In the 1660s early settler John Kettell likely lived "in the vicinity of Pompassiticutt Hill, on land now included in Maynard" before the warfare of King Philip's War caused him to flee at the time of the Lancaster raid.

[2] In 1676 during King Philip's War, Native Americans purportedly gathered on Pompasitticut Hill "near the spot where the remains of the foundation are" to plan their attack on Sudbury.

Blood cut off his woodlot on Pomciticut Hill winter before last" which "deforms a hillside" but "all the villagers obtain compensation in the crop of berries that it yields.

"[9] In 1871 Maynard became an independent town, and hosted a celebration where several citizens "raise[d] a flag staff on Pompsiticut hill.

"[10] By at least 1891 the north and west sides of the hill contained "excellent orchard and plow-lands"and the south side contained "a fertile valley and many broad acres of fine pasturage," and on the summit there was at that time a reservoir (built in 1888)[11] and an unobstructed view to Mount Wachusett and Mount Monadnock in New Hampshire.