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The Board of Selectmen is the group in town that sets policy and strategic direction, coordinates the activities of other boards, and hears appeals and resolves problems that have not been settled at lower levels. The position of selectman/select board member is steeped in nearly 400 years of tradition. Though they earn only a small stipend, if anything, for their work on behalf of their hometowns, selectmen have played significant roles over the years in shaping the future of their communities. They are looked to – by citizens and local government employees alike – for leadership and integrity, particularly in difficult times. Local government has changed dramatically since colonial times, but selectmen continue to be seen as the leaders of an increasingly complex enterprise.

The office of selectman was not imported from England but evolved here. Early in the history of the Commonwealth, town meetings would periodically “select” prominent citizens to perform the business of the town between town meetings. In 1633, Dorchester (now part of Boston) was the first New England town to organize a local government, choosing 12 men as selectmen. Other Massachusetts towns quickly adopted this unique form of government.

Colonial laws in Massachusetts gave selectmen significant authority over town finances, care of the poor, schools, admission of new residents into the town, roads and other public works, land regulation, local defense, and the appointment of other town officials not elected by the town meeting. In colonial times, most “executive” business of towns was conducted by the Board of Selectmen. As Massachusetts grew and the activities of towns became increasingly sophisticated, selectmen were assigned greater responsibilities and authority while new, independent elected officers and boards were entrusted with specialized functions.

A Board of Selectmen (or select board) operates as a collective decision-making body. The legal authority of selectmen is limited to actions taken by the board at a legally called, posted meeting with a majority of the board present. If a board member wants to accomplish specific objectives, he or she must find a way to work with the other members of the board and with other boards in town.

While Selectmen are the principal administrative officers of the town, other boards, including the School Committee, the Planning Board, and the Board of Health, may wield at least as much authority over certain aspects of town government.

Generally, boards of selectmen have at least several important responsibilities under state law:

  • The power to prepare the town meeting warrant
  • The power to make appointments to town boards and offices
  • The power to employ professional administrative staff and town counsel
  • The power to sign warrants for the payment of all town bills
  • The authority to grant licenses and permits

(from the Massachusetts Municipal Association)

Contact Info

Cheshire Community House/Town Offices
191 Church Street
Cheshire, MA 01225
United States
Google Maps

Phone: (413) 743-1690 x. 100
Email: [email protected]

Hours of Operation:
Meetings are held at 6:30 p.m. in the Meeting Room at the Community House/Town Offices (former Cheshire Elementary School), 191 Church St. The entrance is located at the West End of the building and the entrance is at the ramp.

Board of Selectmen Members


Shawn McGrath

Email: [email protected]

Term Expiration: 2024


Jason Levesque

Email: [email protected]

Term Expiration: 2026


Raymond Killeen

Email: [email protected]

Term Expiration: 2024


Michelle Francesconi

Email: [email protected]

Term Expiration: 2025


Ronald DeAngelis

Email: [email protected]

Term Expiration: 2025

Cheshire Master Plan

Cheshire Master Plan Appendix

Equal Opportunity Employer

  • The Town of Cheshire is an equal opportunity provider and employer and does not discriminate against any applicant because of race, color, religion, sex, marital status, national origin, age, disability, sexual orientation or any other class protected by federal, state or local law.

Financial Management and Operations Policies

Financial Managment Review September 2022


Hazard Mitigation/MVP Process

The Town of Cheshire is creating a Hazard Mitigation and Municipal Vulnerability Prepardness Plan to better prepare for natural disasters.  Help us our by taking less than 10 minutes on the survey below!


MS4 Outreach

The Town of Cheshire was added as an MS4 Community under the 2016 Massachusetts MS4 Phase II General Permit. Cheshire was authorized to discharge within the MS4 Urbanized Area in December of 2021. As a smaller community, the MS4 area covers only a portion of Town surrounding the MassDOT Route 8 North/South Corridor and around Cheshire Reservoir residential areas. 

The MS4 General Permit was created under the Clean Water Act's National Pollution Discharge Elimination System (NPDES) Program to preserve, protect, and improve the Nation's water resources from polluted stormwater runoff. It does so by requiring Towns to fulfill best managment practices in a number of ways within the MS4 Urbanized area (see map below). 

Special Event Permit Application

Tag Sale Ordinance

Town Flag Policy