Made up of two villages and a varying landscape that includes floodplains, wetlands, fields, and mountain slopes, Sheffield is practically the postcard for bucolic New England towns. It’s the oldest town in the county, founded in 1724, and sticks close to its agricultural roots. Only 2.5 hours from New York City, it’s a favorite of second-home owners and professionals who frequently commute in to the city. Sheffield has a small business district, as well as a growing arts scene. It’s also widely known as one of the hottest antiquing spots in the area.