[2] Windsor High School is fully accredited under Virginia's Standards of Learning program.

Windsor High was recognized with the Virginia Index of Performance “Competence to Excellence” Award: 2009 as well as Jostens National Recognition for Yearbook Design.

Windsor High School seniors accumulate over 2 million dollars in scholarships each year.

Dual credit is also offered for core area and career and technical education courses.

Students also frequent the Isle of Wight County Fair each September, the art club competes in the sand castle sculpting tournament at Neptune Festival in Virginia Beach in late September, the cheerleaders compete statewide every year, the marching dukes marching band competes in multiple field show and parade competitions every year, there is a talent show held in the auditorium each year, among many other exciting events that occur at WHS.