Cheshire High School 525 S Main St, Cheshire, CT06410 Cheshire High School has about 1,600 students enrolled in grades nine through twelve. Nearly 90 percent of the students…More take the SAT, besting the state and national averages in reading, writing and math. Eighty percent of the graduating students attend college. The school offers 30 athletic programs and has 26 clubs. The Cheshire Music Program has been ranked as one of the top 100 in the United States.