Best Places to Retire by the Bay

Looking to settle down on the Bay? Here are a dozen places to check out.

Photos: Mark Sandlin/Talbot County Tourism

Easton, MD 

Population 16,500

The Talbot County seat hits many sweet spots for retirees. Its historic and attractive downtown evokes Mayberry and includes the Avalon Theatre, one of the Shore’s largest live performance venues., which ranks communities by how easily errands can be done on foot instead of in a driver’s seat, rates Easton “highly walkable.” The town is not on the Bay itself though there is a small marina on the Tred Avon River, and plans are in the works for more development there. But the Bay and its larger tributaries are close by, as is the charming waterside town tourist town of St. Michaels. Publishers ranging from Readers Digest to Kiplinger have praised Easton, the latter calling it “a great place to retire.”

Niche rating: A for Retirees

Waterside alternative—Chestertown, Md. (pop. 5,100) on the namesake Chester River mixes colonial quaintness with the youthful buzz of Washington College.