St. Mary’s Freedom Fest

St. Mary’s Freedom Fest 3 Jul 2026

29th Run & Fun Walk for Hospice of St. Mary’s

St. Mary's County Recreation & Parks 11 Apr 2026

Luck of the Draw

25470 Point Lookout Rd Leonardtown, MD 20650 24 Jan 2026

Foreign Company-The Rex Theater Leonardtown MD

The Rex 31 Jan 2026

Anti-Valentines Day Event

41655 Fenwick St, Leonardtown, MD 13 Feb 2026

SDVFDRS Auxiliary Spring Craft Vendor Fair & Community Yard Sale

St. Mary's County Fairgrounds 7 Mar 2026

Spring Fling Open Market & Car Show

22675 Washington Street, The Bell Bldg, Leonardtown MD 26 Apr 2026

2026 SOUPER Bowl!

22730 Washington St, Leonardtown, MD, United States, Maryland 20650 7 Feb 2026

Salsa on the Vine- Jan

23190 Newtowne Neck Rd, Leonardtown, MD, United States, Maryland 20650 24 Jan 2026

Galentine's Sip & Shop Happy Hour

22695 Washington St, Leonardtown, MD, United States, Maryland 20650 12 Feb 2026

Re-Activate – Scuba Refresher Program Weekend Course

College of Southern MD-Leonardtown 25 Jan 2026

Charcuterie Date Night w/ Hicks Creations

23190 Newtowne Neck Rd, Leonardtown, MD, United States, Maryland 20650 30 Jan 2026

First Saturday of the Month Market Series

22675 Washington St, The Bell Bldg Unit 106, Leonardtown MD 2 May 2026

Valentines Day Event at MJ Luxe Medi Spa

25450 Point Lookout Rd Suite 1, Leonardtown, MD 7 Feb 2026

Men's Breakfast

22730 Washington St, Leonardtown, MD, United States, Maryland 20650 31 Jan 2026

Silent book club-SOMD Feb 2026

Antoinette's Garden 13 Feb 2026

Hot Ice Live @ Action Lounge and Billiards

25470 Point Lookout Rd, Leonardtown, MD 20650-3828, United States 28 Feb 2026

Galentines COOKIE decorating class

23190 Newtowne Neck Rd, Leonardtown, MD, United States, Maryland 20650 13 Feb 2026

Historic Lecture: The Brick Chapel at St. Mary's City

41770 Baldridge Street, Leonardtown, MD, United States, Maryland 20650 29 Jan 2026

Discover Scuba Diving – Try Scuba Experience

College of Southern MD-Leonardtown 24 Jan 2026