[4] As quoted by Winslow's former Principal Doug Carville, the school's "philosophy is to tailor education to meet the needs of each individual.

We have a safe and friendly school climate where the administration, faculty and staff are committed to students of all ages".

These activities include, Fall Musical Jazz Band Math Team National Honors Society Theater Program Anime Club Pep Band Renaissance Service Club One Act Spring Play Student Senate Art Club Black Raider News Club Yearbook Staff Lettuce Club The Economics classes also nominate the top eight performers to compete in the State Economics Meet, with the top four as the A Team, and the other four as the B Team.

Sophomore students can choose to participate in setting up the Sadie Hawkins Dance, which that class pays for, while Juniors, whose class pays for the Prom, can choose to join the Prom Committee, which takes place in May.

Sung to the tune of the American Navy's Song, Anchors Aweigh, Winslow's school song is, Stand loyal to our school Our Winslow High We'll all unite and send our Cheers up to the sky.