The Upper Eastern Shore section of the byway begins in Chesapeake City, a town located at the western end of the Chesapeake and Delaware Canal. The byway heads south on MD 213, coming to Cecilton, where MD 282 heads west to Crystal Beach on the Elk River. The road crosses the Sassafras River and passes through Georgetown, a community that was burned by the British during the War of 1812. The Chesapeake Country Scenic Byway continues along MD 213 through Galena and Kennedyville, with a detour along MD 298 and MD 292 serving the Victorian resort town of Betterton. The mainline of the byway comes to Chestertown, a port on the Chester River that has many historical buildings. At this point, a branch of the byway continues west along MD 20 to Rock Hall, a town on the Chesapeake Bay with many marinas, before following MD 445 to the Eastern Neck National Wildlife Refuge. From Chestertown, the mainline of the Chesapeake Country Scenic Byway continues along MD 213 to Church Hill, where St. Luke's Episcopal Church and Church Hill Theatre are located. The next town along the road is Centreville, which is home to the Museum of Eastern Shore Life and the Queen Anne's County Courthouse, the oldest active courthouse in Maryland. From Centreville, the byway follows MD 18 west to Queenstown, which has many Colonial buildings, and Grasonville. The road heads onto Kent Island, an island where a trading post was founded in 1631 that has many seafood restaurants. The Chesapeake Country Scenic Byway comes to Stevensville, which is home to the Cray House and the Stevensville Train Depot. At this point, a connection for the byway crosses the Chesapeake Bay Bridge to Annapolis.