School matters, like most all other public enterprises, suffered delay in the early years of this town, while it was part of Voluntown. In December, 1732, it was voted ” That there shall be a surkelating school kep and a school-master hired at ye town’s charge.” In March, 173.5, it was further ordered, ” That the school be kept in four places, three months in a place, six months in ye north end and six months in ye south end, dividing ye town by a line from Alexander Gordon’s to Ebenezer Dow’s house-and that the master, John Dunlap, should have thirty pounds money, and sufficient meat, drink, washing and lodging, for keeping school eleven months and eighteen days, and in ye night, when convenient.” The first school house in the town was built in 1737, ” four rods from ye northwest corner of ye meeting house,” and a rate of twopence allowed for the same.
In 1762, John Gordon was chosen grand school committee, ” to take into his hands the school bonds belonging to the town, and to collect the interest on bonds, and to receive the proportion of money granted by Government to the town out of the Colony’s rate, and to dispose of the same, and all other money coming from Plainfield, &c., and town’s proportion of the sale of Norfolk.” In 1766, David Eames, John Cole, Joseph Parke, Thomas Douglas, John Gaston, John Gordon and John Wylie, were appointed to set out school districts throughout the town. Thirteen districts were specified, each of which thenceforward managed its own school under the supervision of a “grand-schoolcommittee-man,” appointed by the town.
June 9th, 1794, John Douglas, Jr., was chosen grand school committee man, and a committee of one for each of the seven school districts, viz: 1. Jencks Mason; 2. Noah Cole; 3. Elisha Perkins; 4. Lemuel Dorrance; 5. Asa Whitford; 6. Nathan Dow; 7. Nathan Burlingame.
After the organization of the town of Sterling improvements in schools were gradually effected. Ten school districts, accommodated with good, convenient schools, were reported in a few years. Efforts were made to establish an academy, a company formed, and a suitable building erected, ” standing near our new meeting-house, nearly in the centre of the town,” where a “manschool was maintained throughout the year, teaching reading, writing, mathematics and grammar.” With these public buildings, Robert Dixon’s well-known tavern stand, and several large, substantial houses built by the Dorrances and other thrifty residents, Sterling hill presented a fine appearance, and received especial commendation from Doctor Dwight. After noting the lean soil and imperfect civilization of Western Rhode Island, he proceeds:
” At Sterling we were pleasantly advised that we had come to Connecticut by sight of a village with decent church and school-house and better houses. A beautiful prospect from Sterling Hill.”
Source: History of Windham County, Connecticut, Bayles, Richard M.; New York: W.W. Preston, 1889