Chesapeake Country Scenic Byway

Scenic road chapters

Waypoint introductions and full write-ups

1. 1. Chesapeake City

   Chesapeake City is a tiny, tidy canal town on the Maryland shore, in the narrow neck of land between the Chesapeake Bay and the Delaware River, and it exists because someone had the idea of cutting a channel across the peninsula. The Chesapeake and Delaware Canal, opened in 1829, links the two waterways, saving ships a long voyage down the bay and around Cape Henlopen. It was enlarged and straightened in the twentieth century, and still carries a great deal of shipping, so the sight of a huge container ship gliding past the end of a village street is normal here.

   Read the complete Chesapeake City write-up.

   Recorded stop-planning note

   May refer to an earlier itinerary; verify against your selected route before riding.

   Planning note

   Chesapeake City is where the day begins. Next is Chestertown.

2. 2. Chestertown

   Chestertown looks like a town that decided long ago what it wanted to be and then very sensibly never changed its mind. It sits on the Chester River on Maryland's Eastern Shore, at the head of navigation, and its old brick houses, many from the eighteenth century, still line the streets leading up from the waterfront. The place was a colonial port, shipping tobacco and grain to Europe, and the wealth that built those handsome Georgian merchants' homes is still visible in the cornices and doorways.

   Read the complete Chestertown write-up.

   Recorded stop-planning note

   May refer to an earlier itinerary; verify against your selected route before riding.

   Planning note

   Chestertown comes up about 48 km into the recorded legs. Next is Rock Hall.

3. 3. Rock Hall

   Rock Hall is a working harbour town first and a tourist stop a distant second, and it likes things that way. It sits on the Chesapeake Bay side of Maryland's Kent County, a short, low-lying run west from Chestertown, and the waterfront is where the town keeps its heart: crab boats, oyster boats, marina slips, and the weathered sheds that go with them. The local people are watermen, and the town has long called itself a place for fishing and boats. Pearl of the Chesapeake is the line you will see on the signs.

   Read the complete Rock Hall write-up.

   Recorded stop-planning note

   May refer to an earlier itinerary; verify against your selected route before riding.

   Planning note

   about 69 km into the recorded legs you reach Rock Hall. Next is Easton Maryland.

4. 4. Easton Maryland

   Easton is the county seat of Talbot County and the unofficial capital of Maryland's Eastern Shore, a handsome town of about seventeen thousand people on the flat, creek-slashed land between the Chesapeake Bay and the Choptank River. It is a place of brick courthouses, tree-lined streets, galleries and boutiques, and an old hotel on the main street, and it has an air of quiet prosperity. For a rider at the end of a day, it is a comfortable place to get off the bike and find a good meal.

   Read the complete Easton Maryland write-up.

   Recorded stop-planning note

   May refer to an earlier itinerary; verify against your selected route before riding.

   Planning note

   Easton Maryland closes the day.