New Milford is big in a way that surprises people: it is the largest town in Connecticut by area, spread across both banks of the Housatonic River with a long green at its center. That green is the heart of it, a classic New England common lined with churches and old houses, and the place to start a loop into the Litchfield Hills. You get a real town here, not a museum piece, with working shops and the usual stations and diners you will want before heading north.
The Housatonic is the thread that ties the ride together. It runs south through a valley that is more rugged than most people expect of Connecticut, with wooded ridges on both sides and a few old iron bridges. North of town, Route 7 follows the river toward Kent and Falls Village, one of the nicest valley roads in the state, with gentle curves, farm stands and the occasional glimpse of white water. The Appalachian Trail, on its way to Maine, crosses the river near Kent, so on a fine weekend you will see hikers with big packs walking the road shoulder.
Close to town, look for Lover's Leap, where an iron bridge spans a narrow gorge on the river. The legend attached to it, a Native American princess who leapt to her death for love, is typical of the romantic stories New England attached to its rock faces in the nineteenth century, and the gorge itself is real and a pleasure to see. The river is dammed upstream and down to form Lake Lillinonah, whose shores add a series of wooded coves to the scenery. A little west of here, Candlewood Lake is the largest lake in Connecticut, built in the 1920s for power generation.
For riders, the best months are May, when the dogwoods bloom, and October, when the hills go copper and gold. Summer is busy but fine early in the day. Fuel in New Milford is no problem, and Sherman and Washington to the north and west have smaller stores. Deer are a constant hazard at dusk, so keep an eye on the verges, especially on the quieter back lanes where trees crowd the edge of the tarmac.