Take your time experiencing the special beauty of this tidewater region with its pristine waterways and vibrant historic waterfront villages.
Open for Exploration
Equal parts celebration and foodie feast, there's nothing quite so quintessentially Chesapeake as good, old-fashioned Maryland steamed crabs.
Mid-Shore section from Wye Mills to Vienna
Including US 50, MD 322, MD 33, MD 333, MD 341 & MD 192
Head East on US 50 to Wye Mills and tour the Old Wye Grist Mill, to witness the oldest continuously working water-powered grist mill in the country. During the American Revolution, the Wye Grist Mill shipped barrels of flour via the Chesapeake Bay to the Continental Army, commanded by General George Washington. Historians dubbed the Eastern Shore the “Breadbasket of the Revolution."
A sidetrack to the charming town of Denton leads to the Choptank River waterfront and the Museum of Rural Life. Exhibits of four historic dwellings inside the museum provide a rare glimpse into the lifestyles of residents who, for 300 years, solely depended upon agriculture to earn a living.
Back on the main route, travel to Easton and beyond to the Tilghman Island peninsula.This area, with its bayside beauty and more than 350 years of history, inspired James Michener to write the epic novel Chesapeake. In Easton, the restored, art deco Avalon Theatre hosts nationally known performing artists, while crafters display their wares at nearby specialty shops. You can also tour a winery, get a taste of the dining scene or enjoy outdoor activities ranging from hiking and canoeing to championship golf.
St. Michaels, a former shipbuilding center now popular among pleasure boaters, features the Chesapeake Bay Maritime Museum with its working boatyard and restored 1879 lighthouse. Just down the road is Tilghman Island, which offers skipjack cruises and fine local cuisine. Head to Bellevue, where a historic ferry crosses the Tred Avon River to reach Oxford, another boating town with its own museum. Bike routes throughout the flat land, such as the Oxford - St Michaels Bike Trail, have wide-open country views. Also in the area are the captivating colonial town of East New Market and the tiny fishing village of Secretary.
Cross the wide Choptank River and enter the city of Cambridge. On the waterfront at Long Wharf, the Choptank River Lighthouse creates an idyllic scene that belies the busy port that once existed here. Experience the scenic view aboard the Skipjack Nathan. In its historic downtown, Cambridge’s active arts scene and a large maritime museum add to the cultural fabric of the city. Learn about Harriet Tubman's daring rescue missions at the Harriet Tubman Underground Railroad National Scenic Byway. Natural splendor is found at sites such as the Blackwater National Wildlife Refuge, which hosts the East Coast’s largest nesting population of bald eagles.
Bike the 6 miles across Kent Island on the Cross Island Trail and take in sweeping views of the Bay.
For an unmatched view of Georgetown Harbor, dine on the deck at the Kitty Knight House. Miss Kitty Knight is credited with saving part of Georgetown from burning by British soldiers during the War of 1812.
Farm stands and agritourism attractions are a staple of the drive along the Chesapeake Country Byway. Crow Farm and Vineyard, between Kennedyville and Galena, includes a farmstay B&B, local wines and grass-fed beef.
Explore wild, scenic areas along the byway, including the Blackwater National Wildlife Refuge, Hooper Island and Elliott Island, after a stop within the Fishing Bay Wildlife Management Area, nicknamed “Maryland’s Everglades."
Celebrated author James Michener wrote an outline for his novel Chesapeake in an Oxford tavern that won his heart with its succulent crab cakes.