Town Edition
Berkshire County
Windsor, Massachusetts
The fiber optic line running to a house in Windsor is town property. When the cable companies decided these hills held too few customers to bother wiring, Windsor put about $300,000 of its own savings into a $2.3 million network, took on the debt, and lit it up in 2020, so the wire that carries your homework belongs to you and every other taxpayer in town. A town of about 831 people voted to become its own internet company, which tells you something about how Windsor decides things: in a room, by the neighbors who showed up. This guide shows you how to be one of them.
Windsor at a Glance
Sources: Massachusetts DESE, school and district profiles · US Census Bureau (data.census.gov).
- County: Berkshire. Windsor sits high in the Berkshire hills of central Berkshire County, spread across about 35 square miles of highland, forest and farm, and it is home to Notchview, a 3,100-acre reservation of the Trustees of Reservations.
- Government: open Town Meeting, with an elected three-member Select Board and an appointed Town Administrator, Madeline Scully.
- Schools: Windsor is one of seven towns in the Central Berkshire Regional School District, about 1,530 students, led by Superintendent Michael Henault.
How Windsor’s Government Works
Windsor runs on an open Town Meeting, which means there are no elected Town Meeting members at all: every registered voter in Windsor 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 Windsor sends one member to 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 Windsor 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
A 15-member regional committee for the seven-town Central Berkshire district. Windsor holds one seat. It sets school policy, approves the school budget, and hires the Superintendent.
- Residents elect the three members of the Select Board and Windsor’s seat on the regional 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 Monday evenings from 7 to 9 pm at the Windsor Town Offices, 1890 Route 9, weekly or every other week. 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 most recent Annual Town Meeting was on May 4, 2026.
- Town elections: Windsor votes in the spring, with the most recent annual town election on May 11, 2026.
- State and federal elections: even-numbered years. The 2026 primary and general are this fall.
Explore the Windsor 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.
- Windsor HistoryGageborough, the hills, and Notchview
- DemographicsWho lives in Windsor
- Non-ProfitsCommunity organizations
- Student DataCentral Berkshire 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 Berkshire County, and that includes Windsor. 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 Windsor
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 regional School Committee. The budget and bylaws are voted by Town Meeting.
- Find the meeting. The Select Board meets Monday evenings at the Windsor Town Offices, 1890 Route 9, 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 to see how to sign up.
- Or skip the trip. Report a pothole, a washed-out dirt road, or a drainage problem to the Highway Department, which owns the repair.
- Town Offices: 1890 Route 9, Windsor, MA 01270. Main line 413-684-3811.
- Town Clerk & agendas: Town Clerk Aline Ferris, 413-684-3811, with meeting agendas and minutes posted at windsormass.com.
- Public schools: the Central Berkshire Regional School District, cbrsd.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.