The original township of Killingly was laid out north of Plainfield in 1708. It occupied the northeastern corner of Connecticut, in the wild border land between the Quinebaug and Rhode Island. This region, called the Whetstone country, was known to the white settlers of the surrounding towns, but was for a long time neglected. It was owned by the colony of Connecticut and not by individuals or companies, and tracts of it were given by the government in recognition of civil or military services rendered it. Its first white proprietors were thus the leading men of the colony. Governors Haynes, Treat and Saltonstall; Majors Fitch and Mansfield; the Reverend Messrs. Hooker, Pierpont, Whiting, Buckingham, Andrews, Noyes, Woodbridge and Russel; the Hons. Giles Hamlin, Matthew Allen and Caleb Stanley, had grants of land here and were associated with the early history of Killingly. The grant to Governor Haynes was given as early as 1642, that to the Reverend John Whiting in 1662, but the greater number at a later period. These grants were not located, but simply conveyed a specified quantity of land to be selected by the grantee according to his pleasure, so long as it did not ” prejudice any particular township or former grant.”
The first to take possession of land in the Whetstone country under these grants were Major James Fitch and Captain John Chandler. A grant of ” fifteen hundred acres, to be taken up together and lyeing beyond New Roxbury, near the northeast corner of the Colony line,” was confirmed to Major Fitch by the general court, in October, 1690. With his usual dispatch and discrimination, Fitch at once selected and had laid out to him the best land in the whole section-the interval between the Quinebaug and the Assawaga, extending from their junction at Acquiunk to Lake Mashapaug, and also the valley east of the Assawaga, as far north as Whetstone brook. Captain John Chandler of Woodstock, was next in the field, buying up land granted to soldiers for services in the Narragansett war. Two hundred acres purchased by him from Lieutenant Hollister were laid out at Nashaway, the point of land between the Quinebaug and French rivers, and confirmed to him by the general court in 1691. A great part of the valley land adjoining French river, and a commanding eminence two miles east of the Quinebaug, then known as Rattlesnake hill, afterward Killingly hill, were speedily appropriated by Captain Chandler. The other grantees, less familiar with the country, and less experienced in land grabbing, found more difficulty in taking up their grants. The country was not easy to explore. Lack of roads, swelling streams, deep marshes, tangled forests and refractory Indians, all conspired to make the task of locating land claims at that time particularly laborious and hazardous. The Reverend Samuel Andrews succeeded in having his grant of two hundred acres laid out in 1692, west of Rattlesnake hill, bounded on three sides by wilderness.