For at least 2,000 years, Nipmuc towns along the Towanucksett and Quinneticut Rivers called the area covering what are now South Shutesbury, NE Amherst and parts of Pelham "Sanakkamak", meaning "difficult land", according to the Indian Land Archives of Springfield (1660–1835), now housed at Cornell University. According to the same archives (pages 31–33), the land was named Sanakkamak "on accord of its many ponds, swamps, and streams" leading to steep slopes of Kunckquatchu (Mt. Toby) and Quaquatchu (Brushy Hill). The northern parts of Shutesbury, as well as parts of Belchertown and Pelham along the former Swift River (now Quabbin Reservoir), were called "Kingyiwngwalak", meaning "Upturned land" due to the heavily titled bedrock of the area and many steep ravines draining to the east and south (Indian Land Archives of Springfield, Cornell Univ.).

Indian Land Deed Archives record that the land was used for hunting, fishing and collecting wild staples, such as chestnuts, hopniss (Indian potato, Apios americana), blackberries, blueberries, service berries, sunflower root, and for cutting timber. Sachems holding rights to the land in Shutesbury specifically inserted a clause in the deeds that "they, their descendants and assigns retain the right to hunt, fish and take wood from the lands they have thus deeded, and the English shall not prohibit them from taking wood and fish, and shall be friendly and neighborly toward them" (edited for modern spelling).

Shutesbury was colonized in 1735, when it was called Road Town, because the original request by Colonists to Boston was to build a road in a roadless area. Road Town was officially incorporated as Shutesbury in 1761. The town was renamed in honor of Samuel Shute, former governor. Town building requirements initially required each Colonist family to clear four acres of forest and plant grazing grasses. After the Revolution, the entire area and most of Massachusetts were clear-cut and sheep grazing predominated during the brief textiles boom, which was overshadowed by wool production in the West, Australia, and New Zealand (Massachusetts Historical Preservation Commission publication online). Only after the Civil War period was the area largely reforested. Croplands have shrunk steadily in the period since then, being the most at-risk land category in the Town Master Plan. Post-1960, croplands in Shutesbury saw sharp reduction, while residential has remained the fastest-growing land use type since. Forest cover is the second largest sector of land use loss since 1960 and remains so, after croplands. Population has risen since 1960, with several short periods of population loss.

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