One of the first needs that Pomfret felt after the meeting house had been built, was for a way to get to it. Roads were not laid out at the start and the attention of the people was now turned toward this deficiency. Within the bounds of the purchase, which covered more than half the territory of the town, it belonged to the proprietors to provide them, but outside of those limits it belonged to the town. This arrangement was not satisfactory, as harmony of action was not always attainable. The proprietors, at a meeting in March, 1726, agreed to make over to the town all highways in the purchase. The town then went forward with the work of making roads and bridges as occasion and circumstances required. In 1731 a substantial cart bridge was built over the Mashamoquet at the saw mill, and a highway was laid out from it to Windham village. In 1788 a new road was laid out to Ashford, beginning “at a small fall in Mashamoquet brook, thirty rods below the old going-over to Ashford.”
In 1770, Pomfret joined with Killingly in rebuilding what was known as “Danielson’s bridge.” In the following year, “Cargill’s bridge” was rebuilt. Putnam was foremost in a movement for procuring a new road through Pomfret to Norwich and New Haven, but failed to secure it. Notwithstanding all the pains taken to secure easy communication with Providence, rendered so needful by intimate business and social relations, the road thither was still very stony and rough, and the journey laborious. So late as 1776, when Mr. S. Thurber drove over it in the first chaise, he ” could not ride out of a slow walk but very little of the way, and was near two clays in going.” Pomfret was much interested in a project for deepening the channel of the Quinebaug, so as to make it passable for boats, Ebenezer and John Grosvenor petitioning with citizens of other towns for this object. One of the first dams upon the Quinebaug was accomplished by Jabez Allen, near the mouth of Beaver’s brook, about 1770. A large grist mill was here erected by him and carried on successfully for a few years. The laying out a public highway from Pomfret street to Cargill’s mills gave the town a great deal of trouble. After the rejection of many proposed routes, the road ” from Little bridge that crosses Mill river, leading to nigh the dwelling-house of Mr. Abraham Perrin,” was established and recorded, May 14th, 1798. It was also voted to rebuild Mill River bridge and repair Cargill’s bridge.
In the early part of the present century Pomfret was greatly agitated by the proposed construction of various turnpike roads through her territory. Progressive spirits favored these enterprises, but the heavy outlay and prospective imposts terrified a majority of the tax payers. At the first proposal “to lay out a road from Hartford towards Boston to the Massachusetts or Rhode Island line,” the town appointed Colonel Lemuel Grosvenor, Lemuel Ingalls, Esq., and Captain Josiah Sabin, to make such preparations for surveying as would be necessary for information, and to wait upon the committees sent by the general court. In December, the town deferred acting upon raising money to pay assessments to individuals for road laid by state committee, and appointed Peter Chandler, Seth and Joshua Grosvenor to confer with neighboring towns respecting laying out a road from Hartford to Douglass, and for preparing a memorial for alteration of road or repeal of act. In the following year the town refused to raise money to pay assessments to the persons who waited upon them. NV hen, in spite of their grumbling and resistance, the Boston and Hartford turnpike was actually completed through the -whole length of the town, Lemuel Ingalls and Seth Grosvenor were appointed to have it altered in certain points and the expense lessened. All efforts proving unsuccessful, the town was reluctantly compelled to levy a tax of three and a half cents to meet expenses and pay assessments, but declined to accept shares in the company or to allow Captain Sabin for attendance upon the committee. Projects for a new road in the west part of the town through Joseph Sharpe’s land to Brooklyn, and for two other turnpikes, increased the town’s ill humor. They would not view the different routes through Killingly nor do anything about it, and appointed agents to oppose the memorial of Sampson Howe and others, and also acceptance of a road laid out through Pomfret from Norwich to Massachusetts line, but were again obliged “to raise money to pay assessments made by state committee for said road.” The Pomfret and Killingly turnpike was also carried through after much opposition and refusing to pay the cost of the jury that laid it, and in 1803, it agreed to build a bridge in company with the town of Killingly over Quinebaug river, south of Noah Perrin’s-Caleb Trowbridge, Benjamin Durkee and Freeman James to build said bridge. It also voted to build a bridge across the stream near the burying ground, and also one on Mashamoquet “where the turnpike crosseth it w. here old road is discontinued.” So great was the outlay caused by all these turnpikes and bridges that it was proposed to sell the newly constructed town house. Before accounts were settled another turnpike was demanded-a direct road from Providence to meet the Boston and Hartford turnpike in Ashford. Oliver Grosvenor and Sylvanus Backus were at once empowered to oppose this farther imposition. Surveys were, however, made and two routes offered for consideration. In 1806 the town voted that the north route by Samuel White’s to Cotton’s bridge would best accommodate town and public, and to oppose the route from said White’s to the Landing, but as in previous cases they were forced to submit to road and taxes.
A new road was laid out to the Brick Factory, intersecting with the Woodstock and Thompson turnpike, in 1812, facilitating travel and trade with both those towns. A road was also cut through the woods over Park’s hill in 1818, and the previous road pitching down to Blindy’s mills discontinued. The financial affairs of the company were very flourishing. Yarn was sent out for weaving all over the country, even as far as Brimfield, Mass. A dividend of $36,000 was made in one of the years of war, and so well established was the company that it was able to continue work during the succeeding embarrassments. Mr. Wilkinson was a strict disciplinarian, and looked carefully after the morals of the community. At his especial request the Windham Association furnished ” religious instruction ” at stated intervals, holding meetings in the brick school house. A Pomfret Woolen Manufacturing Company was incorporated in 1817. and erected buildings upon the Mashamoquet, but it suffered severely from the great flood the following year, and other causes, and disbanded after a time with pecuniary loss to its associates. Bridges and dams at Pomfret Factory and Bundy’s mills were carried away by that almost destructive freshet, which inflicted great damage upon all the manufacturing corporations of the country. The Killingly & Pomfret turnpike was discontinued after a time and the bridge built for its accommodation removed. The great flood of 1817 compelled the erection of new bridges at Pomfret Factory.
Source: History of Windham County, Connecticut, Bayles, Richard M.; New York: W.W. Preston, 1889