The Middletown Rural Historic District encompasses an area that was once the town center of Grafton, Vermont.

The area is now largely rural, with a small cluster of buildings at the corner of Middletown and Woodchuck Hill Road.

[2] The district extends along most of the length of Middletown Road, between Grafton Village and its northern end at Vermont Route 121.

Most of the houses in the district are wood-frame structures, in either Federal or Greek Revival style, with three examples of brick construction.

The old town pound, its stone walls dating to about 1808, is near the cemetery, and an 1856 schoolhouse stands at the junction of Middletown Road with Route 121, marking the northernmost end of the district.