The Chester River flows through Queen Anne’s County. Photo by Will Parson/Chesapeake Bay Program with aerial support by LightHawk.
A rower scoots along the still waters of the Chester River at dawn.
The Chester River harbors colonial history, quaint towns, natural resources, and recreational opportunities
Forty-two rivers crisscross Maryland. The Chester River on our state’s Eastern Shore is one of them. For 43 miles, it flows through Kent and Queen Anne’s counties’ prosperous farmland, beginning near the town of Millington and widening to three miles at its confluence with the Chesapeake Bay. It is a river rich with fish, wild game, and, at one time, oysters, which attracted Native Americans to the region for thousands of years. Signs of their villages can be seen in oyster middens emerging from ancient shorelines. Thankfully 2,300 acres of the ecosystem on the river’s southern end are untouched and protected as the Eastern Neck National Wildlife Refuge sanctuary for migratory birds.
In 1670, however, along Grays Inn Creek on Eastern Neck, one of 30 creeks that feed into the Chester, two colonists, James Ringgold and Samuel Tovey, laid out the first planned town in the New World. A courthouse and other public buildings became New Yarmouth, but tobacco harvests from surrounding farmland demanded better river access and encouraged a new town to be built along the Chester.
The new town would be founded in 1706 as Chestertown, a Royal Port of Entry, and government seat of Kent County. The town grew quickly as four years of tax freedom was promised to skilled artisans. A center for planter merchants and a harbor busy with sloops and schooners fueled a wealthy populous, who built magnificent homes along the waterfront. These homes are visible today in one of the best-preserved colonial seaports.
Prior to the American Revolutionary War, Chestertown also staged a tea party revolt. The town was also an important gathering place for national leaders from Virginia and Maryland moving by ferry from Annapolis across the Chesapeake Bay to Rock Hall, en route to Continental Congress meetings in Philadelphia. It was the route followed by Tench Tilghman to announce Cornwall’s surrender in the 1781 Battle of Yorktown. A replica of a Royal Navy 1768 schooner, The Sultana, that patrolled the river coastline during the war years, sits in the harbor today; a center for storytelling and educating 5,000 students annually on the years of struggle for a new nation. In 1789, Washington College was founded by and named for America’s new president.
Upriver from Chestertown is the town of Crumpton. It too was a port town and a mill town serving the grain farmers. Here, Henry Callister, an indentured servant, ran a ferry across the narrowing river in 1753. Later, the steamboats, including Dreamland, known as the fastest boat on the Bay, would carry passengers to Crumpton, a center for peach harvests. But when the peaches developed a fungus and died, steamboats stopped running to the town, and by 1923, Crumpton slowed down its wild ways. Then, famously, Crumpton began its open-air antique markets and auctions, which replaced the peach orchards. Though the covid pandemic recently shut down the energized bidding on antiques, this year there has been 25 auctions scheduled—a welcome return for patrons.
Further upriver, Millington is as far as one can navigate the Chester. A village of 549 souls (just 200 more than its 1860 population) houses the John Embert farm, identified as a historic site built in 1800 and described as an “exceedingly rare and almost pristine example of a small-scale Tidewater house.”
1: Chestertown dock at dusk with boats, including the Schooner Sultana. 2: Historic estates of Chestertown, some of which date back to the colonial period, line the waterfront. 3: Fanels Branch, a tributary of the Chester River, is bordered by a mature riparian forest buffer separating the water from surrounding farmland in Kent County. Photo by Will Parson/Chesapeake Bay Program with aerial support by LightHawk. 4: The Chester River wraps around Eastern Neck National Wildlife Refuge in Kent County, Maryland. Photo by Will Parson/Chesapeake Bay Program. 5: Birdwatching is a popular activity at Eastern Neck National Wildlife Refuge.
That the Chester is home to many historic structures is not surprising. It enters the Chesapeake Bay on the northern boundary of Kent Island—the 31-square-mile island is the largest in the Bay. Settled in 1631, it is the original colonies’ third oldest permanent settlement, after Plymouth, Massachusetts, and Jamestown, Virginia. Captain John Smith, who charted 3,000 miles of waters around the Chesapeake Bay, noted Eastern Bay and the mouth of the Chester. Today, the Capt. John Smith Chesapeake National Water Trail, under the direction of the National Park System, follows his journey of discovery.
Kayakers and canoers can explore 100 miles of water trails along the Chester from its mouth at Love Point (once a hotel jumping off point for a train to Ocean City), up its many creeks or toward the Corsica River at Centreville. Interested water trail buffs can book guided water tours or put in at sites identified in maps by the Maryland Department of Natural Resources. Walking trails also parallel the river. The Wayne Gilchrist Trail, named in honor of the local congressman and environmentalist, follows an old railway through Chestertown to Washington College. And the Eastern Neck preserve includes a 10-mile circumference water trail, as well as walking boardwalks to view the wildlife it protects.
In nearby Rock Hall, watermen focus on plentiful fish and crabs, supplying many of the local restaurants that offer the bounty of the bay and the river for all to enjoy. The diversity of ecosystems that Native Americans enjoyed is still in place along the historic Chester River. It is a river enjoyed for leisure and for those who make their living on the water. It is a river with many stories to tell about the people that settled along its shoreline. It is a river to be enjoyed.
