6 minute read
Maryland’s Chesapeake Country
Chestertown, a Colonial port and National Historic Landmark, is home to Washington College.
Photo courtesy Kent County Tourism.
Hooper Lighthouse, Chesapeake Bay Maritime Museum, St. Michaels.
Maryland’s Chesapeake Country follows 419 miles from Chesapeake City to Crisfield on country roads along the bay’s edge and part of the Great Chesapeake Bay Loop. Maryland’s Eastern Shore is divided into three regions.
Upper Eastern Shore
Discover a patchwork landscape of eclectic small towns draped across the pristine beauty of Maryland’s gorgeous Eastern Shore. Experience the shore’s centuries-old tradition of hospitality served with a heaping side of unparalleled Maryland seafood (crabs, oysters, rockfish – no need to choose, try them all!) and the remarkable waters of the Chesapeake Bay. Take your time experiencing the special beauty of this tidewater region with its pristine waterways and vibrant historic waterfront villages. From Chesapeake City, you can look out over the 14mile-long Chesapeake and Delaware Canal to see modern-day ships dwarfing Victorian homes and shops along the banks.
The C&D Canal Museum captures the history of the 165-year-old waterway. A side trip reveals the graceful beauty of Mount Harmon Plantation in Earleville. This 200-acre colonial plantation, featuring an antiques-filled manor house museum and walking trails, is on a peninsula surrounded by the Sassafras River. Across the river is Georgetown, which the British burned during the War of 1812 but has been rebuilt and is a popular place for dining and entertainment. Continue toward Galena and on to Kennedyville, where you will find Crow Farm Vineyard and Winery. Stop at the Kent Museum to see displays of antique tractors, horse-drawn sleds and household equipment. Head to Chestertown, a colonial port and National Historic Landmark, which is home to Washington College, founded in 1782 and named for its patron, George Washington. Among the elegant brick town homes in the city’s Historic District you can enjoy concerts in the square.
Washington College was the first college chartered in the sovereign United States of America. General George Washington lent his name, donated 50 guineas to the founding and served on the first Board of the college. Chestertown is a historic town along the banks of the Chester River. The brick sidewalks lined with shops, restaurants and inns welcome visitors to meander and browse. A visit to Chestertown’s Historic District to admire the fine colonial residences is a must. Get out on the water on the Captain John Smith National Historic Water Trail with a paddling or sailing tour led by the Sultana Education Foundation. On board the Schooner Sultana, you can connect to the Chesapeake Bay’s history, ecology and culture, and become inspired to be a part of preserving and restoring America’s largest estuary. Sultana’s Downrigging Weekend Tall Ship and Wooden Boat Festival in late October has evolved into one of the largest annual Tall Ship gatherings on the East Coast. Serving as Kent County’s seat of government since 1706, Chestertown has been a Royal Point of Entry, the scene of its own Revolutionary Tea Party in 1774, and the hub of a bustling agricultural and seafood region.
Kent County Horse Farm
Photo courtesy Kent County Tourism
The Schooner Sultana, connecting Chesapeake Bay’s history, ecology and culture.
Photo courtesy Sultana Education Foundation.
With fall upon us, Kent County invites visitors to explore the crisp, cool, and refreshing season. A fall escape filled with leaf peeping hikes, or a tranquil paddling adventure are the perfect components for your next getaway. Whether driving or cycling its two-lane roadways, you will discover calming landscapes of low, rolling farmland, dramatic sunsets, and rich heritage. Home to some of the most quaint and delightful towns (Chestertown, Rock Hall, Galena, Betterton, and Millington), you will be enthralled by exploring the historic architecture, enjoying visual and performing arts, savoring wines from local vineyards, sampling concoctions at the resident distillery or shopping along red-brick sidewalks. Veer southwest to Rock Hall, which has more than a dozen marinas offering mooring and charter services.
The town also prides itself on excellent seafood dining, a homemade ice cream shop and a small, maritime-oriented museum. The Eastern Neck National Wildlife Refuge, an isolated ecosystem with nesting bald eagles and extensive hiking trails, is just to the south. The area that extends from Chestertown through Centreville and into Queenstown is famous for its large number of fine antiques shops. But you can also find bargains on name-brand items at Premium Outlets. Along the way, make a stop at the Museum of Eastern Shore Life to admire an eclectic collection of artifacts ranging from a log canoe to early hand tools.
Middle Eastern Shore
Hiking the trails in Kent County.
Avalon Theater, Easton.
Photo courtesy Willow Construction.
Kayaking the Captain John Smith National Historic Water Trail.
Photo courtesy Kent County Tourism
Head east on U.S. 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”. 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.
Easton has been the sophisticated center of the Eastern Shore since its founding in 1790. Today it’s known for its excellent restaurants, outstanding lodging, an assortment of upscale boutiques plus its studios and galleries abuzz in a vibrant arts scene. In Easton, the restored, art deco Avalon Theatre hosts nationally known performing artists, while crafters display their wares at nearby specialty shops. 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. 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. Learn about Harriet Tubman’s daring rescue missions at the Harriet Tubman Underground Railroad National Historical Park. 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.
Lower Eastern Shore
Harriet Tubman Underground Railroad National Historical Park in Dorchester County, Maryland.
Photo courtesy Acroterion and Wikimedia Commons CC BY-SA 4.0
From Vienna, known for its rich Nanticoke River and Chesapeake Bay legacy, this section of the byway has two travel options. One travels north to Federalsburg, where a scenic creek flows from the Idylwild Wildlife Management Area and winds through town. The other heads east toward the urban center of the region, Salisbury. History and culture mingle here with a pedestrianfriendly shopping plaza, a zoo, minor league baseball, and the Ward Museum of Wildfowl Art, featuring the world’s largest and finest collection of decorative and antique decoys. In Whitehaven, a rural village below Salisbury, the historic Whitehaven Ferry runs on the Wicomico River. Then, in Princess Anne, the 200-year-old, neoclassical Teackle Mansion rests among 300 Federal-style and Victorian structures.
Continue to Pocomoke City and the Delmarva Discovery Museum to explore how people’s lives have been shaped by the water and land. Get up-close with Diamondback Terrapins, Horseshoe Crabs, North American River Otters and more through hands-on exhibits about the Chesapeake’s habitats. Follow the byway to one of the southernmost spots in Maryland – Crisfield – famous for its local seafood, peaceful water trails and annual Hard Crab Derby. Kayak or canoe among towering loblolly pine forests and tidal marshes with sandy beaches at Janes Island State Park, a nature lover’s paradise. Cruises and ferries run from Crisfield to nearby Smith Island, Maryland’s only inhabited island accessible only by boat. Here visitors can see the Chesapeake watermen’s life in action at its docks, villages and at the Smith Island Crabmeat Coop. Don’t miss having a piece of Smith Island Cake, Maryland’s official state dessert.
