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Employment Opportunities

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

DPW Highway Heavy Equipment Operator

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.

  • Community House Building Design Committee -  Work will be limited to selection of a vendor/designer to conduct an assessment/feasbility of the oldest sections of the Community House (former elementary school)
  • Fence Viewer -  Administers fence laws by inspecting new fences and settles disputes arising from trespass by livestock that escaped enclosure.  
  • Council on Aging Alternate - Serves in the absense of Council on Aging members.  Council on Aging members coordinate and carry out program designed to met the needs of the aging.
  • Historical Commission member and alternate-  Preservation of town history
  • Finance Committee Member (1)-  Consider all appropriations recommended by the Board of Selectmen for the financial year, also the articles in the warrant calling for funds and make recommendations.   
  • Board of Health Member (1) to fill the term expiring in May 2027 (elected position)

Updated: 10/23/26