In 1634 Benjamin Syms left 200 acres (0.81 km2) and eight cows to provide a free school for children of the parish.

In 1659 Thomas Eaton, a 'cururgeon' (surgeon), left 500 acres (2.0 km2), buildings, livestock, and two slaves for a school to serve Elizabeth City County.

From the early 20th century, Hampton High was ranked in the top ten of schools in Virginia, and the West Point Military Academy acknowledged that it accepted Hampton graduates without requiring them to take the West Point entrance exam.

The school was featured in national news in the summer of 1995 for the celebration of the centennial graduating class (1996).

[4] In March 2019, for the first time in Hampton's history, the Band and Chorus earned Superior ratings at State Assessments, establishing Hampton High School as Blue Ribbon School, which is the highest musical honor a Band and Choral program can receive.

[5] Hampton High School is ranked the #10 dynasty in the country in the history of football, 836 wins.

The Hampton High boys' team finished first in the district in the 2011-2012 season going on to win the AAA state championship.

After finishing second in the PD Regular Season and Tournament, the Crabbers advanced to the regional meet and placed third, losing to frequent regional-champion Princess Anne High School by a mere 15 points — one question away from qualifying for the VHSL State meet.

[7] In 2011, the Hampton High School Drama Club competed in the District One Act Play competition, where they were second only to Menchville.

In spring 2012, the Symphonic Band earned straight superior ratings at State Concert Assessment in all categories from all four judges for the second year in a row.

The bands earned Grand Championships at the Menchville Monarch Competition, the Hermitage Classic, and the Hanover Hawks Marching Invitational.

For four consecutive years, from 2010 to 2013, the Pride of the Peninsula has been the highest scoring band out of the City of Hampton at the annual Holiday Parade.