The first Hilton Schools Regents Diploma student, Jennie Mitchell, graduated in 1899.

In March 2005, as a part of its Capital Bond Project, Hilton added an Aquatic Center at Merton Williams Middle School, replacing the old five-lane pool.

In 2014, the Hilton Cadets Wrestling Team won the Section V Class AA tournament and finished the season ranked fourth in New York State.

The school's Winter Drum Line is a member of the New York State Percussion Circuit, and competes at membership tournaments throughout Western New York, including a competition hosted each winter at Hilton High School.

In 2013, performing their show "Arabian Nights: Legend of Scheherazade", Hilton High School was crowned WGI World Champion in Percussion Scholastic "A" class.