First settled in 1684, Cambridge is one of the oldest cities in the country. Situated on the Choptank River, it has historically been a farming town. The city center has historic buildings fashioned in Federal Style; it may not be quite as picture-perfect as Easton, but the populace is less transplant-heavy and more authentically of the Shore (and it's diverse to boot – almost 50-50 split between white and African American). In Dorchester County, Cambridge is also the closest city to the new visitor center at the Harriet Tubman National Historical Park and its neighbor the Blackwater National Wildlife Refuge.

With level roads unfurling through a striking coastal landscape filled with farms, marshes and waterways, the county is an inviting cycling destination, and hosts two Ironman triathlons annually. Bird-watching and paddling are popular too.