U.S. Oyster Festival

St. Mary's County Fairgrounds 17 Oct 2026

Veterans Day Parade and Memorial Wreath Laying Ceremony

Town of Leonardtown 11 Nov 2026

Rabies Clinic with SMAWL @ St. Mary's Fair Grounds

St. Mary's County Fairgrounds 12 Oct 2026

Coastal Arts Market

Leonardtown Wharf Park 10 Oct 2026

Jackson Perkins Live at the Rex Theatre

22695 Washington St, Leonardtown, MD, United States, Maryland 20650 17 Oct 2026

Monster Mash Bash

Leonardtown Wharf 24 Oct 2026

Faire Witch: Ladies Night Out

22695 Washington St, Leonardtown, MD, United States, Maryland 20650 8 Oct 2026

Christmas on the Square & Annual Tree Lighting

Town of Leonardtown 27 Nov 2026

Willett Exclusive Release Event

SOCIAL Coffeehouse & Cocktail Bar 20 Oct 2026

Trunk or Treat & Vendor Show

Town Market LLC 24 Oct 2026

SMAWL Low Cost Vaccination Clinic

St. Mary's County Fairgrounds 9 Nov 2026

Black Velvet: A Lounge Experience

41655 Fenwick St 30 Oct 2026

Cars & Coffee Car Show - Trunk or Treat

22675 Washington Street, The Bell Bldg Unit 106, Leonardtown, MD 24 Oct 2026

Bedazzle night

Antoinette’s Garden 20 Oct 2026

Open Water Diver – Scuba Certification Weekend Class

College of Southern MD-Leonardtown 13 Jun 2026

The Old Jail Museum Open for Leonardtown First Fridays (Extended Hours) (FREE)

41625 Courthouse Dr, Leonardtown, MD, United States, Maryland 20650 4 Sep 2026

FAW Crusader Cup 2026

Breton Bay Golf & Country Club 23 Oct 2026

Sins And Secrets After Dark

The Rex 30 Oct 2026

Howl-Owen PAWTY!

22725 Duke St, Leonardtown, MD 25 Oct 2026

WITCHES OF SOUTHERN MD 2026

Leonardtown Wharf 23 Oct 2026