With ivy growing on its brick walls, the building that houses Winchester's high school students has a classic feel to it. Led by Principal Tom Gwin, the school's objective is to provide its students an opportunity to achieve excellence in learning.

Winchester High School's mission is to cultivate critical thinking, clear and effective communication, intellectual creativity, a sense of personal, civic and social responsibility and an ability to apply these skills and knowledge to life situations in all its students.

The school has 29 clubs and extracurricular activities students can join, along with 27 varsity athletic teams.