The Chesapeake Country All American Road experience stretches from its upper Eastern Shore terminus, the picturesque Chesapeake and Delaware Canal, an engineering marvel and cultural boundary, to its lower shore recreational terminus at Smith Island, where on foot, by bike, or by boat, it is easy to absorb the essence of where "life flows gently with the tide". In between, it meanders along its spine of winding roads and collection of sidetracks that lead to pristine views of the Bay and its tributaries. The pleasures of the Byway unfold in towns such as Chestertown, Easton and Salisbury that reflect early colonial settlements and their role as the country's crucible of 19th century African-American leadership. The Byway's abundant beauty remains much as it was when the "Nanticoke peoples", descendant groups of the Nanticoke tribe, roamed over land and water prior to British colonization.
The National Park Service's Chesapeake Bay Special Resource Study describes the cultural context of the CCSB landscape as, "The Chesapeake Bay is nationally significant in part because it possesses exceptional value or quality in illustrating or interpreting the themes of our nation's natural and cultural heritage. The Bay provides an exceptional opportunity for interpreting the interdependence of cultural and natural resources, both in its modern condition and its nearly 300-year history". Exemplifying this significance are CCSB working waterfronts, such as Rock Hall, Kent Narrows, Cambridge, and Crisfield, where watermen, the unique term for those making their living from the Bay, hold a prominent place in the region's culture, economy, and mystique. Working year-round, watermen harvest rockfish, oysters, and crabs and many still use the Chesapeake dialect that evolved from the Eastern Shore's near-isolation prior to the 1950 construction of the Bay Bridge. Some of these watermen have become Certified Chesapeake Bay Storytellers© offering guided-tour excursions on authentic "deadrises" where visitors can work the Bay by boat, capture its bounty and have their meal served "dock to table". Iconic skipjacks, a tribute to the age of sail with their "long lifting bowsprit, raked wooden mast and sweeping sheer lines" and a collection of "screwpile" lighthouses designed specifically for the sandy bottom of the Chesapeake Bay are other unique nautical symbols accessed on the Byway. Throughout the year, events such as Downrigging Weekend, the Waterfowl Festival, and the Nanticoke Indian Pow Wow bring to life the distinctive cultural heritage of Chesapeake Country.
Chesapeake Country All American Road offers superlative opportunities for recreation. The Bay's open waters, tidal rivers, and shorelines, as well as dozens of parks and refuges and an extensive system of land and water trails, provide excellent opportunities for public use, enjoyment, education, and scientific study. From birdwatching on the Atlantic Flyway, sailing, fishing, hiking, and pedaling land-trails, paddling water-trails, the CCSB is an outdoor adventurer's dream.
The Captain John Smith Chesapeake National Historic Trail, the first historic national water trail, with access points all along the Byway, combined with the connecting Maryland system of water trails, provides world-class on-the-water recreational experiences second-to-none. Each trail is a window into the indigenous cultural landscape that existed before British colonization. It is where visitors feel "Chesepiooc", an Algonquian word meaning "great water". The trails are easily accessible from dozens of locations along the Byway and visitors may experience the trails independently or utilize local guides and outfitters. The exceptional recreational activities on the water trails are both passive and active. They include paddling, power-boating, cruising, jet-skiing, sailing, canoeing, floating, fishing, birdwatching, oystering, crabbing, and swimming. One of the most unique features of the water trail system is the "one-of-a-kind" smart buoys that are designed to deliver near real-time information on weather and water conditions, provide trail users with navigational information, and interpret that specific location on the Chesapeake Bay 400 years ago. Visitors can also follow the Captain John Smith Geotrail to explore nearly 50 places associated with the adventures of Captain Smith and his crew. Water trail maps are distributed at many of the trail access points and by the NPS and the Maryland Department of Natural Resources.
The byway route itself, with gently rolling hills, tidewater flatlands and wide, paved shoulders, draws cyclists from around the world. "This is a trip to relish! Imagine pedaling along the coast of the Chesapeake Bay, through the farmlands of the Eastern Shore, around historic towns, relaxing on the coast, and dining on fresh oysters and crab cakes, all while enjoying the ease of riding the flat coastal terrain".
The Byways scenic resources – its rural landscapes, historic townscapes, natural and working waterfronts with their unusual level of integrity and coherence are representative of the Eastern Shore's unique heritage and culture. The overall scenic experience can be described as traveling through wide-open landscape spaces, alternating with brief periods of enclosed corridor like forested spaces. Punctuating this overall experience are distinct or special scenic episodes, including historic towns and villages, broad view-sheds of the Chesapeake Bay, rivers, fishing wharves, and large farmsteads.
Chesapeake Country Scenic Byway's concentration of and abundant access to the Chesapeake Bay's recreational and scenic features, coupled with its culture and history, no doubt makes it a destination not to be missed.