The area that is now Oakland was first settled in about 1780 by colonists of English descent from Massachusetts and New Hampshire.

Farmers found the area's fertile soil good for cultivation, grazing and dairy farming, while the water power provided by the Messalonskee Stream was useful for manufacturers.

The area was incorporated by the Massachusetts General Court in 1771 as part of Winslow.

In 1802, the area of Winslow west of the Kennebec River was incorporated as Waterville.

The Androscoggin and Kennebec Railroad arrived in 1849, spurring Waterville to boom as a mill town.

With several manufacturers of farm implements, it became known as the axe and scythe capital of New England.

Other factories produced canned goods, tinware, carriages, furniture, tools, machinery, woolens, lumber, coffins, leather, boots and shoes.

In 1872, Oakland became the southern terminal of the Somerset Railroad, connecting first to North Anson, then to Bingham, and finally to Moosehead Lake.

[4] The town's ponds and lakes are home to a number of summer camps.

It borders the towns of Belgrade to the southwest, Smithfield to the northwest, Fairfield to the north, Waterville to the southeast, and Sidney to the south.

There is Messalonskee High School, which enrolls around 700 students, and has an 826-seat J. Duke Albanneese Performing Arts Center.