Veterans Day Parade and Memorial Wreath Laying Ceremony

Town of Leonardtown 11 Nov 2026

Christmas on the Square & Annual Tree Lighting

Town of Leonardtown 27 Nov 2026

SMAWL Low Cost Vaccination Clinic

St. Mary's County Fairgrounds 9 Nov 2026

Gangsters & Gals dance party

The Rex Theatre 14 Nov 2026

Home for The Holidays - A New St. Mary's County Holiday Tradition

Saint Mary's Fairgrounds 5 Dec 2026

Harry Potter Mystic Market & First Saturday of the Month

22675 Washington St, The Bell Bldg Unit 106, Leonardtown MD 7 Nov 2026

FOLs Fall BOOK Sale - Bigger & Better!

42455 Fairgrounds Rd, Leonardtown, MD 20650, United States 7 Nov 2026

GTA Pre-Release Theme Party!

22695 Washington St, Leonardtown, MD 13 Nov 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

Open Water Diver – Scuba Certification Weekend Class

College of Southern MD-Leonardtown 13 Jun 2026

LVRSA Night at LEDO Pizza, Leonardtown

Ledo Pizza (Leonardtown, MD) 4 Nov 2026

Discover Scuba Diving – Try Scuba Experience

College of Southern MD-Leonardtown 12 Sep 2026

Watercolor Blooms Painting Party

22694 Washington St 10 Nov 2026

Re-Activate – Scuba Refresher Program Weekend Course

College of Southern MD-Leonardtown 15 Nov 2026

Author Fair

Leonardtown Library and Garvey Senior Activity Center 7 Nov 2026

Pictures with Santa Clause

Town Market LLC 19 Dec 2026

Vampire Masquerade Ball

The Rex 13 Feb 2027

FREE Individual Cessation Classes available through The St. Mary's County Health Department

21580 Peabody St, Leonardtown, MD, United States, Maryland 20650 30 Sep 2026

Knight and the Moth Bookclub Meet up

Kneaded Baking Co 8 Nov 2026

Photos with Santa! (Pet **all species** and kid friendly)w

Balanced Paws Pet Care 13 Dec 2026