The Chester River is a tidal river on Maryland's Eastern Shore, a major tributary of the Chesapeake Bay. Its character varies significantly between its upper and lower sections. The upper river near Chestertown offers a more protected, historic, and town-based paddling experience. The river widens considerably downstream towards Rock Hall and the bay, where it becomes exposed to greater wind fetch and boat traffic, capable of generating good size waves. Paddlers should be aware this is a tidal waterway; planning around tides is essential, especially for routes like circumnavigating islands where timing can ensure a tide-assisted journey both ways. The river's diverse ecology supports over 200 species of birds, particularly around Eastern Neck Island, and bald eagles are commonly sighted near Buckingham Wharf.

Key access points include several public launches. In Chestertown, Wilmer Park provides a serene, picturesque riverfront launch with a gazebo and green space, while the Chestertown Marina offers a floating kayak launch and a boat ramp for a fee. Downriver, public boat ramps are available near the town of Chester and at Bayside Landing for accessing Rock Hall Harbor. Other noted put-ins include Cannon Street's floating dock, Bogles Wharf, and Eastern Neck National Wildlife Refuge. The best seasons for paddling are generally from spring through fall.

The area is steeped in colonial history, visible from the water. Paddlers can view one of the country's best-preserved colonial seaports from Cannon Street, pass the historical Millhouse in Millington, and explore Grays Inn Creek, an 18th-century shipyard site. The river near Chestertown features well-preserved Georgian-style architecture and brick sidewalks along its shore. Hazards primarily involve the open, lower river section, which is wide and exposed to winds, tides, and significant boat and ship traffic, making it challenging for inexperienced paddlers. It is recommended to stay out of the main Chesapeake Bay proper due to these conditions. Facilities vary by launch site but often include parking lots and boat ramps; some, like the marina, may charge a fee.