On May 1 of that year the New York Yearly Meeting purchased a house and ten acres from Joseph Mabbet, a Quaker from Connecticut, for 1600 pounds, a down payment of 214 pounds was made from the donors, Tripp Mosher, Isaac Thorn, William Thorn, Joseph Talcott, Shadrach Richetson and Jonathan Deuel.

The school's first superintendent was R. Tripp Mosher, and its first principal was Jonathan Talcott, a children's book publisher.

[5] Another teacher and former pupil was Lucretia Coffin Mott, who entered the school at age thirteen in 1806 and graduated in 1810.

Lucretia later led abolition and women's suffrage campaigns as well as working as a teaching assistant.

[8] On January 2, 1917, a fire damaged the upper levels of the main building, prompting the Board of Managers to consider the school's future.

Although proper buildings were not ready on its opening day, the school was quickly reorganized to comply with the regulations of the state.

[9] The large racehorse stables were converted into the main building, with the upper floors as the girls' dormitory.

[10] In the summer of 1920 a two-story structure began to be built, but there were not funds to complete it, so they used two army barracks from the first world war and attached them to both sides of the preexisting building.

This was described in a 1921 article in the Oakwood Bulletin: "As temporary quarters for boys, two army barracks have been secured and are to be joined to a permanent, bell-built center.

The two army barracks were transported to the campus by train from Massachusetts, the school having purchased them directly from the US Government.

The building last served as a gym in 1959 when it was converted into what was called the Fine Arts and Student Recreation Center.

Also that year, the Wallace Dempster Williams Library was established, and opened in early 1930 in the Main Building.

In 1931, the school had "six cows producing 75 qts milk per day, ten pigs, sixteen head of sheep and twelve lambs."

Enrolled as an eighth grader, he went on to graduate in 1938.Twenty years after the move to Poughkeepsie, the school underwent a major renovation that significantly changed the exterior of the main building.

Other speakers included Dorothy Canfield Fisher and a telegram from former president Herbert Hoover was read.

Principal William Reagan noted, "Many changes have taken place in this community and in this nation in the intervening 150 years.

Its home community - as well as the administration and alumni - expects the next 150 years to show comparable progress at Oakwood.” The event also began a fundraising campaign to construct a girls’ dormitory on campus and to pay off the mortgage on the property.

Starting with the renovation of the first floor of the Main Building and in 2015 the school unveiled a two-acre solar array field, making it fully sufficient on renewable energy.