The first settlers of the region around Skowhegan were a small group of pioneers from southern Massachusetts who arrived on an island two miles south of the Great Eddy of the Kennebec in the spring of 1771. At this time, the province of Maine was part of the Massachusetts Bay colony. To avoid geographical confusion it should be mentioned that although the Province of Maine had been placed under the governance of the Massachusetts Bay Colony in 1691, the two properties, then as now, were separated from one another by New Hampshire. Thus, the Kennebec Valley was several hundred miles north of the area of Massachusetts from which most of the early settlers came. There were no convenient roads between the two areas and those first pioneers in 1771 came by ship up the Kennebec River to the head of tide near Gardiner. From there, they made their way upriver on the eastern side to Winslow, in the area of Fort Halifax. There, any semblance of roads ended and it was necessary to follow rough Indian trails on the eastern bank of the river about twenty-five miles to their destination. Because they were driving livestock it was sometimes necessary to clear these paths of fallen trees. The two men in the first party cleverly made saddle bags strapped to the backs of their cattle that carried most of their equipment and supplies.

Their first place of settlement was an island in the River of about nine acres in size that was part of the property belonging to Joseph Weston. This was perfect for their needs as it had been kept cleared earlier by Indians and required little preparation for planting crops. Also, the island, being surrounded by water, there was no need to build fences for the livestock. How the party managed to get their animals from the east bank of the river to the island was never mentioned in their records.

The group consisted of Peter Heywood of Concord, his son Asa and Isaac Smith, who lived with the Heywoods. The party included Heywood’s brother-in-law, Joseph Weston of Lancaster and his son Eli. They built a cabin, planted corn and potatoes and cut hay for their cattle. In late summer Heywood, his son Asa and Joseph Weston returned to their hometowns, leaving two of the boys, Eli Weston and Isaac Smith, to finish harvesting their crops and tend the livestock. Unexpected delays caused both families to wait until the following spring to return, leaving the two boys to spend the winter alone on the island. Weston and Heywood brought the rest of their families back to the small settlement in April of 1772. The two boys, aged twelve and seventeen, had survived the winter successfully, and the livestock were in good health. For the next three years these first settlers and a small number of newcomers labored to develop their farms and build a community.

Looking back to the early days it seems strange that those first settlers would voluntarily subject themselves to the hardships of pioneer life. Those first two families, the Westons and Heywards, were led by people in their middle years, already successful in their businesses before rearranging their lives and moving to the wilderness. Why would they do that? The answer can be expressed in one word: Land. Not just any land; affordable, beautiful property comparable to any in North America. Heavily timbered land that could be cleared for farming, and had abundant waterpower to power mills; land filled with fish, game and fur-bearing animals.

By arrangement with the Kennebec Proprietors, Joseph Weston and two of his sons, Joseph Jr. and Samuel, Peter Heyward and his son Peter Jr., each acquired two hundred acres in five adjacent lots on the western side of the river totaling one thousand acres, several miles downstream from Skowhegan Island. What was the cost? Commonly, each landowner agreed to build a home and farm buildings, clear at least ten acres of cropland in a ten year period and the land would be theirs permanently thereafter. The motivation of the Kennebec Proprietors seems to have been an effort to entice reputable settlers to form the nucleus of a successful community, thereby making their many unsold lots more attractive.

How did these two families come to be chosen to be the first recipients of this incredible offer from the Kennebec Proprietors? No records seem to exist but a clue can be found in papers relating to the survey. “The valley of the Kennebec was surveyed by John McKechnie and John Jones, who drew a plan, dated November 7, 1769.”

John Jones, who undoubtedly knew the best portions of the surveyed property and the plans of the proprietors, was related by marriage to both Peter Heyward and Joseph Weston. Peter Hayward became a land agent for the Kennebec Proprietors and oversaw the selling of many of the surveyed lots in Canaan.

Joseph Weston died in October of 1775 as a result of the hardship and exposure he had undergone assisting the Arnold Expedition. His wife, Eunice Farnsworth Weston, left alone with nine children, married Major John Moor in 1779. Moor owned large tracts of land along the Kennebec and generously shared his property with his wife's children. The Weston sons contributed to the growth of the area and many of Skowhegan's later residents descended from them. The Westons were a prolific family and thousands of people can now trace their ancestry back to Joseph and Eunice. When Eunice died in 1832, she left behind 222 living descendents. Eunice and her first husband, Joseph, were buried in the oldest graveyard in town, the Bloomfield Weston cemetery, very near to where they built their first cabin. Their graves may be seen there today. The cemetery is located on route 201 south, about three miles from town.

Other early settlers from southern Massachusetts were Jonathan Oaks, who came in 1772 from Marlboro, Eleazer Coburn who came that year from Tyngsboro, John White, who arrived in 1773 from Lancaster, and Seth Wyman who came from Townsend in 1773. For several years, the community, now called Canaan, slowly increased in population and established the first elements of local government and essential services.

The Revolutionary War and the Benedict Arnold Expedition