On the Water

Sunset Cruises

Immerse yourself in the natural beauty of St. Mary's waterways with two unique cruising experiences from Fish the Bay Charters.

Local Cuisine

U.S. Oyster Festival 2023

Enjoy fresh, local oysters, oyster shucking contests, an oyster cook-off, live entertainment, and more.

Island Excursion

Smith Island Cruises

Embark on a scenic day trip to Smith Island, Maryland's only inhabited offshore island.

Sep 23 - Sep 24

St. Mary's County Fair @ St. Mary's County Fairgrounds

Enjoy four days of fun at the St. Mary's County Fair! This classic fair is filled with rides, games, food, vendors, music, and so much more. Meet all sorts of...

Sep 26

Open House & Lecture @ U.S. Colored Troops Interpretive Center

Learn about the profound and significant contributions of St. Mary’s County’s U.S. Colored Troops (USCT) and Medal of Honor recipients at this two-part event....

Sep 29 - Oct 1

DME Racing Fall Nationals @ Maryland International Raceway

The Xxtreme Dragbike Association ends their season with the 31st annual DME Racing Fall Nationals at the Maryland International Raceway. The event features the...

Sep 29 - Sep 30

Sunset Cruises @ Point Lookout Marina

Admire the stunning scenery of the St. Mary's River with Captain Phil aboard the Lisa S., a 48-foot vintage Chesapeake Bay charter boat. This small-group...

Sep 30

Blessing of the Fleet @ Historic St. Mary's City

Historic St. Mary’s City is proud to be the backdrop for the 7th District Optimist Club 2023 Blessing of the Fleet, which celebrates St. Mary’s County’s ties...

Sep 30

Taste of St. Mary's @ Leonardtown Square

Spend your afternoon in the heart of Downtown Leonardtown sampling the best dishes that our local restaurants have to offer. This family fun event will have a...