According to Hannah Swart in her book Koshkonong Country – A History of Jefferson County, Wisconsin, four families were known to have settled in Oakland in the 1830’s . Among the early pioneers of Oakland were Mr. and Mrs. Erastus G. Snell, originally from Connecticut, who settled on Red Cedar Lake. Red Cedar Lake House was established by the Snell’s for stagecoaches using an old Indian trail from Milwaukee to Madison now known as USH 12. Eliza Marie Snell was the first Caucasian child born in Oakland on October 12, 1840.
Gideon and Holmes Ives came to Wisconsin in the spring of 1843, purchase 224 acres of land in the area, and named the township of Oakland.
After the death of his first wife, Mr. William Eustis left Oakland with his children, remarried, and returned with his new family in 1846. After building the only stone octagon house of its kind in town, the voters elected Eustis to the State Legislature. He was also Town Assessor, Clerk and Supervisor.
The Crane brothers, originally from Vermont, established the first post office in 1846 around the time Moses Powers brought his family from New York. Moses was a restless man, always looking for gold before settling down to farm, served as Postmaster and Town Assessor.
The Goodrich’s son, Perry, was judged at state fairs on his butter of excellent quality and was elected Justice of the Peace and County Surveyor.
Robert Robertson came from Scotland in 1857 and entered into a partnership as the cheesemaker for the Oakland Cheese Factory. In 1873 he married Ellen Silverthorn, daughter of the town’s first school teacher Sarah, whose family migrated from Canada.
Lake Ripley was the home of Ole Evenrude who, in 1908, invented the outboard motor and founded a new American industry.
To the present day, Oakland Township has retained its agricultural characteristics while also attracting tourists with Lake Ripley and Red Cedar Lake.To date the population of Oakland Township is 3,088.