Cheshire, Massachusetts

Photo: John Phelan, CC BY-SA 4.0, via Wikimedia Commons.

When Thomas Jefferson won the presidency, the farmers of Cheshire pooled a full day’s worth of curds, pressed them into a cheese that weighed 1,235 pounds, and sent it on a month’s journey to Washington, where it was presented to him at the White House on New Year’s Day of 1802. The Cheshire Mammoth Cheese was a small town making itself heard, and two centuries later the town still runs on that same habit. Neighbors gather in one room at Town Meeting on the second Monday in June, raise their cards, and turn what they decide into law. This guide shows you how to get into that room.

Cheshire at a Glance

3,258Residents (2020)

1793Incorporated

5Board of Selectmen Members

992District Students

Sources: Massachusetts DESE, school and district profiles · US Census Bureau (data.census.gov) · Town of Cheshire.

County: Berkshire. Cheshire sits in the northern Berkshires between Mount Greylock, the highest point in Massachusetts, and the Hoosic River valley, with the Cheshire Reservoir and the Ashuwillticook Rail Trail running through it.
Government: open Town Meeting, with an elected five-member Board of Selectmen and an appointed Town Administrator, Jennifer Morse.
Schools: the Hoosac Valley Regional School District, about 992 students shared with the neighboring town of Adams, led by Superintendent Aaron M. Dean.

How Cheshire’s Government Works

Cheshire runs on an open Town Meeting, which means there are no elected Town Meeting members at all: every registered voter in Cheshire is a member, and any of them can walk in, speak, and vote on the budget. Voters also elect a 5 member Board of Selectmen to set policy between meetings and the School Committee that oversees the schools. The Board of Selectmen hires a professional Town Administrator to run the town day to day. So the money is voted by whoever shows up, the direction is set by the Board of Selectmen, and the daily work is carried out by the Town Administrator.

Town Meeting

The legislative body, and it is not a committee. Every registered voter in Cheshire is a member. Town Meeting adopts the annual budget, passes town bylaws, and approves major spending. This is direct democracy in its literal sense.

Board of Selectmen

5 members elected town-wide. They set policy, sign the warrants that decide what reaches Town Meeting, appoint residents to many town boards, and hire and supervise the Town Administrator.

Town Administrator

The appointed chief administrator. Runs the departments, builds the budget, and answers to the Board of Selectmen. Appointed, not elected.

School Committee

7 members, elected by the voters of the district the schools serve. It sets school policy, approves the school budget, and hires the Superintendent.

Residents elect the 5 members of the Board of Selectmen and the School Committee.
The Board of Selectmen hires the Town Administrator and decides what goes on the Town Meeting warrant.
Town Meeting votes the budget and the bylaws, and every registered voter present can vote.
You take part: pre-register at 16. A pre-registrant is on the list but is not allowed to vote yet. Once you turn 18 that designation comes off on its own and you are a registered voter in Cheshire, which makes you a member of Town Meeting with a vote on the floor. If you never pre-registered, register with the Town Clerk, and do it well ahead: the rolls close at 5 p.m. on the tenth day before any election or Town Meeting.

Civic Calendar

Board of Selectmen: meets at 6:30 p.m. in the Meeting Room at the Community House and Town Offices, 191 Church Street. The agenda is posted in advance, so check the town calendar before you go.
Town Meeting: the Annual Town Meeting is held on the second Monday in June, and the town can call a Special Town Meeting when business cannot wait.
Town elections: the annual town election is held on the first Monday in May. The next one comes around in May 2027.
State and federal elections: even-numbered years. The 2026 state primary was held on Tuesday, September 1, and the general election is on Tuesday, November 3, 2026.

Explore the Cheshire Edition

Your County Officials

Two of the people with the most direct power over your life are elected, and neither one sits on Beacon Hill. The district attorney decides who gets charged with a crime, and what they get charged with. The sheriff runs the county jail. The sheriff is elected by the voters of Berkshire County. The district attorney is elected by the voters of a prosecution district, and Massachusetts draws eleven of those across its fourteen counties, so a district attorney’s territory does not always follow a county line. Both appear on your ballot in Cheshire. Now you know what to look for.

District Attorney, Berkshire District

Timothy J. Shugrue

In office since 2023
Official site

Sheriff, Berkshire County

Thomas Bowler

In office since 2011
Official site

Massachusetts elects fourteen sheriffs, one for each county, and eleven district attorneys, one for each prosecution district. The job is the same everywhere: the charging decisions, the jail. Look up any town in the state and see who holds these two offices there.

Officials for any Massachusetts town

Your First Civic Action in Cheshire

You do not have to wait until you can vote to be heard in your own town. Here is how to take a real concern to the people who decide.

Pick the right body. Town policy, roads, and police or fire go to the Board of Selectmen. Schools go to the School Committee. The budget and bylaws are voted by Town Meeting.
Find the meeting. The Board of Selectmen meets at 6:30 p.m. at the Community House and Town Offices, 191 Church Street, and the agenda is posted in advance.
Know your members. Five Board of Selectmen members are elected town-wide, so every one of them answers to you.
Speak. Meetings are open to the public and residents may address the board. Check the agenda for how to sign up.
Or skip the trip. Report a pothole, a broken light, or a water problem to the Department of Public Works, which is the department that owns the repair.

Town Hall: Community House and Town Offices, 191 Church Street, Cheshire, MA 01225. Board of Selectmen office (413) 743-1690 ext. 100.
Town Clerk & agendas: (413) 743-1690 ext. 104, with meeting agendas and minutes posted at cheshire-ma.gov.
Public schools: the Hoosac Valley Regional School District, central office (413) 743-2939, hoosacvalley.org.

Local government works best when residents show up. Find your Board of Selectmen, speak at a meeting on the town’s published calendar, or simply register to vote and take your seat at Town Meeting.

Meet Your Board of Selectmen

Take Action in Your Town

MassCivics last checked this page on September 26, 2026.

Sources

Population and demographics: US Census Bureau, Census profile of Cheshire town, Berkshire County (American Community Survey 5-year estimates 2020-2024 and the 2020 Census), as of April 1, 2020.
Schools and districts: Massachusetts DESE, Hoosac Valley Regional district profile, Enrollment Data (2025-26), as of October 1, 2025.
Schools and districts: Massachusetts DESE, Hoosac Valley Regional district profile, contact information (2025-26), as of October 1, 2025.
Elections and voter enrollment: Secretary of the Commonwealth, candidate profile, Thomas N. Bowler, as of November 8, 2022.
Elections and voter enrollment: Secretary of the Commonwealth, candidate profile, Timothy J. Shugrue, as of November 8, 2022.
Town records: Town of Cheshire, About, History, written by Barry Emery, as of March 14, 1793.
Town records: Town of Cheshire, Board of Selectmen, as of September 23, 2026.
Town records: Town of Cheshire, Town Administrator, as of September 23, 2026.
Town Clerk records: Town of Cheshire, Elections, as of April 24, 2026 and September 1, 2026.
Town Clerk records: Town of Cheshire, Town Clerk, as of May 4, 2026, June 8, 2026 and September 23, 2026.
School district records: Hoosac Valley Regional School District, School Committee members, 2026-2027 School Year, as of September 14, 2026.