A glimpse into the earliest days of the Town of Gray is recorded in A History and Description of New England, General and Local by Austin Jacobs Coolidge and John Brainard Mansfield:
Gray is situated in the central part of Cumberland county, and was originally owned by inhabitants of Boston, to whom it was granted December 3, 1735, upon petition of the general court of Massachusetts, representing that they had large families and were in straitened circumstances. Several years intervened before a settlement of the township could be effected; but in the mean time there were frequent meetings of the proprietors in Boston, generally held at the Sun Tavern, and sometimes at the British Coffee-house. One of the first settlers – probably the first – was Moses Twitchell who came from Westboro, Mass. Jabez Matthews and William Webster followed soon after; and in the course of fifteen or twenty hears, several other families moved in. In 1756, the proprietors made a report of the progress of the settlement to the legislature, in which they state that they had laid out sixty-three lots of sixty acres each for settling lots, had built a meeting-house, erected thirty-six dwelling-houses, and cleared a part of the lands as required by the conditions of the grant; but that they had been put to great expense and suffering.
The settlers were in constant fear of hostile Indians, who at one time came upon the settlement in great numbers, destroyed the cattle, burnt the meeting-house and all the dwelling-houses, and obliged the settlers to flee to places of safety. After peace was concluded with the Indians, some of the inhabitants returned and erected a new meeting-house, as well as a block-house, fifty feet long and twenty-five feet wide, around which they erected a garrison, one hundred feet long and seventy-five feet wide, which was supplied with military stores. Soon after, a rumor of war with France terrified the settlers and they fled the second time; but the fort was not altogether forsaken, and, gradually, families obtained sufficient confidence to venture to take up a permanent abode here. At first the township was without a name, being known only as a proprietory lying on the back of North Yarmouth, in the county of York. About the year 1756, it bean to be called New Boston. In 1778, by act of legislature, it was incorporated and called Gray, as it is supposed, in honor of Thomas Gray, one of the proprietors.