It should now be related how Woodstock, settled under Massachusetts, became a part of the State of Connecticut. Massachusetts claimed Woodstock, because the grant was supposed to lie within her chartered bounds as surveyed in 1642, and that claim was what Major Daniel Gookin referred to when he rebuked the agent of Uncas in 1674, during his visit with John Eliot, at Woodstock. But Massachusetts did not believe that the line of 1642 was wrong when she confirmed the grant to the Roxbury settlers. She even censured Woodstock for daring to ask Connecticut to confirm a portion of the grant that fell south of this line. Though Connecticut justly held she was entitled to Woodstock, according to the terms of her charter, she was, nevertheless, willing to forego her claim to this town, provided Massachusetts would allow her to have the jurisdiction over other territory claimed by both colonies. But the repeated attempts to settle the controversy failed, and it was not till 1713 that an agreement was finally concluded. For the privilege of having jurisdiction over Woodstock and the other towns claimed by both sides, Massachusetts agreed to compensate Connecticut, by giving her unimproved lands in Western Massachusetts and New Hampshire. These lands were therefore called “equivalent lands,” and were sold by Connecticut for $2,274, and the money given to Yale College. Woodstock was entirely satisfied with this agreement, as all her associations were with Massachusetts. But in 1747 the town thought that her taxes, which had been increased owing to the French and Spanish wars,83 would be lighter, and her privileges greater, if she followed Suffield, Enfield, and Somers “in trying to get off to Connecticut.” So Woodstock applied to Connecticut, claiming that the agreement of 1713 had been made without her consent. After much deliberation, Connecticut voted in 1749 to receive the town, and declared the agreement of 1713 not binding. Woodstock was delighted at being received into Connecticut, and at a memorable town meeting84 made Thomas Chandler and Henry Bowen the first members of the General Assembly. Though Woodstock has since 1749 been a part of this State, Massachusetts would never formally yield jurisdiction over the town, and even as late as 1768 warned the inhabitants not to pay taxes to Connecticut. In fact had it not been for the Revolution, Massachusetts might still be claiming Woodstock.85 It might be added that Woodstock, in being annexed to Connecticut, lost about three thousand acres north of the colony line. This strip of land was known as the “Middlesex Gore” for forty-five years, and was annexed to Dudley and Sturbridge in 1794.

After becoming a part of Connecticut, Woodstock was anxious that the northern half of Windham County should be made into a separate county, of which Woodstock should be the shire-town, but as Pomfret also desired the county seat, and as the State seemed unwilling to act, the project fell through.86