Mt. Pleasant Military Academy was established in 1814 for the purpose of providing in Ossining a school of the first order, where young men might be prepared for college, or for active business life, and where the influences thrown around the students should be such as to develop courteous and manly men.
Money for the establishment of the school was raised by contributions from public spirited men of Westchester County, New York and elsewhere. The first contribution was made on November 13, 1813, and up to August, 1831, the sum of $1,083.81 had been contributed. It would seem, therefore, that almost from the start the school had been self-sustaining. The first name on the list of contributors is that of Daniel D. Tompkins, Governor of the State of New York from 1807 to 1817 and Vice President of the United States from 1817 to 1825.
It was characteristic of the man that in the midst of his herculean tasks as defender of the State during the second war with England, he could find time to devote some attention to the little school at Mount Pleasant. It is said of Tompkins that he "did more than the Federal Government for the success of the operations on the Canada–US border, pledging his personal and official credit when the New York banks refused to lend money on the security of the U.S. Treasury notes without his endorsement. He advanced the means to maintain the military school at West Point, to continue the recruiting service in Connecticut, and to pay the workmen that were employed in the manufacture of arms at Springfield". But he did not overlook the movement for better education in his native county.
There is scant record of the conduct of the school from 1814 to 1820, but on March 24 of that year an act was passed in the Legislature of New York, incorporating Mount Pleasant Academy and from that time on have been preserved full and complete records of the school. The worthy aims of the school are quaintly set forth in an advertisement printed in the "New York Commercial Advertiser" for April 28, 1823, over the signature of General Aaron Ward, Secretary of the Board of Trustees and one of the original incorporators of the Academy. General Ward says in part: "In this Seminary the academic year will commence the 1st of May next. The Trustees, therefore, respectfully beg leave to recommend it to the public, as an institution where youth are taught, by easy graduation, from the first rudiments of knowledge to the higher classics, sufficient to qualify them for admission into any of the American colleges, and more particularly for Columbia College, in the City of New York; or prepare them for the various stages of life. The Academy is pleasantly situated on the banks of the Hudson, within 33 miles of the City of New York, in a healthy village, possessing many local advantages, among others a daily communication with the city, either by land or water; good medical advice, and the use of several churches." Even today we need add little to these quaint words except possibly to say that daily communication with the city has been replaced by an hourly train service. But the village boat still leaves its dock in the early morning, returning from the city with the lengthening shadows of evening.