That post office was moved to the hamlet of Havana on April 18, 1860, which was two miles southeast of Oakleys present location.

In 1868, Andrew Huggins plotted and recorded the village of Oakley and the post office was moved from Havana.

It was named for Judge Oakley of Dutchess County, New York, a relative of one of its citizens.

Starting in 2009, the police department began to award donors with credentials as reserve policemen.

The reserve policemen had badges and identifications that exempted them from pistol-free zones while carrying concealed.

Some seem to have also retained bulletproof vests and other equipment bought by the village with their donations.

[8] The village disbanded its police department in September 2014 after the Michigan Township Participating Plan cancelled liability insurance for the department over concerns of its use of untrained police officers.

[9] [10] In October, a village official secured insurance from other sources and briefly tried to reestablish the department.

Issues related to the police department became important politically in the run-up to the November 2014 elections.

[11] In late November, the new town council voted to reinstate the police department.