The town of Leicester was purchased in 1686 by a group of businessmen from Roxbury, MA; it was settled and incorporated in February of 1713. The town’s first name was Towtaid, which was the name given to it by the group of Nipmuc Indians that sold the land. It was later called Strawberry Hill, because wild strawberries grew in great quantities. The name Leicester was finally decided upon because it was where the father of the first selectman, Thomas Green, came from.
Leicester began as a farming community but by the start of the American Revolution numerous mills had been established to complement the local farming industry. Leicester soon became a center for the manufacture of hand cards, which are tools for straightening fibers prior to spinning thread and weaving cloth.

The term “Minuteman” originated with Leicester's, Colonel William Henshaw declaring at a 1774 meeting of the Committee on Safety that “we must have companies of men ready to march upon a minute’s notice.
Leicester is also home to a confirmed site on the Underground Railroad. Rev. Samuel May, who was pastor of the Unitarian Church, was asked to step down from his post because his mill-owning parishioners felt that he was devoting too much time to his position as Secretary of the Massachusetts Anti-Slavery Society. After his death Booker T. Washington with members of the Tuskegee Institute delivered a speech on May's work on the steps of the same church that May had been asked to leave.
Colonel Thomas Denny, Jr. commissioned Ralph Earle, an American painter, to paint the view from his home on Denny Hill. Colonel Denny wanted to take a memento of this view the he had enjoyed since childhood. Twelve Oaks at Stafford is situated on Denny Hill and that magnificent view is still the same. The painting is on view at The Worcester Art Museum.
The end of Leicester's textile industry came in 1991 with the closing of Worcester Spinning and Finishing in Cherry Valley. The textile industry is gone from Leicester but there are many reminders of its past. These are the legacies of Leicester’s past.
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