Perhaps the most serious inconvenience resulting from the unorganized condition of the future Thompson was inability to provide suitable roads. To make a good road in its hard and rockbound soil was a very difficult enterprise, requiring the authority of selectmen or suitable officers. Lacking such authority, the settlers simply “trod out ” their own ways from house to house, and to such points as enabled them to communicate with the outer world. For public roads there was the “old Connecticut Path,” obliquely crossing from Massachusetts line into Woodstock, below the site of the present New Boston. There was also the road from Plainfield, a wretched “old gangway,” as it was sometimes called, very nearly corresponding with the present north and south road through the town. The entire lack of all other accommodations may be gathered from the universal cry that arose from all sections simultaneously, for ” roads to Thompson meeting house ” when that edifice was opened for public worship. They seemed demanded not merely as a matter of convenience, but out of respect to the day and occasion. Homemade, trodden-out paths might answer for going to mill and visiting neighbors, but a special “go-to-meeting” road seemed as indispensable as Sunday clothes. The only apparent use for a road was to travel to Thompson meeting house ” upon; at least no other object was hinted at in the numerous petitions with which Killingly was deluged. The selectmen of this town, only too happy to exercise authority over this coveted section, appointed a committee in 1730 to go to the parish of Thompson and to take a view and see what ways they need to go to their meeting house, and layout what they think best, modifying this order by the subsequent vote-” That for the future every person that shall move to this town to have any way altered or removed, it shall be done at the petitioner’s cost and charge.” So arduous was the task laid upon the committee, so large the number of roads demanded, and so difficult of manufacture, that it seemed quite unable to grapple with it, and in the great majority of cases simply confirmed the roads “as trod out,” or made slight alterations and improvements. Among the roads thus altered was the one ” beginning west side of Quinebaug River, near Mrs. Dresser’s, and on between Captain Howe’s house and barn to the French River . . . and so as the road is now trod to ye meeting house “-varying little from the present road to West Thompson.
The road from ” Sabin’s Bridge ” (now Putnam Centre) was a very remarkable achievement, accommodating Joseph Cady, Deacon Eaton and other widely separated prominent citizens, and also contriving to intersect ” the path by which Simon Bryant already traveleth from his own dwelling house to Thompson meeting house.” Still more remarkable was a road laid out by a special committee ” chosen to view y e circumstances in ye quarter of ye Greens,” which, starting from Thomas Whitmore’s corner (now Whittlesy’s, Putnam), meandered leisurely about Pattaquatic, from Bloss’s pasture alongside of a brook to an oak near Phinehas Green’s house, thence to another oak in Henry Green’s pasture, crossing and recrossing the stream at lower and upper fordways, and after accommodating all the families of that section, wound through Merrill’s improved land “into the old road over quinnatisset Brook, and so as the road goes till it comes into the country road, southwest corner of Hezekiah Sabin’s little orchard, foreside of the meeting house.” This very ancient road, “old ” in 1735, is still extant and in good condition, forming the southern side of that nondescript geometrical conformation east of the village of Thompson called by courtesy “The Square.” A venerable Seakonk sweeting and one or two Roxbury russets are the sole survivors of this primitive orchard. One of the ways left ” as trod,” to evolve itself in time into a passable cart road, was one demanded by Hascall, near the Massachusetts line, who had to let down twelve pairs of bars on his way to meeting. The condition of the road over which Samuel florris was required to travel to that distant shrine will be best described by himself in another place. Among old roads still in use is what is called the “Mountain Road” to Putnam, which was laid out in 1763. To this very irregular and inconvenient style of roadmaking the present residents of Thompson are indebted for the number and variety of rural, romantic, roundabout drives for which it is distinguished, dating back to those old days when every household in town had a special way of its own.
The problem of bridge-making weighed very heavily upon the early settlers of Windham county. To construct a bridge that could withstand the swollen current of the raging Quinebaug, whose ravages it was declared ” could not be paralleled in the colony,” seemed beyond human attainment. Again and again bridges were constructed at great cost and labor, only to be swept away in a few months. Yet, in the face of all this discouragement, Mr. Samuel Morris contrived to build a bridge over the Quinebaug at his settlement, in 1717, which did good service for many years. No wonder that his Indian followers looked upon him as almost a supernatural power, and that the general assembly should exempt him from “paying any rates whatever ” for the term of ten years. In 1722 a cart bridge was built over the Quinebaug by Sampson Howe and John Dwight, upon the road over which the latter afterward traveled to meeting a good bridge and great convenience to the public; but as a bridge had just been built below the High falls by Captain Sabin, with assistance from government, these builders were obliged to pay their own expenses. In process of time all the more traveled roads were supplied with bridges. A bridge was built over the French river by Henry Ellithorpe, on the present site of Grosvenor Dale, which bore his name for many years.
Source: History of Windham County, Connecticut, Bayles, Richard M.; New York: W.W. Preston, 1889