The Litchfield–South Roads Historic District encompasses part of the traditional town center of Harwinton, Connecticut.

The town remained agricultural through the 19th century, its economy not industrialized due to a lack of railroad connections and suitable water resources.

In the early 20th century, it joined the trend of other communities in northwestern Connecticut in the rise of second homes for city dwellers.

One of these, William McConway of Pittsburgh, Pennsylvania, had a series of fine quarry-stone walls built along South Road.

There are four churches in the district, as well as the site of the town's first cemetery and meetinghouse; the latter was set directly in the central junction.