Seeing the “town’s lack of progress in education” Horace Staples a wealthy businessman with interests in shipping, hardware sales, and banking, founded Staples High School.Initially Horace Staples intended to fund the school via an interest left in his will; however that interest became known whilst Horace was still alive and led to the high school’s foundation being laid in 1884.It was reported that on 24 April 1884 businesses closed early in Westport to celebrate the dedication of Staples High School.Connecticut Governor Thomas M. Waller attended the opening.

Front of Staples High School

In the first year of operation, commencing in the fall of 1884, Staples High School had 60 students of the 807 students attending schools in Westport.

On June 24, 1887 Staples High School conferred its first high school diplomas to six female students that comprised its first graduating class.

In 1909 the Town of Westport accepted control of Staples High School from the Horace Staples estate.