Once considered just a gritty seaport, Cambridge has a blossoming downtown, water accessibility, and affordable prices that have made it a hot destination—and a popular place to retire. Visitors can bike, drive, or walk the scenic Blackwater National Wildlife Refuge or get out on the refuge’s waterways with Blackwater Paddle and Pedal and look for bald eagles and sika deer.
Enjoy Sunday-night tapas with the locals at Bistro Poplar (535 Poplar St.; 410-228-4884), a local brew at Realerevival Brewing (504 Poplar St.; 443- 225-5664), or pizza and risotto cakes at Stoked Wood Fired Eatery (413 Muir St.; 443-477-6040). Stay at the Hyatt Regency Chesapeake Bay (100 Heron Blvd. at Route 50; 410-901-1234) and relish a great view of the Choptank River. Add a round of golf and a hot-rock massage and call it a day.
Distance from DC: 88 miles.
Nearby: The Harriet Tubman Underground Railroad Byway, a self-guided driving route past 30 historic sites.