Maryland Baseball Leagues

The Charles-St. Mary's Baseball League is playing its eightieth season in 2026, which puts its founding around 1946 and makes it the second oldest league in this entire directory, behind only West Haven's 1933.

Eighty years in southern Maryland, at Rainbow Field in La Plata and across Charles and St. Mary's counties. This is tobacco country turned Washington exurb, and a league that started the year after the war ended has watched the whole transformation from the same set of diamonds. The site marks the anniversary with a tribute to Hal Willard, known as Hawk, and an alumni game, which is the correct way to handle eighty years: get the old players back on the field rather than into a banquet hall.

The operational details, divisions and fees and rosters, live on external pages we could not reach. The eightieth season is the story here anyway.

Chesapeake MSBL has been running since 1989 and carries thirty-three teams out of Annapolis. Its site answers browsers and returns a 403 to us, so the divisions and fee are published where we cannot quote them.

Thirty-three teams around Annapolis is a lot of baseball for a small city, and the explanation is the same one that explains the DC and northern Virginia leagues: this is a dense, wealthy, heavily populated corridor where a great many people work office jobs and grew up playing. The Chesapeake area supports four separate listings in our records, and a thirty-three team league is the anchor of them.

Thirty-seven years without interruption. Go to the site for the specifics.

The Dundalk-Eastfield Eastern Baltimore County Over 40 Baseball League has the longest name and one of the narrowest remits in this directory: over forty, east Baltimore County, and that is the whole specification.

Dundalk is a steel and shipyard town, Bethlehem Steel's Sparrows Point works having employed tens of thousands there before it closed. A league rooted in that specific place, restricted to men over forty, is playing with a roster of people whose fathers very likely worked the same ground.

The site says registration for the current season is closed and points at a Facebook group for anything up to date, which is a fair division of labour: the website exists to be found, the group exists to be useful. Contact runs through a form on the site.

The Ponce de Leon Baseball League has run since 1990 across the Washington metro, using high school and city fields through Montgomery County and northern Virginia. Four divisions: 30+, 48+, 60+, and a separate weeknight division for whoever cannot give up a weekend.

The name is a joke that has aged into a thesis. Ponce de León went looking for the fountain of youth and did not find it; a league that adopts his name for men over thirty is being wry about exactly what it is selling, and then, in January, runs a winter camp in Fort Myers, Florida. Which is to say the search continues, in the correct state, at the correct time of year.

Spring, summer and fall seasons, with 2026 fall registration having opened in June and closed August 14. They are currently short of umpires, which every league in this directory is and only some admit. [email protected], (703) 835-6701.