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From The Town of Woodstock:
In 1636, Thomas Hooker and his party may have passed by way of the Connecticut Path, going to settle what is now Hartford.
In 1674, John Eliot, Apostle to the Indians, Pastor of the First Church in Roxbury, Massachusetts Bay Colony, and Daniel Gookin' visited a peaceful encampment of Wabbaquassets living in the vicinity of present-day Woodstock to preach from nearby Eliot Rock and sought to establish their church among the natives of these lands. King Philip’s War broke out in 1675, during which the Wabbaquassets deserted the area.
The site was chosen as a place of settlement, and on April 5, 1686, from Roxbury came Peter Aspinwall, Thomas Bacon, Henry Bowen, Matthew Davis, John Frizzel, John Gore, Nathaniel Gray, Benjamin Griggs, George Griggs, John Marcy, Ebenezer Morris, Benjamin Sabin and Jonathan Smithers. These men were known as the Thirteen Goers who founded the Town of New Roxbury, the first European settlement in the area that became Windham County.
Seventeen lots were then assigned in the eastward vale, viz.:
Lots 27, Samuel Scarborough, and 28, Samuel Craft, were laid out on the east side of Plaine hill.
The home lots on the westward hill were made over to eight persons, viz.:
Lot 37, Edward Morris, thirty acres, was laid out east side of Plaine hill, ” bounded west by the great highway; south partly by land reserved for public use and partly by land of Samuel Craft and Samuel Scarborough; east by common land; north upon the highway that goeth from the street to the Great Pond.”
It was agreed by vote that the number of shares should be limited to fifty. The remaining allotments were distributed within six years to the following settlers:
These fifty proprietors were all previous residents of Roxbury, with the exception of Peter Aspinwall, of Dorchester; John Holmes, Dorchester; the three Corbins from Muddy river (Brookline); the Bartholomews, from Branford; John Butcher, Boston; Philip Eastman, Haverhill. Many were united by family ties, as fathers, sons and brothers.
Of the older men, Henry Bowen, Samuel Craft, William Lyon, Sr., Samuel May, Samuel Scarborough, returned to their Roxbury homes, leaving their New Roxbury land with sons or purchasers.
Jonathan Smithers, John Bowen, William Lyon. Jr., John Ruggles, failed to retain possession.
About forty of the original proprietors remained in possession of their home lots thus assigned to them – the fathers and founders of the town of Woodstock. All subsequent divisions of land in the south half of the grant were based upon the number of acres in each man’s home lot, and public charges were laid in the same proportion. Part of the ” Go-ers ” had brought their wives and children, and hastened to put up houses and establish household life.
November 3d, 1686, a proprietors’ meeting was held at the house of Thomas Lyon. John Chandler, Sr., Joseph Bugbee – and Edward Morris were chosen a committee for the oversight and ordering of public affairs. A committee was also chosen ” to treat with young Mr. John Wilson of Medfield to come and preach to the planters in order to settlement.” Religious services were held in the open air this first autumn, a large rock by the roadside on the way to the westward hill serving for a pulpit; but settlement was not sufficiently advanced for a stated minister.
This section from " History of Windham County, Connecticut", Bayles, Richard M.; New York: W.W. Preston, 1889 (see resources below)
Given the name “Woodstock” by Judge Samuel Sewall in 1690 “…because of its nearness to Oxford, for the sake of Queen Elizabeth…” the Town remained a part of the Massachusetts Bay Colony until 1749, when it seceded in favor of becoming a part of the Connecticut Colony.
From the hills of Woodstock went Captain, later General, Samuel McClellan following the alarms sounded from Lexington and Concord in 1775, together with 184 men, who responded in a greater number than from any other town in the Colony.