Chesapeake Bay towns are old. But they’re cool-old. Many are older than the United States, established in the 1600s when colonists from Europe first came to North America.
Amazingly, Annapolis and Chestertown still have original colonial buildings. Residents of Smith and Tangier islands still speak in the style of their European ancestors who arrived hundreds of years ago.
St. Mary’s City and Poplar Island have been painstakingly recreated. While Cambridge, Chesapeake Beach and St. Michaels are hybrids, combining several generations of changes. Chesapeake City is a tiny town with tiny historic buildings.
The War of 1812 blew through the Chesapeake Bay. The Underground Railroad started rolling north from the Bay region while the Civil War was pushed south.
A lot of these quant villages are the hub of some of the best outdoor recreation — cycling, hunting, boating — that you’ll find in the country. These are small towns that are often found on national Top Ten lists.
The Chesapeake Bay covers more than 64,000 square miles, making it the biggest inland estuary in the United States. More than 150 rivers and streams flow in the 200-mile long Bay.
And that has lead to one of our Chesapeake Bay counties being home to more millionaires per capita than any other in the country. Some of these small, tucked-away towns have internationally-trained chefs and high-end shops, with nationally acclaimed artists and artisans stopping by.
You’ll see the Town-and-Country strolling through festivals along-side folk in camo-gear. The Chesapeake Bay draws all sorts of people for the same reasons: history and the out-of-doors fun and beauty.