The roughly 26 square miles that comprise Oakland were first settled by colonists of English descent who came from Massachusetts and New Hampshire in the latter half of the 1700s. At that time the area was known as Taconnet, which is derived from one of the four tribes of Native Americans who first occupied this region. The area was incorporated as Winslow in 1771. In 1872, the area west of the Kennebec effected a peaceful secession and incorporated as Waterville. In 1873, the manufacturers in the western section, who had created a separate center of activity and trade and were unhappy about taxation, incorporated as West Waterville. In 1883, the residents voted to rename their town Oakland.
Manufacturers long have been drawn to Oakland because of the water power provided by Messalonskee Stream. Oakland once was known as the ax and scythe producing capital of New England. With changing technology, newer industries such as the Cascade Woolen Mill replaced the agricultural equipment industry. In recent times, Oakland has witnessed another change in its industrial base. Older industries have closed, making way for new companies such as Valley Distributors, Industrial Metal Recycling, and Wrabacon, Inc.
Oakland lies within easy commuting distance to jobs and services in the Waterville and Augusta region. The completion of I-95 in the 1960s increased Oakland's relationship with the Augusta area, and to some extent the Greater Portland and Bangor areas. The Kennebec Regional Development Authority, a consortium of 24 towns in the Kennebes county area, is currently developing a high technology center next to Interstate 95 in Oakland with the help of state and federal funds. First Park is expected to become Maine's premier technology and business park.
(Bulk of text taken from the Oakland, Maine website)