This fertile wilderness valley of the Sandy River was originally known as Shadagee, derived from the Indian name Chatauke, meaning "Great Place". The first settler to come was Perkins Allen, a sea captain from Martha's Vineyard, who in 1790 settled on the property now known as Whip-Poor-Will Farm. This farm was sold to Seth Greely, who built the first frame house on it and held the first church service and school in his barn.

Soon after 1790 several other families journeyed into this wilderness, coming from southern Massachusetts and New Hampshire towns. These first names recorded in old records included Greeleys, Churches, Davenports, Whitneys, Tufts, Howards, Thompsons, Hoyts, Pratts, Wilburs and others. By 1805 there were 21 families in a widely scattered area on both sides of the Sandy River.

Farming was the principle occupation of the first inhabitants of this region, and the life was extremely hard. Clearing the primeval woods, erecting cabins for shelter, and persuading the land to yield enough annually to sustain the family through the winter was indeed rugged work. The most successful settlers were those who brought plenty of help along, such as Micah Whitney, who arrived in Phillips in 1810 with a family of twelve.

Clearing the land for farming could yield a valuable source of income from farmers who gathered the ashes of their burned woods. They would leach the ashes and boil down the leach to create a liquid called pot-ash. This pot-ash could be further boiled down to create pearl-ash which was worth even more. Biscuits made with pearl-ash as leavening were said to be tops.

Settlers raised wheat and other small grains. So successful was this early grain production that Western Maine began to be called the bread-bowl of the nation.