Town Leadership
The Chester Town Administrator’s Office
The Town Administrator
Andrew Alward
When a road goes unplowed or a culvert washes out on Route 20, the person with the most operational control over the response is appointed, not elected. Andrew Alward is Chester’s Town Administrator, hired by the three elected members of the Select Board to run the town day to day, and they can let him go if they lose confidence in him. He is the town’s chief administrative officer: he helps supervise the departments, shapes and presents the annual budget, and carries the town’s biggest spending requests to Town Meeting for the final vote. In a town of about 1,228 people the whole office is small, so the same person who answers the phone about a tax bill is often the one drafting the warrant for the next Town Meeting. Because Chester hands the daily machinery to an appointed administrator, the plan to fix a problem usually crosses his desk first, then goes to the board and to Town Meeting, where the registered voters in the room decide it. The Administrator serves under contract and works out of Town Hall alongside an administrative assistant and the town’s clerk, treasurer, and collector.
| Role | Town Administrator (chief administrative officer) |
|---|---|
| Selection | Appointed by the Select Board under contract, not elected |
| Office | Town Hall, 15 Middlefield Road, Chester, MA 01011 |
| Phone | (413) 354-7760 |
| Website | townofchester.net |
What the Town Administrator Does
- Runs the departments. Police, fire, highway, health, and the rest work under the Town Administrator and the Select Board day to day.
- Builds the budget. Each year the Administrator proposes how the town will spend its money, then defends that plan before the Select Board and Town Meeting, which holds the final vote.
- Answers to the board. The Administrator serves at the pleasure of the elected Select Board and carries out the policies it sets.
- Reports to Town Meeting. Major spending and bylaws still need the vote of Town Meeting, and in Chester that means every registered voter who walks in.
The Administration
- Department heads carry out policy, from plowing snow on Route 20 to keeping the town’s electric light and water systems running.
- The Select Board is the check: it hires and can replace the Administrator, sets policy, and signs the warrants that put questions before Town Meeting.
- Boards and commissions, many of them appointed by the Select Board, decide questions like zoning, conservation, and public health.
Contact & Engage
- Town Hall: 15 Middlefield Road, Chester, MA 01011.
- Town Administrator’s Office: (413) 354-7760.
- Report a problem: potholes and road washouts go to the Highway Department at (413) 354-2276.
- Show up: the Select Board meets every other Monday at 6:00 PM at Town Hall, and the public is welcome.
Want to weigh in on a town decision? Learn how to contact your officials so they actually hear you.
MassCivics last checked this page on September 26, 2026.
Sources
- Town records: Town of Chester, Highway Department, as of September 24, 2026.
- Town records: Town of Chester, Select Board, as of September 24, 2026.