The school itself was a gift to the town by Tuxedo Park resident George Fisher Baker, an American banker and philanthropist.

The high school imposed a demanding all-Regents curriculum on students before the New York State Education Department began requiring it.

[3] The Greenwood Lake School Board cited the cost per student at Tuxedo compared to lower bids from Warwick, Goshen and Chester as the primary reason for pulling students from the school.

In an attempt to retain the students, the Tuxedo Board of Education applied to become a STEM charter school which would allow students from Greenwood Lake as well as other neighboring towns to tuition into the school, but this was ultimately rejected by the New York Board of Regents.

At the end Greenwood Lake provided all options other than Tuxedo to their residents and Tuxedo decided to keep the school open despite lower enrollment as it was determined that they would only save between 6-12% by tuitioning students to other schools including Suffern, Ramsey or Northern Highlands.