First settled by the Minsi Indians of the Lenni Lenape Tribe and later Arent Schuyler representing his Dutch associates purchased from them the 5500 acres calling it "De Panne" or "The Ponds". By 1710, there were just 10 families calling the area home. Throughout the eighteenth century, the area developed as a farming and lumber community and by 1777 there were 100 families in the area. Roads were built replacing dirt paths during this time as it was a connecting line to West Point which at the time was an important place where couriers sent messages on planned campaigns. The railroad arrived in 1869 and clearly made the area more accessible. It swiftly became known as a tourist vacation spot for hunting and fishing. In 1870 the name of the town was changed to Oakland and by 1902 was incorporated as the borough of Oakland. After WWII, Oakland began rapid development and by 1950 earned the title of "Valley of Homes" in local magazines.

Today, Oakland has a population of 12,500 residents and covers 8.6 square miles. It has modest sized  homes  to larger homes mostly built from the 1950 to the present. There is not much shopping in Oakland but is a short ride to the Paramus and Wayne malls. There are local assorted convenience stores along the main thoroughfare of Ramapo Valley Road.

There is no commuter rail service in Oakland however there is a commuter busline  that runs to Port Authority in NYC. Route 208 was completed in 1962 and with the completion of Rt 287, Oakland became very accessible to all major areas.

Oakland supports three neighborhood k-5 elementary schools, Dogwood Hill School, Heights School and Manito School, Valley Middle school grades 6- and Ramapo/ Indian Hills Regional High Schools grades 9-12. Oakland is very proud of their public library, their senior center,  many recreational programs including 6 tennis courts and a roller hockey rink. Ramapo Mountain State forest is located in Oakland and provides many hiking trails to enjoy.