Early Homesteads of Hampton & Pomfret
Not sure how or why I stumbled across that, but it made for an interesting (in a history geeky way) read.
By far my biggest discovery was about "the Old King's Highway" being the Nipmuc Trail...and it being Stetson Road. Now, these Indian trails were not a single route; North and South Bigelow Roads in Hampton undoubtedly formed an alternative route. It also made me think, "Why there?" till looking at a map I realized the route the authors described avoided major brooks and swamps.
While the trail led from Brookfield, Mass. (Quabog) to Norwich, Conn. the part I could follow best, starting on the south end of Canterbury went up Water Street, then crossing Route 14 followed Brooklyn Road -- the original path would have crossed at the corners with Colburn Road; but as the book detailed an innkeeper had bribed surveyors to move the road to east of the Westminster meetinghouse for commercial advantage. Colburn seems to form a reasonable alternate path, heading off towards South Bigelow and the Little River Valley as an alternate place for the Indian villages that moved every 10 years or so.
Crossing into Brooklyn it becomes Stetson Road, then Cherry Hill, then in Pomfret Brooklyn Road, and then Page Road but not coming back to Brooklyn Road as Page Road currently does but continued north (along a right of way still visible in property maps) to Duffy Road which joins Route 97 at the south end of what was originally the Abington commons.
Continuing north on 97, there seems to be a couple reasonable alternatives -- on followed Taft Pond Road to Dennis Road and (by the abandoned part of Dennis which comes out near or is the driveway to the 4H camp) back to Taft Pond to Ragged Hill and Swedentown Roads and then by abandoned road to the intersection of Perrin and Rocky Hill Roads, Rocky Hill likely one of the alternative routes of the Old Connecticut Path.
The other by North & Angell Roads to end up near Quassett Lake and the major Indian village of Wabbaquasset (South Woodstock).
From here it seems to me most logical for it follow the Old Connecticut Path until crossing the Quinebaug River around Fabayan or Quinebaug, and then it would be a straight shot up today's Route 31 (again avoiding all major water crossings after the Quinebaug) to meet the Bay Path in Charlton and head west to the north side of Quabog Plantation in the Brookfields.
The Homesteads book, however, mentions it crossing the Quinebaug in the Sturbridge area -- perhaps this was the alternate route to get to the south side of Quabog, and/or the route best suited to Nipmucs inhabiting the area around Mashapaug (Bigelow Hollow). Trying to avoid crossing the Quinebaug would have required a quite difficult detour crossing many of the strong SW-to-NE running ridges near Mashapaug and at times heading south before turning west only to have to turn back north then east again to reach Quabog.
The final speculative thought is all these "Old King's Highways" that clearly were not (English) Royal roads; but could this be related, even in a tongue and cheek way by early settlers, to use of "King" in lieu of Sachem, e.g. King Phillip's War?