To appreciate the importance of Skowhegan in Maine’s history, it is necessary to consider the location of the island of that name in the Kennebec River Valley. Situated halfway between the river’s Moosehead Lake headwaters and the head of tide below Augusta, Skowhegan Island’s unique geology and central location made it both a place to visit and served as an east/west crossroads for Native Americans, and so it remains today.

For thousands of years before the first white man arrived at Skowhegan Island, the area was used by Maine Native Americans. They speared salmon and other fish in the pools beneath two waterfalls there and utilized the rich land on its banks to raise corn and other crops. This place was an important stop on their annual migrations from northern hunting grounds in winter to coastal Maine in summer. They dried fish on the Island in early summer and planted crops to be harvested on their return northward in autumn.

There is uncertainty of the origin and meaning of the name Skowhegan. One source says that in the Abnaki language it means "Falls by the Pine Plain Lands.” Another says that "Skowhegan" is the Native American word for "spearing" or "place to watch." Most historians lean toward the latter translation but either would have been descriptive. Just north of Skowhegan Island are several square miles of level ground sitting atop an aquifer of clear fresh water. The soil is sandy but fertile and typically would have been covered with scattered pine trees. This was a perfect place for the Native Americans to camp and grow crops, surrounded by miles of dense forests. In any event, the name Skowhegan was used by the Native Americans long before the first white settlers arrived to build their own community and adopting the same name.

The Kennebec Valley in the District of Maine was a rich source of furs and fish, timber and cropland unlike the first successful English settlement in New England, the Pilgrim Colony at Plymouth, Massachusetts, established in late 1620. Those first settlers faced a terrible struggle for survival, losing half their number to disease and starvation in the first winter. The Plymouth area was not well endowed with the raw materials needed by the Pilgrims to feed themselves and repay their debts to the settlement’s financial backers in England. In 1629 the Council for New England granted to a group of Pilgrim leaders at Plymouth a tract of land on both sides of the Kennebec River. This tract actually extended from Woolwich to Cornville and included the entire present area of Skowhegan. After 1691 this property, including what is now Skowhegan, would become a part of the Province of Massachusetts Bay. Setting up trading posts at convenient locations to meet and trade with the Native Americans gave the Pilgrims the opportunity to financially secure their settlement and later to provide the basis for property sales under the management of the descendents of those original owners, now known as the Kennebec Proprietors. After the Kennebec Valley became safe for settlers at the end of the French and Indian wars in the 1760’s, the Proprietors began to survey, sell and settle their newly created lots.

The first white settlers arrive: