Putnam as a town has been seriously incommoded by the uncertain tenure of its roads. It has been exceedingly difficult to trace the roads of three distinct towns to their original layout. In several cases it has been made evident that there was no layout, but that in confirmation of the modern development theory the roads were slowly evolved from Indian trails and “trod out paths. This is very notably true of the original east side road, between the tipper and High Falls, which must have existed as a trail or mode of communication from time immemorial. The road west side of the river was made, as we have seen, by order of the town of Woodstock, about 1700, crossing Mill river or Muddy brook just below Peter’s brook, and thence southeast diagonally over the falls, past the old Killingly burying ground, and onward around the base of Killingly hill. In the deed describing Deacon Eaton’s farm west of the Quinebaug, the Providence road, it is said ” crosseth its southeast corner,” and another road passed through his land, “formerly laid out from Hartford to Mendon.” This road, laid out before 1700, must have run nearly north up the Quinebaug valley and connected with what was known as the Old Connecticut Path at the crossing below the site of the present New Boston, but it was probably not a common thoroughfare, as we find no other trace of it. It is altogether probable that there was a ” trod out ” road east of the river also, extending south to Plainfield and Norwich. As a matter of fact, we know that there has been such a valley road as far back as can be traced, that the first surveyors of this wilderness land found away to get there, and that a rude track had been trodden out and made passable before the actual settlement.
In consequence of the total lack of record of “Town Acts” in Killingly for more than twenty years after its organization, we are left in ignorance of its first attempts at road making. The country road, as it was called, leading from Plainfield to Boston, laid out by government before 1700, passed through Killingly, and was nearly identical with the north and south. road now passing through the same section. It has been twice re-surveyed and laid out, but no change has been made in its general bearings. The first surveyors found it easier to run their line west of Killingly hill, but in the “perambulation of 1731 ” the road was made to ascend “to a heap of stones on a rock upon the hill,” and so on over its summit. In 1721 a cart path from Pomfret to Providence was opened under the supervision of Nathaniel Sessions, crossing the Quinebaug over Sabin’s bridge, and thence over the former road cut through by Aspinwall, making it passable for wheeled vehicles. The above roads are all that can be identified prior to the establishment of Howe’s mills. Efforts were then made to increase accommodations. A private road or bridle path leading from the bridge to Perrin’s farm and the Gary district was improved and made a public highway, and a bridge thrown over -Mill river in 1732.
Sabin’s bridge was reconstructed or thoroughly repaired by Samuel Cutler, a distant relative of Captain Isaac Cutler, who was now living at the north end of Killingly hill., He then petitioned the general court for forgiveness of country rates, license to keep a place of public entertainment, and for a committee to lay out a road from Sabin’s bridge over Killingly hill, past his dwelling, at a place called ” The Four-fanged Oak,” and eastward to intersect with the Providence road, thereby preventing the long journey round the base of the hill. This new road he averred would be a great convenience to travellers, and indeed was “now travelled on but not yet laid out.” His requests were all refused, but undiscouraged he applied to the town authorities, who in August, 1732, warned a meeting “to consider of altering the country road that goes through the town towards Providence at the west end, in order to meet a road laid out by the town of Pomfret, at David Howe’s mills.” The town voted not to alter the road,” and thus it happens that the road leading from Putnam to the north end of the Heights, was left to evolve itself, not having been laid out by lawful powers. This persistent refusal may have been caused by the fact that “Sam Cutler ” was not considered as sound as some of his neighbors and was inclined to speculation. He succeeded in obtaining release from rates for his services upon the bridge, but the Fourfanged Oak Tavern ” and highway passing thereby were not granted.
The petition of those honored town fathers, Captain, Joseph Cady and Jonathan Eaton, for a better road to Thompson meeting house, met a very different reception. A committee was at once appointed to consider their needs and those of other church-goers. In point of fact they did little more than to establish roads already existing in a crude form, the town having voted that every person that shall move to this town to have any way altered or removed, it shall be done at the petitioners’ cost and charge.” September 12th, 1737, the committee reported a road laid out, ” beginning east end of the bridge over the Quinebaug, near Mr. David Howe’s, thence extending along the path or road, leading from said bridge to Captain Cady’s; thence northeast by pine trees and great rock, east of an old ditch in Mr. Simon Bryant’s land, to a corner between Bryant’s and Wil-liam Larned’s, thence in the same corner to the southeast corner of Larned’s fence, keeping the path leading thence to John Lee’s; thence to the brow of a hill of Deacon Eaton’s land; thence over Hosmer’s field into the road to Thompson meeting house,” near the site of the present residence of Mr. George H. Nichols. This connection with the West Thompson road instead of the direct road from Killingly hill to Thompson, is an indirect testimony to the existence of the valley road previously referred to as passing near Deacon Eaton’s. Hosmer owned land now in the vicinity of Mechanicsville. The road from Captain Cady’s, ” as trod,” winding back nearly to the river, so as to accommodate William Larned, John Lee and. Deacon Eaton, must have been laid nearly in the form of a horse shoe.
A bridle road with gates and bars was also allowed ” as the path is trod” from Jonathan Hughes, near the country road, past the dwelling houses of John Pepper and Phinehas Lee to William Larned’s; also a bridle road from “land of Simon Bryant to the country road from Plainfield to Oxford, upon the path on which said Bryant usually travelleth from his own door to Thompson Meeting House.” This bridle road is probably identical with the present road passing Dr. Holland’s residence. The rapid growth of this neighborhood and the need of open access to Howe’s mills transformed the first named bridle road in a few years. ” March 4th, 1749, Voted, to allow and accept an open road from Capt. Daniels’ bridge as the road is now trod along by William Larned’s house and by Phinehas Lee’s and Mr. Gay’s, &c., into the country road by Edmond Hughes’, three rods wide, excepting through Mr. Gay’s land, where there is now a stone wall on both sides, and there it is to be but two rods wide, and if the wall must be moved to make it two rods wide the surveyors that mend the road are to move the wall, and it is to be understood that the men that own the land where the road is allowed and accepted appeared in the meeting and there declared that they would give the land for the said road two rods wide as is above mentioned, and the road was allowed and accepted upon those terms.” This is the ancient road now passing over Parks hill and winding round to the brook near Mr. Olney’s, and the moss-covered walls now tumbling into ruin are the same that Mr. Lusher Gay refused to remove in 1749.
Source: History of Windham County, Connecticut, Bayles, Richard M.; New York: W.W. Preston, 1889Home » Windham County » History of Roads in Putnam, Connecticut