This is the birthplace of Civil War activist Harriet Tubman. It has two modern waterfront parks while the town has maintained its cool, 1950/60's retro-downtown that's being revitalized with hip restaurants, a brewery, boutiques and antique shops
Popular on Top Ten travels lists, Chesapeake City is on the canal between Chesapeake Bay and Delaware Bay. Much of the historic village has been restored to it's turn-of-the century look. Huge cargo ships along with luxury yachts continually motor by the downtown making a very impressive view.
Chesapeake Bay towns don't get much more quaint than Chestertown. This county-seat has colonial mansions on the river, a town square with a huge Victorian fountain, a colony of semi-retired artists and festivals throughout the Spring, Summer and Fall.
Historic Easton is a unique mix of uber-wealthy waterfront mansion owners, and earthy watermen. Both are often hunters throughout the region. There are fashion boutiques near the downtown gun shop. They have gourmet restaurants and down-home cooking cafes. It's not on the water, but it's the center of water-life on the Eastern shore.
Havre de Grace is a popular getaway village for boaters & Baltimore residents. It has antique shops, boutiques and fun bars/restaurants. The downtown area is up a bit from the Chesapeake Bay entrance but still a great vista from certain places.
Downtown Rock Hall is all of two blocks long with a quaint, old-timey ice cream shop, a well-used regional music hall and a few stores. But get there on a festival weekend and the tiny town is rockin'. Aside from festivals, it's best known for two big crab-house/dock-bars and a couple small, gourmet restaurants.
Solomons, also called Solomons Island, is an town of about 2,300 where the Patuxent River flows in the Chesapeake Bay. During the summer, the population can go as high as 15,000 as boaters fill the huge marinas. There is no beach, but there are big waterfront bars that are hugely popular.
St. Mary's City is the most intact 17th century English town in the U.S. It's been recreated as it was, using the foundations located under a farm field. St. Mary's City was also Maryland's first capitol, when the state was a colony.
St. Michaels is a great weekend escape location. It has numerous restaurants, boutiques, spas, antique stores and a huge maritime museum. There's also a winery, brewery and distillery. Plenty of interesting day-tripping places nearby. The highways have wide shoulders for excellent cycling. And the town has a lively nightlife.
Tangier Island is a lot like Smith Island, but it's on the Virginia end of the Chesapeake Bay. This is where you go to get a real Chesapeake Bay crab cakes. It also has an amazing, pristine white-sand beach. You can get there only by boat.