An 'All-American' Scenic Byway On Maryland's Shores Goes Through Cute Towns And Historic Sites

The extraordinary Chesapeake Bay is America's largest estuary, encompassing nearly 12,000 miles of shoreline and spanning six states. Maryland's Eastern Shore, which wends along the Chesapeake Bay, boasts some of the region's most beautiful towns, historic sites, and scenic drives, all of which beg to be explored.

The Chesapeake Country Scenic Byway traverses over 430 land and nautical miles between Chesapeake City and Crisfield and is such a historically significant and stunning thoroughfare that it was named an All-American Road by the U.S. Department of Transportation's Federal Highway Administration in 2021. It's easy to fill a weekend driving along the winding route, which brims with sights to explore, including museums, manor houses, wildlife refuges, vineyards, beaches, lighthouses, and more. For fuel, savor some of Maryland's most famous delicacies, from freshly caught steamed blue crabs to the multi-layer Smith Island cake (the official dessert of Maryland).

If you want to start your route in Chesapeake City, it's about an 80-minute drive from Baltimore, one of the most underrated foodie destinations in America. Washington, D.C. is about an hour's drive from Stevensville, Maryland, on Kent Island, which is almost at the mid-point of the Byway. While the trip is beautiful year-round, the prime time to visit is during the summer months, when average temperatures hover around 75 degrees — perfect for water activities on the Bay. The fall is also beautiful as the leaves change on the Eastern Shore, and outdoor activities still abound with cooler weather.

The Chesapeake Country Scenic Byway will delight history buffs, nature lovers, foodies, and oenophiles with its diversity of experiences. If you're starting in Chesapeake City, stop by the historic C&D Canal Museum, where you can learn the story of the 19th-century canal connecting the Chesapeake and Delaware bays that happens to be one of the busiest in the country. Another historic site is the 17th-century Mount Harmon Plantation, a former tobacco plantation anchored by a restored Georgian-style manor house, which can be toured, and a boxwood garden designed by Thomas Jefferson.

Although Maryland may seem like an unlikely wine destination, Crow Farm Vineyard and Winery in nearby Kennedyville offers wine tastings of its "New World" varietals and even offers a bed & breakfast if you choose to stay overnight. For those looking for another luxurious stop to lodge, head further south to the charming town of St. Michael's and visit the elegant Inn at Perry Cabin, one of the most romantic honeymoon resorts in the U.S. Another unique place of interest is the Black Walnut Point Inn on nearby Tilghman Island, where you can sleep peacefully in the middle of a bird sanctuary.

The byway ends in Crisfield, an area known for its fresh seafood, nature reserves, and for being the gateway to secluded Smith Island, which is only reachable by ferry. Here, explore Janes Island State Park, a Chesapeake Bay salt marsh that offers hiking trails, beaches, and overnight camping. For an even more remote adventure, ferry over to Smith Island, where you can bike, kayak, and sample freshly caught crabs and delicious Smith Island cake.