Chester is one of those Connecticut River towns that seems too small to have so much going for it. It sits on the west bank of the lower river, in the hills of Middlesex County, a few miles up from the Sound, and has a tidy village centre with a handful of good restaurants, a couple of galleries and a tiny theatre. It is a fraction of the size of East Haddam across the water, and quieter, which is why riders like it.
The roads around here are the draw. Route 148 and Route 154 run through wooded hills and past old farms, with hairpins and short rises where the glacial rock pokes through the soil. The river itself is broad and slow, and a ride along Route 82 on the east side, or the shaded lanes through Deep River and Essex, gives glimpses of the water through the trees. The Chester-Hadlyme Ferry, one of the oldest continuously operating ferries in the country, crosses the river nearby; it is a short and cheap way to get over the water, and a ride on it feels like stepping out of the twenty-first century for five minutes. It is a seasonal service, so check that it is running before you plan around it.
Just across the river on the Hadlyme side stands Gillette Castle, a strange stone mansion built in the 1910s by the actor William Gillette, famous for playing Sherlock Holmes on stage. Gillette designed the whole thing himself, with a model railway and trick door latches, and the state now runs it as a park. The grounds have a view over the river that is well worth a stop.
Nature along this part of the river is richer than you might expect. The tidal marshes and coves hold ospreys, herons and, in winter, bald eagles, and the Connecticut remains one of the cleaner large rivers of the Northeast. Autumn is the time for colour, but in late spring, when the dogwoods bloom and the shad run, the valley is lovely too.
For fuel, East Haddam, six kilometres away, is the larger town and a safe place to fill up, though Chester has a gas station on its main road. Parking in the village is easy off-season and tight on summer weekends, when the restaurants fill and the line for ice cream gets long.