Oakland was incorporated as a borough by an act of the New Jersey Legislature on April 8, 1902, from portions of Franklin Township (now Wyckoff). The name comes from the white oak trees in the area. The Van Allen House was built in 1748 and was a stop for George Washington and his troops in 1777.

From the 1940s through the end of the 1960s a summer bungalow colony was developed in a valley in West Oakland on the Ramapo River. This was a refuge for a close-knit group of several score families from the summer heat of New York City and urban New Jersey. During the summer months, the New York, Susquehanna and Western Railroad provided service at a West Oakland passenger station. This colony was located on the road between Oakland and Pompton Lakes, near a training camp for boxers. In the early morning, a resident could see Joe Louis or Sugar Ray Robinson, among others, running past the summer homes.[citation needed]

One section of streets in the town are named after Native American tribes and Native American first names. Now considered politically incorrect, the borough had a wooden sign posted downtown that read "Once there was [sic] Indians all over this place" which had been donated by a resident who insisted on the wording of the sign as having been a quotation from an author.

Education​
Public school students in kindergarten through eighth grade attend the Oakland Public Schools. As of the 2018–19 school year, the district, comprised of four schools, had an enrollment of 1,362 students and 132.2 classroom teachers (on an FTE basis), for a student–teacher ratio of 10.3:1. Schools in the district (with 2018–19 enrollment data from the National Center for Education Statistics) are Dogwood Hill Elementary School[112] with 247 students in grades K-5, Heights Elementary School with 347 students in grades K-5, Manito Elementary School with 266 students in grades K-5 and Valley Middle School with 473 students in grades 6-8).

Students in ninth through twelfth grades for public school attend the schools of the Ramapo Indian Hills Regional High School District, a regional district serving students from Franklin Lakes, Oakland and Wyckoff. Students entering the district as freshmen have the option to attend either of the district's high schools, subject to a choice made during eighth grade. Schools in the district (with 2018–19 enrollment data from the National Center for Education Statistics) are Indian Hills High School, located in Oakland (1,062 students) and Ramapo High School, located in Franklin Lakes (1,222 students). The district's nine-member board of education oversees the operation of the district; seats on the board are allocated based on population, with three of the nine seats allocated to Oakland. Franklin Lakes, Oakland and Wyckoff (FLOW district) approved the creation of a regional high school in 1954 by a vote of 1,060 to 51, with Ramapo High School (in Franklin Lakes) opened in 1957 and Indian Hills High School in 1960.[citation needed]

Public school students from the borough, and all of Bergen County, are eligible to attend the secondary education programs offered by the Bergen County Technical Schools, which include the Bergen County Academies in Hackensack, and the Bergen Tech campus in Teterboro or Paramus. The district offers programs on a shared-time or full-time basis, with admission based on a selective application process and tuition covered by the student's home school district.

Private schools include Barnstable Academy, a college preparatory school for students in fifth through twelfth grades located in a business and industrial park off Long Hill Road; The New Jersey Japanese School, which serves Japanese expatriates to prepare them for the Japanese educational system when the students eventually return to Japan, located next to Our Lady of Perpetual Help Church; and the Gerrard Berman Day School (Solomon Schechter of North Jersey), a Jewish day school for students in preschool through eighth grade, located on Spruce Street

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