Leonardtown Winery 10 Oct 2025

Social’s Slasher Night!

 41655 Fenwick St, Leonardtown, MD 25 Oct 2025
HALLOWEEN-PARTIES

Sabbath @ The Rex !

 The Rex 8 Nov 2025

U.S. Oyster Festival

 St. Mary's County Fairgrounds 19 Oct 2025
FESTIVALS

Oct 10th: Leonardtown, MD - MAGIC HUNKS Live at The Rex Theatre

 The Rex 10 Oct 2025
ART

PADI Open Water Scuba Diver Course

 Csm Leonardtown Campus 8 Nov 2025
WORKSHOPS

Chinoiserie Pumpkins at Dixon Family Farm Pumpkin Festival

 41610 Fenwick St, Leonardtown, MD 20650 25 Oct 2025
FESTIVALS

Monster Mash Bash

 Leonardtown Wharf 19 Oct 2025
HALLOWEEN

Bootleggers at POL Winery

 Port of Leonardtown Winery 11 Oct 2025

2025 Leonardtown Square Fall Bar Crawl

 Leonardtown Square 10 Oct 2025
PARTIES

Gingerbread Paint Party

 Brudergarten Beer Garden at Shepherd’s Old Field Market 12 Oct 2025
PARTIES

Bootleggers at Oysterfest

St. Mary's County Fairgrounds 18 Oct 2025
PERFORMANCES

Autumn Wreath making workshop

 23190 Newtowne Neck Rd, Leonardtown, MD, United States, Maryland 20650 15 Oct 2025
WORKSHOPS

More things to do in Leonardtown

Halloween
Food & Drinks
Festivals
Live Music
Christmas Markets & Fairs
Trunk Or Treat
Parades
Christmas Wreath Workshops
Christmas Carols
Food Truck Festivals