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Holliston is a New England town in Middlesex County, Massachusetts, United States in the Greater Boston area. The population was 14,996 at the 2020 census. It is located in MetroWest, a Massachusetts region that is west of Boston. Holliston is the only town in Middlesex County that borders both Norfolk and Worcester counties.

At the time of the earliest European settlements, where Holliston exists now was part of the territory of the Awassamog family of Natick (the first Nipmuc Praying Town), who also held authority over land near Waushakum Pond at Framingham and land near Annamasset at Mendon. In 1701, a large tract of land that included the west half of Holliston, eastern Milford and parts of Hopkinton and Ashland was given to the local Nipmucs in a land exchange with Sherborn. Their ownership of the tract was brief, as settlers purchased tracts of land there until all traces of Nipmuc presence disappeared. The Nipmuc village of Mucksquit (translation – “place of much grass”), located on the shore of Wennakeening (translation – “smile of the great spirit”) was near the site of the Morse family farm, today known as Lake Winthrop. The Morses, Sheffields, Marshalls and Bullards and many others followed Pout Lane (an old Native American foot-path, now partly modern day Rte 16 and Highland St., respectively) out to the new territory and settled along the path, thus forming a cluster of farms that would eventually become Holliston. John Eliot and Daniel Gookin (Christian missionaries) also followed the path in search of converts to Christianity and encouraged the Nipmucs to gather into villages, which made their task of finding them easier. Though not as famous as the Bay Path or the Old Connecticut Path, Pout Lane played a major role in the settlement of Holliston and other points southwest of Boston. Holliston, then part of Sherborn, was first settled by Europeans in 1659 by Massachusetts Bay Puritans. The town of Holliston was incorporated on December 3, 1724, by virtue of approval by the General Court petition requesting that “the western part of Sherborn be a Town.” The name was taken in honor of Thomas Hollis of London, a benefactor of Harvard College. The first town meeting was held at the house of Timothy Leland on December 23, 1724, “at which five selectmen and all other required officers were chosen.” The town has grown from a community of a few hundred residents setting aside ten pounds per year for public education to a community of over 13,000 with an annual budget of over $40 million including more than $23 million for a nationally recognized school system.