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 Staples intended to fund the school via an interest left in his will; however, that interest became known while he was still alive, and led to the school's foundation being laid in 1884. On April 24, 1884, businesses closed early in Westport to celebrate the dedication of Staples High School. Connecticut Governor Thomas M. Waller attended the opening.