Earliest of the public schools in the Oakland Area was the Cheltenham School erected in 1868. At that time it was in St. Louis County and was located near what is now Graham Street and West Park Avenue. Typical of the rural schools of its time, it was a one-story frame building of two rooms, with seats for 110 pupils. By 1875, it was known as District School No. 3. As the area west of Cheltenham was built up, a school was opened in 1870 on Manchester Road near the Benton station on the railroad. It was similar in appearance to the Cheltenham school building, although its two rooms could accommodate 90 students.

In 1882, after its district became a part of the city school system, the Cheltenham School was replaced by the Charles Gratiot School at what is now 1615 Hampton Avenue. This was a two-story brick structure, which was enlarged by two wings in 1899 and 1919. Gratiot, 1752-1817, was the first presiding judge of the town of St. Louis and the owner of the Gratiot League Square.

With the development of subdivisions near the Hi-Pointe area, the need for a public school was met by the completion of the George Dewey School at 6746 Clayton Avenue in 1917. It was named for the Spanish-American War admiral and was one of the first St. Louis school buildings designed by architect R. M. Milligan.

Two other schools in the Oakland area were also designed by Milligan; these were the John J. Roe and Melville Wilkinson Schools. Roe School, at 1921 Prather Avenue, was named for a wellknown St. Louis steamboat captain and was finished in 1922, with an addition in 1927. The Wilkinson School at 7212 Arsenal Street was opened in 1927, as the namesake of a St. Louis merchant.

The only secondary public school in the area is the John O'Fallon Technical High School at 5101 Northrup Avenue. It was opened in 1955 as a successor to the Hadley Technical School, from plans by architect F. Ray Leimkuehler. An annex was added to the school in 1970. O'Fallon, who lived from 1791 to 1885, was a prominent St. Louis philanthropist"

On the site of old Forest Park Highlands at 5600 Oakland Avenue, is the Forest Park Community Junior College, which was completed in 1966. Two years later additional class rooms, a cafeteria and a gymnasium were added to the college.

To the west of the Junior College, near where the Arena stands today, was the campus of the Forest Park University from 1891 to 1927. It was begun in 1861 as the Kirkwood Seminary by Anna Sneed Cairns and was the first university in the United States to be chartered solely for women.

Down the street, at 4970 Oakland, is the St. Louis University High School, a Roman Catholic institution that was completed in 1924. This school can trace its history, as the high school department of St. Louis University, back to 1818 when the University was founded as the St. Louis Academy. It remained as an integral part of the University and held classes in the University buildings on Grand Avenue, until its move to the present building in 1924.

By that time, several other high schools and academies had been combined with the St. Louis University High School. The high school's new building was a gift from Mrs. Anna F. Backer, as a memorial to her late husband, George H. Backer. Its cornerstone was laid by Archbishop John J. Glennon on April 15, 1923 and it opened for classes in September of the next year.

The school's new location had been the site of the University's old stadium and athletic field. A later stadium, erected as a memorial to Edward A. Walsh, was completed to the west of the high school in 1930. During the early 1950's Walsh Stadium was razed and its site is now occupied by commercial structures.

St. Louis University High School sustained $150,000 damage in the tornado of September 29, 1927, fortunately without any loss of life. A new wing, containing the chapel and rectory, was completed in 1948, the new gymnasium was opened in 1956 and the latest addition to the high school was finished in 1973. A plan for the enlargement of its grounds is projected.