St. Mary's County Fair - 2026

St Marys County Fair 24 Sep 2026

2026 Leonardtown Art Walk - First Friday Launch

22660 Washington St., Leonardtown, MD, United States, Maryland 20650 4 Sep 2026

Arts & Entertainment Celebration First Friday

Leonardtown Square 4 Sep 2026

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

The Inn at Leonardtown, Ascend Hotel Collection 8 Sep 2026

Seafood Feast

Fitzie's Marina & Pub 12 Sep 2026

Outdoor Art & Movie Night

Town Market LLC 19 Sep 2026

Blessing of the Fleet 2026

Leonardtown Wharf 3 Oct 2026

2026 First Friday Audience Participation Drum Circle

22660 Washington St., Leonardtown, MD, United States, Maryland 20650 5 Jun 2026

EllaChella Day Party!

22695 Washington St, Leonardtown, MD 19 Sep 2026

Vendors of Southern MD

Town Market LLC 12 Sep 2026

One Million Oysters for Breton Bay

Abells Wharf Rd, Leonardtown, MD 20650, United States 12 Sep 2026

Weekly Sound Reset

22660 Washington St 6 Jul 2026

TRX Pilates Strength & Stretch

41566 Medleys Neck Road, Leonardtown, MD, United States, Maryland 20650 4 Sep 2026

Arts & Entertainment Celebration First Friday

22699 MD-326, Leonardtown, MD 20650-3848, United States 5 Sep 2026

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

St. Mary's County Fairgrounds 12 Oct 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

Senator Jack Bailey’s 5th Annual Bull Roast

Olde Breton Inn and Bailey's Catering 10 Sep 2026

End of Summer Bash

Leonardtown Wharf 5 Sep 2026

Open Water Diver – Scuba Certification Weekend Class

College of Southern MD-Leonardtown 13 Jun 2026

Senator Jack Bailey’s Golf Tournament

Breton Bay Golf & Country Club 10 Sep 2026