St. Mary's County Fair - 2026

St Marys County Fair 24 Sep 2026

Summer Smash 2.0

The Rex 8 Aug 2026

Paws &Popcorn Movie Night: The Lion King

Meow Dyer Cat Cafe, LLC 14 Aug 2026

SMBC Boat Regatta the Wharf

Leonardtown Wharf 25 Jul 2026

Monster Mash Bash

Leonardtown Wharf 24 Oct 2026

Arts & Entertainment Celebration First Friday

Leonardtown Square 4 Sep 2026

Infinity Day Celebration

Port of Leonardtown Park & Kayak Launch 8 Aug 2026

Outdoor Art & Movie Night

Town Market LLC 19 Sep 2026

The Joe Cox Band LIVE @ The Rex Theatre

22695 Washington St, Leonardtown, MD, United States, Maryland 20650 29 Aug 2026

Christmas In July @ The Rex Theater 🎄

22695 Washington St, Leonardtown, MD, United States, Maryland 20650 25 Jul 2026

Friday Summer Skate

Leonard Hall Rec Center 17 Jul 2026

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

21580 Peabody St, Leonardtown, MD, United States, Maryland 20650 10 Aug 2026

2026 Sultana Adult Paddling Experience-St. Mary's, MD

The Inn at Leonardtown, Ascend Hotel Collection 8 Sep 2026

What If? A Sunday Brunch for Women Quietly Wanting More

Botanic Café 19 Jul 2026

NEG Anniversary Gala Dinner - October 8th 5-8pm

Botanic Café 8 Oct 2026

TRX Strength & Stretch with Andrea Wilson

41566 Medleys Neck Road, Leonardtown, MD, United States, Maryland 20650 17 Jul 2026

Christmas In July!

22695 Washington Street, Leonardtown, MD 17 Jul 2026

Harry Potter Mystic Market & First Saturday of the Month

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

Smoke-Fire-Fore! ALVFD Golf Tournament

Breton Bay Golf & Country Club 31 Jul 2026

Jackson Perkins Live at the Rex Theatre

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