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

Blessing of the Fleet 2026

Leonardtown Wharf 3 Oct 2026

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

Saint Mary's Fairgrounds 5 Dec 2026

Monster Mash Bash

Leonardtown Wharf 24 Oct 2026

Arts & Entertainment Celebration First Friday

Leonardtown Square 4 Sep 2026

The Joe Cox Band LIVE @ The Rex Theatre

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

Outdoor Art & Movie Night

Town Market LLC 19 Sep 2026

Faire Witch: Ladies Night Out

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

Infinity Day Celebration

Port of Leonardtown Park & Kayak Launch 8 Aug 2026

Jackson Perkins Live at the Rex Theatre

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

90's Country Night by Hat Trick Band @ The Rex Theatre!

22695 Washington St, Leonardtown, MD, United States, Maryland 20650 13 Aug 2026

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

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

Game Day with St. Mary's Democrats

Action Lounge and Billiards - 25470 Point Lookout Road Leonardtown, MD 20650 8 Aug 2026

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

The Inn at Leonardtown, Ascend Hotel Collection 8 Sep 2026

Trunk or Treat & Vendor Show

Town Market LLC 24 Oct 2026

TRX Pilates Strength & Stretch

41566 Medleys Neck Road, Leonardtown, MD, United States, Maryland 20650 7 Aug 2026

Friday Summer Skate

Leonard Hall Rec Center 17 Jul 2026

Back To School Pop Up Shop

Leonardtown, Maryland 8 Aug 2026