When the British colonized America and gradually built out towns, High Street became a key landmark. The roadway typically led directly from the waterfront to the highest point of land (to avoid flooding) where the British officials often constructed a courthouse, church, and jail. The inside joke: townspeople could be judged, punished and redeemed on the same street corner.
You breeze into Cambridge, Maryland via the 50-foot high Malkus Bridge that spans the upper Choptank River. Alongside runs a footbridge, populated with eager fishermen casting for their daily catch of rockfish. Home to seven governors, sharpshooter Annie Oakley, the Underground Railroad’s Harriet Tubman and a pack of other notorious characters, Cambridge has a long and storied history.
Founded in 1864, Cambridge was once a harbor for trading ships taking tobacco to England and later served as a deepwater port for 20th-century freighters. It was also a shipbuilding town. The town still draws plenty of pleasure boaters. At the Long Wharf visitors will find an impressive waterfront park with expansive lawns and the Cambridge Yacht Basin. The neighboring Cambridge Yacht Club hosts several sailing regattas throughout the year that draws large crowds.
Oystering still plays a large role in the local economy. The Choptank Oyster Company brand of Choptank Sweets is a robust, meaty oyster with a sweet, buttery flavor and a clean, crisp finish. The moderate salinity of the river allows for the complex natural flavors of this tasty oyster.
The skipjack is the last fleet of working sailing vessels in North America. Maryland’s official state boat, the skipjack is named after the species of fish noted for their speed. The vessels date from the 1890s and are noted for shallow drafts and maneuverability. There are no winches, just manpower, and blocks and tackle. The skipjack’s beamy, open deck— necessary for wintertime oyster dredging under sail— creates a very stable ride. Not many of these graceful boats are left, so consider a cruise on the 65-foot Nathan of Dorchester to get a feel for the hard work that goes into earning a living from the bay. One and three-hour narrated heritage tours leave from Long Wharf on a regular schedule.
A pair of downtown museums salutes the region’s maritime heritage. The Richardson Maritime Museum & Boatworks honors wooden boats with display models of skipjacks, log canoes and other boats that traditionally plied the waters of the Chesapeake. The smaller Brannock Maritime Museum houses a collection of maritime artifacts and photos.
Take a stroll along the wide brick paved, tree-lined High Street and marvel at some of the most impressive architecture on the Eastern Shore. The graceful 18th and 19th-century homes were once residences of politicians, attorneys, merchants and sea captains. Adorned with elaborate turrets, stained glass panels, expansive wrap-around porches, copper roofs and columned entrances, the homes represents different periods and styles, including Federal and Queen Anne.
Keep going up High Street until you come to Poplar Street. It’s Cambridge’s Arts and Entertainment District with shops, galleries and an array of restaurants. Stop in at the Center for the Arts. It’s home for artists in assorted media— drawing, painting, including watercolor, pastels, and oils. You will also find basketry, pottery, quilting, photography, stained glass, music, theater, and literature.
A legendary sharpshooter for Buffalo Bill’s Wild West spectacle, in 1912 Annie Oakley and her husband constructed their Colonial Revival bungalow at 28 Bellevue Avenue on Hambrooks Bay. The house retains many of its original features including floor to ceiling trophy cases in the living room and a kitchen crafted for a five-foot tall woman. The roof line was altered so Oakley could step outside her second-story windows and shoot waterfowl coming in over the bay. The house is now privately owned, but the owners have a plaque in Annie’s memory.
J.M. Clayton Company claims to be the oldest (1890) working crab house in the world. For five generations the Chesapeake Bay blue crabs have been delivered fresh daily to its doors by local watermen. Crowds flock here throughout the summer months for steamed and seasoned crabs, served on brown paper. They are armed with the tools of this trade, a wooden mallet in one hand, a paring knife in the other as they dive into jumbo crabs.
Another favorite spot is Jimmie & Sook’s Raw Bar and Grill. The interior is outfitted with the working tools and relics used by generations of local watermen, as well as local photos that serve as a visual history of the people, place, and culture of Maryland’s Eastern Shore. Their signature award-winning dish is the crab dip served in a warm bread bowl. While the seafood is absolutely heavenly, the brisket, ribs, and chicken dishes also earn high marks. Top off the meal with molten lava cake and a scoop of ice cream. So where did the name originate? From the common term used for a male blue crab, a Jimmie, and a mature female crab, a Sook.
Stoked Wood Fired Eatery is celebrated for its artisanal pizza baked in a wood-fired stove. Owner and chef Patrick Fanning has created a cozy setting with chalkboards on the walls spotlighting menu items. Guests can begin with an appetizer of shrimp and grits or mozzarella sticks. Sandwich selections include lobster rolls, charcuterie panini, veggie panini, chicken parmesan and Italian-dip-panini. Favorite entrées are pasta primavera, jumbo shrimp and crab cake.
If you’re looking for an extended trip beyond Cambridge, twelve miles south is the Blackwater Wildlife Refuge. Referred to as the “Everglades of the North,” the 27,000-acre wildlife refuge is comprised of rich tidal marshes and forests home to some of the most important habitat for birds along the critical migration highway called the Atlantic Flyway. Get an up-close view of ospreys in flight or proud blue herons stalking the marsh grasses. The refuge is best known for birds of prey, such as hawks, the migrant peregrine falcon and the largest breeding population of American bald eagles on the East Coast north of Florida.