Ask anyone in Winsted about the summer of 1955 and you will get a story. In August that year two hurricanes in quick succession dumped rain on northwest Connecticut, the Mad River overflowed its banks, and the flood tore through the center of town, taking out much of Main Street. The town rebuilt, and today the downtown is a plain, practical place with a few handsome brick blocks, a long lake called Highland Lake on its northern edge, and a settled, hill-country feel that has little to do with tourism.
Winsted's claim to wider fame is a man who made a career out of asking awkward questions. Ralph Nader, the consumer advocate, was born here in 1934, and the town's name sometimes surfaces in stories about his early life. More relevant to a rider is the reservoir. A few miles southeast, the Saville Dam, finished in 1940, holds back the West Branch of the Farmington River as the Barkhamsted Reservoir, a big, sinuous sheet of water that supplies Hartford and its suburbs. The road along the shore keeps close to the water, and the surrounding forest, much of it state land, keeps the shoreline free of houses.
The riding around here is quietly excellent. Route 20 and Route 318 run through rolling woods, with long, smooth curves and gentle climbs, and the reservoir views open up in a few places. Further on, Riverton has a small village of white houses, a general store and the old chair factory associated with Lambert Hitchcock, whose painted, stenciled chairs became known across America. The Farmington River is a well-known trout stream, and in summer the pull-offs have fishermen standing knee-deep in the current.
Winsted has fuel, supermarkets and several diners, and it is the best place to stock up before the quieter hills. Autumn is the headline season, but late spring is a pleasure, with high water in the river and fresh green on every slope. Keep an eye out for deer, especially around the dam where woods meet the road, and be careful on the shady sections early in the year, when patches of ice linger well into April.