The present Westborough High School, with a capacity of 1,000 students, was built in 1968 on 30 acres in the heart of Westborough. The school's location has a rich history. Around 1675 the town's first settler, Thomas Rice, built his garrison home on this site. In 1704, Canawaugha Indians from Canada swooped down Grindstone Hill (behind the present school) and captured five Rice boys while they were gathering flax near the brook. The eldest, Timothy Rice, was raised as a native American and eventually became a sachem of the Iroquois nation.

On this land, in the mid-1800's, Christopher Whitney, owner of a box factory and Whitney Hotel, built his mansion, which became a local showcase. In the early 1920's, the Aronson cattle dealers bought the property and held regular cattle auctions there. The home, unfortunately, lay in the path of the devastating 1953 tornado; when the tornado struck the house and fields, three Aronson family members and a hired man lost their lives.

The first high school in Westborough had been built in 1854 on Science Hill on School Street. Before this time, those wishing to continue their education beyond the district one-room schoolhouse would study with a tutor or in a private school. The first high school teacher, Silas Stone, taught 20 subjects, including Greek and astronomy to about 25 students. Not many young people went on to high school, since most were needed to work on the family farm or in local factories. The high school eventually became graded and offered two courses of study: Classical and English. In 1872, the first seniors graduated; there were three in that graduating class.

The need for a modern high school, complete with laboratory, gym, and industrial arts facilities, drew the attention of Frank and Fannie Forbes, major Westborough philanthropists. The Forbes built and presented to the town a new high school in 1926, on the site of the former Whitney Hotel. This 14-room school (now the Municipal Building) served as the Town's high school and junior high until 1956, when a new high school was built on Fisher Street. The growth in the school population called for another move in 1968 to the current well-equipped facility.