Employment Opportunities
Custodian
The Town of Cheshire is accepting applications for the position of Custodian.
Under the supervision of the Department of Public Works the person is responsible for physical and manual work involving cleaning and care of municipal buildings and associated grounds and all other related work and/or building as required and assigned.
The position is part-time (10 Hours Per Week) with flexible hours. This position is unbenefited.
Job description and application forms available at www.cheshire-ma.gov. Applications and Résumés will be accepted until the position is filled. Mail responses to Town of Cheshire, Town Administrator, 191 Church Street, Cheshire, MA 01225, or email [email protected] . AA/EOE.
Posted 9/16/26
Department of Public Works
Water Operator/Laborer
The Town of Cheshire is accepting applications for a full-time benefit eligible DPW Water Operator/Laborer. The DPW Water Operator/Laborer performs skilled work in management, operation and preventative maintenance of the town water system. The position assists with maintaining municipal streets and roads including removal of snow, performing routine building maintenance, preventative maintenance, physical and manual work involving the care of municipal buildings and associated grounds.
High school diploma or equivalent and at least one year of related experience; or any equivalent combination of education, training, certification and experience. Must have a valid Massachusetts Driver’s License, ability to pass a CORI check, ability to pass a DOT physical and maintain a DOT medical card. Must possess Massachusetts Drinking Water Grade D1/T1 Operator in Training Licenses, Backflow Prevention Device Testing Licenses. Operator in Training must be completed within two years of hiring.
The candidate must possess a willingness to work overtime during the winter months and during times of emergencies on short notice.
Job description and application forms available at www.cheshire-ma.gov. Applications and Résumés will be accepted until the position is filled. Mail responses to Town of Cheshire, Town Administrator, 191 Church Street, Cheshire, MA 01225, or email [email protected] . AA/EOE.
Posted: 9/16/26
DPW Water Operator/Laborer Job Description
Town of Cheshire
Department of Public Works
Highway- Heavy Equipment Operator
The Town of Cheshire is accepting applications for a full-time benefit eligible DPW Highway- Heavy Equipment Operator . The DPW Highway- Heavy Equipment Operator performs manual work including the maintenance and cleanliness of municipal streets and roadways, operating heavy trucks and machinery, performing a variety of operation, maintenance, repair duties, snow and ice removal and ensuring proper working condition of equipment, vehicles and other property owned by the Town.
High school diploma or equivalent and at least one to three years of related experience; or any equivalent combination of education, training, certification and experience. Must have a valid Massachusetts Driver’s License, ability to pass a CORI check, ability to pass a DOT physical and maintain a DOT medical card. A CDL Class B with air brake endorsement and a Hoisting 2A license is required at the time of hire, or the ability to obtain within six months of hire.
The candidate must possess a willingness to work overtime during the winter months and during times of emergencies on short notice.
Job description and application forms available at www.cheshire-ma.gov. Applications and Résumés will be accepted until the position is filled. Mail responses to Town of Cheshire, Town Administrator, 191 Church Street, Cheshire, MA 01225, or email [email protected] . AA/EOE.
Posted: 10/7/26
Volunteer Opportunities
Do you have a few hours to offer to our community? A list of volunteer opportunities is listed below. Please submit a Volunteer Interest Form to the Town Administrator. Appointments will be made by the Board of Selectmen to these positions.
- Keeper of the Pound
- Fence Viewer (3 Positions)
- Northern Berkshire Cable Representative
- Council on Aging Alternate
- Historical Commission member and alternate
- Finance Committee Member (1)
- Board of Health Member (1) to fill the term expiring in May 2027 (elected position)
Updated: 7/22/26