Holliston, Massachusetts
A Short History of Holliston
A footpath out of Sherborn, a town named for a Londoner who never saw it, the biggest shoe town in the country, and a neighborhood that has been arguing with California about a poem printed in 1888.
1724, and the Village That Left
Holliston did not begin as a town. It began as the western part of Sherborn, and by the 1720s the farms out there were far enough from the meetinghouse that the settlement wanted its own. On December 3, 1724 the General Court approved a petition asking that the western part of Sherborn be a town, and Holliston existed. The name went to Thomas Hollis of London, a benefactor of Harvard College who had nothing else to do with the place. Twenty days later, on December 23, 1724, the first town meeting was held at the house of Timothy Leland, and it chose five selectmen and all the other officers the town needed.
Read that last sentence again, because it is the oldest continuous fact in this guide. The town’s first act was a town meeting that elected a board of selectmen. Three hundred and two years later Holliston still runs on an open Town Meeting and still elects the board that runs the town between meetings. What changed is the size and the name: five selectmen then, a three member Select Board now.
Before the Town
The land was not empty when Sherborn’s farmers walked out to it. It belonged to the Awassamog family of Natick, the first Nipmuc praying town, and the Nipmuc village of Mucksquit, a name meaning place of much grass, stood on the shore of a lake they called Wennakeening. That lake is now Lake Winthrop, and the town beach is on it. The route the first farms followed was an old footpath called Pout Lane, and parts of it are now Route 16 and Highland Street. When you drive Route 16 through Holliston you are on a road that was a path before it was a road, and the town’s own street map still carries a Pout Lane.
The Shoe Town
Holliston was once the largest producer of shoes in the United States. Not one of the largest. The largest. The Goodwill Shoe Company was the biggest of the makers, and its empty factory buildings still stand on Water Street, where many of them are now artists’ studios. The town’s own About page adds two more claims from that era: that Holliston is famously known for inventing the steel-toed boot, which was produced in the Old Mill Building, and that early residents worked on the railroad and made straw hats and brooms.
The railroad in that sentence is the same one this whole guide keeps coming back to. The Boston and Albany’s Milford line ran through the middle of Holliston, carried the shoes out and the workers in, and when it died the town spent twenty years and more than $1.4 million of its own Community Preservation money buying the ground back. What the trains left is now a walking path.
Mudville, and a Century of Arguing With Stockton
One Holliston neighborhood is called Mudville, and it claims to be the Mudville of Ernest Lawrence Thayer’s 1888 poem Casey at the Bat. Stockton, California claims the same thing. Neither side has produced anything that settles it and neither side has conceded. It is a small thing and it is a real one: a place is partly what its residents insist it is, and Holliston keeps insisting.
2024: The Town Rewrote Its Own Government
Here is the piece of Holliston history that most directly affects you, and it is two years old. From 1994 until 2025 the town ran under Chapter 94 of the Acts of 1994, which had created a Select Board and Town Administrator form. In May 2024 an article to replace it with a Town Manager act came to Annual Town Meeting and was indefinitely postponed. The Select Board spent August and September going back to the separately elected boards and committees, changed three sections of the draft, and brought it to Fall Town Meeting in October 2024 as Article 8. That time it passed.
Then it went to Beacon Hill, because a Massachusetts town cannot change its own form of government alone. Representative James C. Arena-DeRosa of Holliston filed it as House Bill 5119, the House passed it on December 19, 2024, the Senate on December 30, and the Governor signed it on January 10, 2025 as Chapter 405 of the Acts of 2024. Its first section repealed the 1994 act outright. Four months later the Select Board announced Holliston’s first Town Manager.
From the October vote to the Governor’s signature took under three months, and Holliston had its first Town Manager on the job by June. The whole sequence started with a vote in a hall, in a room where every registered voter in town was entitled to stand up and speak. That is the machinery this guide is about, and Holliston used it recently enough that people who were in the room are still on the boards.
The History the Town Keeps Itself
The Holliston Historical Society, whose own motto is keeping Holliston’s history alive, holds the town’s records and runs a members’ programme of lectures, portrayals and an annual Father’s Day car show and breakfast. Preservation in Holliston is also a civic process with a budget: the town adopted the Community Preservation Act in 2002, among the first communities in the state to do so, and funds it with a 1.5 percent property tax surcharge plus state matching money. Every project that money pays for is voted at Town Meeting, one article at a time, which means the preservation of Holliston’s history is itself decided in the room where every registered voter can stand up.
Sources: Town of Holliston, About Holliston (townofholliston.us/27); Town of Holliston, Article 8 Special Legislation Town Manager Act (townofholliston.us/536); Chapter 405 of the Acts of 2024 and House Bill 5119, malegislature.gov; the Community Preservation Coalition, The Heart of Holliston; Holliston Historical Society; Wikipedia, Holliston Massachusetts, and the sources it cites; U.S. Census Bureau.