Pete Salomone suggested this as one of the best cycling loops in northwestern Connecticut. The ride originates in Pleasant Valley near Winsted CT, at Peoples StateForest. It start out along the river for a short distance, then continues across the Massachusetts state line to Sandisfield State Forest. There are 2900 ft. of climb over 45 miles; the climb is gradual and consistent at the beginning, with some nice steady downhill riding at the end, but not too many descents and re-climbs.
There are excellent baked goods at Colebrook General Store (off route 1 mi south of Sandy Brook Rd on CT183) and at the Planted Feather Bakery 200 yards north of Sandy Brook Rd on CT 8. You can easily shorten this route by going to Colebrook General Store and back down Sandy Brook Rd.