It's a well graded and efficient route, The old way, the road from Pomfret, across the Quinebaug to Thompson Hill and on to Douglas.

The westerly part of the route was "laid out" ca 1724 as a "road" from Hartford to New Roxbury (Woodstock). On that part of the route, just east of the Pine Hill (aka the Meeting House Hill) in Ashford, the old path branched, one way going on to Providence, the other leading to New Roxbury. The New Roxbury route branched, one way to Plaine Hill the other, this route to Thompson Hill.

Plaine Hill in Woodstock is near the site of Wabaquasett, a Shetucket/Wabawuasett town that John Eliot and Daniel Gookin visited in 1674. Thompson Hill is near the site of Quinnitasset, a 1674 Quinebaug or Nipmuck town.