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.
The old town is split by the canal into a north and a south side, each with Victorian houses, small shops, cafes and inns that look over the water. It is pleasant to walk, especially in the evening, when the lamps come on and the lock-keeper's old pump house, now a small museum, catches the light. A tall, arching bridge carries the road high over the canal, with a long view of the water and the countryside on both sides, and it is a good start to the ride.
From here, the byway heads south through the Upper Eastern Shore, a flat, quiet countryside of farm fields, tidal creeks, hedgerows and little towns. The roads are gentle and winding, with a good surface, mostly modest speeds, and plenty of places to pull over. You are never far from water, and the landscape changes with the season, from green fields in spring to golden stubble in autumn. Wildlife is part of the show, with herons, ospreys, geese and swans, and deer at dusk.
The town is small, with fewer than a thousand people, so for fuel head to Elkton, about nine kilometres away, where you will find stations and shops. In town, cafes and taverns serve Chesapeake favourites: crab cakes, steamed blue crabs seasoned with Old Bay, oysters in season, and cold beer. Summer is warm and humid, with biting insects near the marshes, and the best months for riding are May, June, September and October, when the air is cooler and the light softer. Weekday mornings are especially calm.