The most pressing duty for our ancestors to perform, after securing a name and legalized status for the town, was the settlement of “an able, orthodox, godly minister.” The Rev. Josiah Dwight, a graduate of Harvard College in the class of 1687, received the appointment, and was installed October 17, 1690, receiving £40 the first year, £50 the second, and £60 the third year and thereafter. It was with difficulty, however, that these sums were paid, and when, some years after, the account was settled by the payment of what was due, he gave a receipt in full “from the beginning of the world to May 6, 1696.” A home lot was allowed Mr. Dwight according to the original drawing of lots, and arrangements were made to build a home for him immediately after his settlement. The following year,53 it was determined to construct a house of worship, which was completed early54 in 1694. This was the first meeting-house in Windham County, and here gathered, on Sabbath days, the settlers from miles around. The people of Pomfret attended church in this rude structure until 1715, when their own society was organized.

The officers of the new town elected in 169055 were John Chandler, Sr., William Bartholomew, Benjamin Sabin, John Leavens, and Joseph Bugbee, as selectmen, and John Chandler, Jr., as town clerk. All of those men to-day have descendants in Woodstock or its immediate vicinity. At that time, the men of Woodstock imposed a fine of one and six pence upon every one who failed to attend the town meeting, and six pence an hour for tardiness. Disputes regarding titles to land, and the boundary line dividing the north half of the town, and disputes with the mother-town regarding this northern half, which belonged to Roxbury according to the terms of the grant, were vexatious, and not in every respect creditable to Woodstock. But Roxbury’s interest in the northern half of Woodstock continued till 1797, when the lands had all been sold or become individual property. Large tracts, however, were held by Roxbury and Woodstock speculators for many years afterward.

Troubles with the Indians, who returned to their old hunting and fishing haunts after the settlement of the town, broke out in 1696,56 and again in 1700 and 1704, and even as late as 1724. When a war broke out abroad, there was trouble with the Indians at home. When an Indian outbreak was threatened, the town received some military assistance from the colony government. Such threatened outbreaks retarded the progress of the settlement.

After discussing the question for several years, the town determined, in 1719,57 to erect a new meeting-house near the burying-ground, instead of at the south end of the village, where the old building stood, yet so straitened were the people in their circumstances that they applied to the General Court in Boston, requesting that the unoccupied lands of the residents and non-residents of the town be taxed to the extent of £250, to be applied to the building of a church. As the non-residents’ lands were almost entirely in the north half of the grant, and belonged to Roxbury people, Roxbury stoutly opposed the tax in a memorial to the General Court. When the General Court refused the petition, Woodstock asked to be excused from sending her representative to Boston. The town’s representative at this time, in fact the first and only representative for many years, was Captain John Chandler, who, like his father Deacon John Chandler, was one of the first settlers. He surveyed lands in Woodstock and neighboring towns, and owned large tracts of territory in Connecticut and Massachusetts. To avoid the necessity of sending to Boston to have deeds recorded and wills proven, Captain Chandler tried to get the consent of the General Court in 1720 for the formation of a new county, to be called Worcester County, of which Woodstock should be a part, but a delay ensued until 1731, when Captain, now Colonel, Chandler was successful. Woodstock became one of the most prominent towns of Worcester County, and John Chandler was made Chief-Justice of the Court of Common Pleas and General Sessions.58