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Following the “Great Trail” through Upton

Map of the Great Trail/Old Connecticut Path from The Great Trail of New England by Harral Ayres. The Great Trail is illustrated as a dashed double line.

Did you know that the legendary "Great Trail" of the Native Americans, which in colonial times became the settlers' Connecticut Path, passes through Upton? The trail followed the most passable, direct, foot route from Boston and Cambridge, through the heart of Nipmuc lands in central Massachusetts and northeast Connecticut, to rich fishing grounds on the Connecticut River in Windsor. The trail served as a major thoroughfare along which people and goods moved-often seasonally-and near which native people gathered at common meeting places.

At the time of European contact, Upton like much of the area through which the Great Trail passed was open due to regular seasonal burnings. This made foot travel quite easy. Harral Ayres, author of "The Great Trail of New England" writes that it was: "a trail of importance to the Indians back through the ages. It lay on a surprisingly direct course between the long rapids of the Connecticut River above Windsor, and the salt-water beaches and havens of the Boston Bay. Well-distributed along its course were lakes, fishing places, hunting grounds, and other areas of interest in Indian life; and Indian towns and sachemdoms. The fordways of the rivers were easy crossings in normal weather; not one was hazardous

The Great Trail had two trailheads-one in Cambridge, and the other in Boston. The Cambridge leg traverses Watertown, Waltham, Weston, Wayland, and Framingham, where it meets up with the Boston leg. The Boston leg of the trail passes through Newton, Wellesley and Natick before merging with the Cambridge leg in Framingham.

From Framingham the Great Trail passes through Ashland, and then Hopkinton where it forks. Both the eastern and western forks pass through Upton on their way south.

The eastern fork enters Upton from the Upton State Forest as today's Old Elm Way. From there it follows Forest St. and then Elm St., passing within a stone's throw of the Upton Chamber. It then crosses 140, follows Brook St., and then the railroad tracks to the site of Upton's first cemetery and first meetinghouse. This location is at the intersection of another known Indian trail. From there, the Great Trail likely followed the course of South St. According to Ayres, the eastern fork crosses the Blackstone River at Riverdale.

The western fork of the Great Trail passes through the northwest corner of Upton where Westborough, Upton, and Grafton meet on Faye Mountain--just south of the Massachusetts Turnpike. In Grafton it passes through the "Praying Indian" village land of Hassanamesit. According to Ayres, the western fork fords the Blackstone at Farnumsville.

On Ayres' map, the two forks merge at Lake Manchaug in Sutton, and then through Oxford, Douglas, Webster, and Dudley to Woodstock, Conn.

After European contact, eight of the 14 "Praying Indian" villages, whose locations were chosen by native people, were along, or an easy walk from the trail. The villages served by the trail included Natick, Magunkaquog (now referred to as Magunco at Magunco Hill in Ashland), Hassanamesit in Grafton, Manchaug now Sutton, Chaubunagungamaug now Webster, Maanexit now Uxbridge, Quinnatisset now Thompson Hill, Conn., and Wabaquasset now Woodstock, Conn.

In his book, published in 1940, Ayres mentions Upton's stone chamber, "At Upton, on this Great Trail, is a large prehistoric stone cave or hut, built of huge untooled stones. It has withstood the ravages of an age. Nothing in American or Indian handiwork explains it. . . . Often in these studies something has cropped out to suggest that this old trail was as ancient as the countless centuries of Indian life itself; that it was the great trail of the aborigines through the ages! This cave house may someday reveal a strange story."

In Webster, as in Upton, the trail passes near an impressive stone chamber, and there are five chambers a short distance from the trail in Thompson, Connecticut. That these impressive structures are near the Great Trail may indicate its importance in native American life.


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