Help stop the spread of COVID-19 and follow all current directives from your governor and local health officials about wearing face masks and physical distancing.

Explore the Chester River

The Chester River Water Trail

From the headwaters in Delaware to the river’s mouth between Kent Island and Rock Hall, the Chester River Water Trail encompasses more than 100 miles of waterways, a variety of ecosystems, and over 10,000 years of human history. The navigable portion of the Chester River begins near the town of Millington, Maryland, where the river is heavily wooded, narrow, and winding. After reaching the small town of Crumpton, the scenery transitions from woodlands to large waterfront farms. The lower Chester River near Rock Hall is over three miles wide and features excellent crabbing, fishing, sailing, boating, and scenic views. Paddlers in canoes and kayaks can explore numerous tidal creeks entering the river which contain pristine wetland habitats and abundant wildlife.

American Indians on the Chester

Prior to the arrival of European settlers, American Indians inhabited the waters of the Chester River for over 10,000 years. The river was teeming with fish, oysters, waterfowl, wild game, and edible wetland plants that provided all of the food needed to establish thriving communities. Settlements were generally located at the heads of creeks or springs, with populations ranging from a few families to several hundred residents. Ancient oyster middens, or trash piles, can still be seen eroding from the riverbanks where these American Indian settlements once stood.

John Smith Visits the Chester 

During his exploration of the Chesapeake Bay in August 1608, Captain John Smith visited an American Indian community at the mouth of the Chester River which he referred to as “Ozinies.” This site was most likely located in the vicinity of present-day Rock Hall. Smith did not travel up the Chester River’s main stem, in part because the river offered little promise of providing the elusive “Northwest Passage” to the riches of the Orient. However, Smith did chart the river’s mouth, Kent Island, and the forested interior of what would become Kent and Queen Anne’s counties.

Eastern Neck Island and the Eastern Neck Island Water Trail

Approximately ten miles south of Rock Hall lies Eastern Neck Island National Wildlife Refuge, a 2,285-acre preserve that serves as an important stop for thousands of migratory waterfowl each year. The refuge’s nine miles of roads and trails offer tremendous opportunities for nature viewing and bird watching. Water access can be found at Bogles Wharf Landing, where paddlers and recreational boaters can explore the unspoiled marshes of Eastern Neck Island. Bogles Wharf is also the starting point of the Eastern Neck Island Water Trail, a 10-mile trail that circumnavigates the island. 


The Chester River is home to a significant population of working watermen. On the lower river, most watermen run trotlines for crabs in the warmer months and hand-tong for oysters in late fall and winter. On the upper river, pound nets are used to harvest striped bass, white perch, and channel catfish. Communities with significant populations of watermen include Rock Hall, Kent Island, Queenstown, Centreville, and Quaker Neck.

Rock Hall

Rock Hall’s location at the mouth of the Chester River made it an important ferry landing for colonists traveling north and south in the 18th century, including George Washington. Today, Rock Hall is a haven for working watermen and a busy hub for recreational boating, with several marinas and three public landings within the harbor. The town is also known for its numerous festivals including Waterman’s Day, 4th of July Weekend, Fall Fest, and Pirates and Wenches Fantasy Weekend.


Founded in 1706 as one of six original Royal Ports of Entry, Chestertown is one of the best preserved colonial seaports in the United States. In the latter half of the 18th century, grain shortages in Europe allowed Chestertown’s merchants to ship local foodstuff s abroad for tremendous profits. The grandiose brick mansions they constructed still line the river today. In the 21st century, Chestertown’s scenic waterfront, brick-lined streets, and plentiful shops make it a popular tourist destination.


Located approximately ten miles from the mouth of the Chester River, Queenstown served as an important center for commerce in the 17th and 18th centuries. Queenstown is also home to Bowlingly, one of the oldest properties in the region which traces its history back to 1658. The port was the target of a raiding party during the War of 1812, when British troops under Sir Charles James Napier landed on August 2, 1813, skirmishes with the local militia, and seriously damaged the manor home at Bowlingly before returning to their ships.


The Chester River once contained some of the most prolific oystering grounds on the Chesapeake Bay, even att racing its own fleet of “oyster pirates” that regularly sailed under the cover of darkness to illegally dredge oysters reserved for hand-tonging. While much of the Chester’s oyster population has been lost due to pollution, overharvesting, and disease, the middle portion of the river contains one of the last viable oyster bars on the upper Bay. In late fall, watermen can still be seen anchored over this bar in front of Cliff City Landing using the ancient method of hand-tonging to capture the tasty bivalves.

Schooner Sultana

Constructed by professional shipwrights and volunteers in Chestertown, Maryland, the schooner Sultana is a full-scale reproduction of a 1768 topsail schooner used historically to enforce British taxes in colonial waters in the years preceding the American Revolution. The modern Sultana regularly plies the waters of the Chester River, providing educational programs to 5,000 students each year focusing on colonial history and environmental science.

Chesapeake Exploration Center

Located on Kent Island in the town of Chester along one of the major routes for traveling to the Eastern Shore, the Chesapeake Exploration Center (CEC) helps visitors discover the many sites to visit in the region. CEC staff can assist visitors with directions, information, and visitor services. The CEC also includes several exhibits on Eastern Shore heritage, serves as a hub for the Cross Island Trail, and is home to the skipjack Anna McGarvey. 

Kelsey Everett

Kelsey is the Digital Resouces Associate working with both the Chesapeake Conservancy and the National Park Service Chesapeake Bay Office. Previously, Kelsey held a Chesapeake Conservation Corps internship with the National Park Service. She is a graduate of University of Maryland, Baltimore County and holds a Bachelors of Science in Environmental Science and Geography.

May 7, 2016

Main image:
Older Newer