Tuxedo Park School was founded in 1900, fourteen years after Pierre Lorillard opened his famous park in the Ramapo Hills, 38 miles northwest of New York City. In its early years, the school provided education for the students from Tuxedo Park and coordinated the curriculum with the New York independent schools that some students attended during the winter.

After many years as a proprietary school, Headmaster Anthony Barber led the school into the modern era by obtaining the Charter from New York State and establishing the school as a not-for-profit educational institution.

The school has occupied three different houses in the Park. In 1957, it moved to its present location at Blairhame, the estate of John and Natalie Blair. This elegant English country manor house, designed by Carriere and Hastings, was constructed with the most modern standards of 1915 with a concrete and steel interior structure and elegant wood finishings, many imported from England.

A major building program in 1967 produced the Mattes Wing that currently houses the Primary School and gymnasium. The Second Century Capital Campaign, completed in 2002, endowed two faculty chairs, partially endowed tuition assistance, doubled the Faculty Incentive Endowment, and provided the funds for the new Middle School Wing and gymnasium that opened in the fall of 2003.

The School has maintained its strong traditions of thorough preparation for secondary day and boarding schools while making sure each child is known, appreciated, and has many opportunities to participate and lead.

Three-quarters of the students come from outside Tuxedo Park. The school provides bus transportation from northern Bergen County, New Jersey, and has bus routes extending north and west of the school into Rockland and Orange County. A strong tuition assistance program insures that the school will be accessible to families of modest means.

James Burger, the tenth headmaster of TPS, was appointed in 1994 and retired in 2011.  In addition to many capital improvements made under Burger's tenure, the school benefitted from his leadership in bringing in more qualified faculty and establishing a program of professional development and evaluation, establishing endowed funds, increasing tuition assistance, installing solar panels that provide the school with 1/3 of its electricity annually, and increasing enrollment.

The current Head of School, Kathleen McNamara, came to TPS in the summer of 2011 with 22 years of independent school experience.