Town Edition
Hampden County
Chester, Massachusetts
Chester’s Town Hall at 15 Middlefield Road does two jobs. Every other Monday evening the Select Board runs the town from that room, and every summer since 1990 the Chester Theatre Company turns the same room into a professional stage. On May 2, 2026, 246 Chester voters filled a Select Board seat, a Gateway Regional School Committee seat, and the office of Town Moderator in a single afternoon, and in a town of about 1,228 people that is most of the reason the place runs the way it does. Chester has governed its own affairs this way since it was set off as Murrayfield in 1765 and renamed Chester in 1783. This guide shows you how to get into the room.
Chester at a Glance
Sources: Massachusetts DESE, school and district profiles · US Census Bureau (data.census.gov).
- County: Hampden. Chester sits in the Berkshire foothills of western Massachusetts, and the West Branch of the Westfield River runs down through the village center.
- Government: open Town Meeting, with an elected three-member Select Board and an appointed Town Administrator, Andrew Alward.
- Schools: the Gateway Regional School District, about 721 students across six member towns, led by Superintendent Melissa Matarazzo.
How Chester’s Government Works
Chester runs on an open Town Meeting, which means there are no elected Town Meeting members at all: every registered voter in Chester is a member, and any of them can walk in, speak, and vote on the budget. Voters also elect a three-member Select Board to set policy between meetings, and they help elect the regional School Committee that oversees the schools. The Select Board 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 Select Board, 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 Chester is a member. Town Meeting adopts the annual budget, passes town bylaws, and approves major spending. This is direct democracy in its literal sense.
Select Board
Three 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 Select Board. Hired under contract, not elected.
School Committee
Fifteen members, elected by the voters of the six-town Gateway Regional district. It sets school policy, approves the school budget, and hires the Superintendent.
- Residents elect the three members of the Select Board and Chester’s seats on the School Committee.
- The Select Board 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: register at 16, vote at 18, and once you are registered you are already a member of Town Meeting.
Civic Calendar
- Select Board: meets every other Monday at 6:00 PM at Chester Town Hall, 15 Middlefield Road. The agenda is posted in advance, so check the town calendar before you go.
- Town Meeting: the Annual Town Meeting is held in the spring, and the town can call a Special Town Meeting when business cannot wait. The 2026 Annual Town Meeting was held on June 8, 2026.
- Town elections: Chester votes on the first Saturday of May. The 2026 annual town election was held on May 2, and drew 246 ballots. The next is in spring 2027.
- State and federal elections: even-numbered years. The 2026 primary and general are this fall.
Explore the Chester Edition
- Town Administrator’s OfficeThe town’s chief administrator
- Select BoardYour three board members
- School CommitteeSuperintendent & committee
- Town DepartmentsWho does what at Town Hall
- Boards & CommissionsWhere residents serve
- LegislatorsYour voice in Boston & D.C.
- Chester HistoryMurrayfield, the railroad, and 1783
- DemographicsWho lives in Chester
- Non-ProfitsCommunity organizations
- Student DataGateway schools by the numbers
Your County Officials
Two of the people with the most direct power over your life are elected countywide. The district attorney decides who gets charged with a crime, and what they get charged with. The sheriff runs the county jail. Both of them answer to the voters of Hampden County, and that includes Chester. They appear on your ballot. Now you know what to look for.
Every county in Massachusetts elects its own, and 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.
Your First Civic Action in Chester
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 Select Board. Schools go to the School Committee. The budget and bylaws are voted by Town Meeting.
- Find the meeting. The Select Board meets every other Monday at 6:00 PM at Chester Town Hall, 15 Middlefield Road, and the agenda is posted in advance.
- Know your members. All three Select Board 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 washed-out road, or a plowing problem to the Highway Department, which owns the repair.
- Town Hall: 15 Middlefield Road, Chester, MA 01011. Select Board office (413) 354-7760.
- Town Clerk & agendas: (413) 354-6603, with meeting agendas and minutes posted at townofchester.net.
- Public schools: the Gateway Regional School District, 413-685-1000, grsd.org.
Local government works best when residents show up. Find your Select Board, speak at a meeting on the town’s published calendar, or simply register to vote and take your seat at Town Meeting.