General Information

Cheshire, Massachusetts

Cheshire is one of several smaller Berkshire County communities in Western Massachusetts that is seeing its population grow! Come and visit and you will see why! Walk the Ashuwillticook Rail Trail; take a boat out on our beautiful lake and hike the Appalachian Trail which crosses through the center of our town! These and so much more are what makes the town of Cheshire so special!

FY 2019 Cheshire Budget [PDF]                 ATM Warrant FY 2019 [PDF]

The Ashuwillticook Rail Trail

The Ashuwillticook Rail Trail is a former railroad corridor converted into a 10-foot (3.0 m) wide paved universally accessible scenic rail trail path. The Ashuwillticook (ash-oo-will-ti-cook) Rail Trail runs parallel to Route 8 through the towns of Cheshire, Lanesborough and Adams, Massachusetts and has become a popular resource for biking, walking, rollerblading, and jogging. The trail is managed by the Massachusetts Department of Conservation and Recreation (DCR). .... more





Appalachian Trail Community™


November 6, 2018 Election Results [PDF]





Town of Cheshire

Town Administrator Duties and Responsibilities

Position Title: Town Administrator

Statement of Duties

Professional administrative, technical and supervisory work in managing and directing town activities, departments and projects on behalf of the Board of Selectmen including the establishment of departmental goals and objectives, policies and regulations. Researches, analyzes and recommends improvements in town policies, personnel, systems and procedures, and serves as liaison and coordinator between town officials, employees and citizens; all other related work as required.

Current Work Hours, Salary and Employment Agreement

This is a newly expanded position. Although specific work days and work schedule would be negotiated with the Board of Selectmen, this position requires a minimum of 24 hours per week spent in the Town Hall and environs. Town meeting has appropriated an annual salary of $40,000 (FY 2019) for this position. An employment agreement shall be executed with the Board of Selectmen which may have a probationary one-year employment clause and shall not exceed three years in length.


Works under the direction of the Board of Selectmen. The Board of Selectmen are the Chief Elected Officials whereas the Town Administrator shall act as the Chief Executive Officer. The Town Administrator functions with considerable independence and is directly accountable for actions.

Performs highly responsible work of a complex nature requiring the exercise of considerable independent judgment and initiative in providing professional guidance to the Board of Selectmen, department heads, town departments, boards and committees, concerning the development, implementation and administration of policies, goals, regulations, and statutory requirements related to the administration and operation of the Town. Position involves analyzing difficult administrative problems and recommending solutions.

Employee has direct supervisory responsibility for all department heads reporting to the Board of Selectmen, clerical staff, and several part-time positions. Responsible for coordinating the work and administrative activities of those employees not reporting directly to the Board of Selectmen.  Evaluates department heads; recommends disciplinary actions to Board of Selectmen. Recruits, screens and recommends personnel to Board of Selectmen for appointment.  However, the Board of Selectmen has sole hiring and employee dismissal authority. Employees are located at different locations.

Job Environment

Work is performed under typical office conditions. Position requires attendance at weekly Board of Selectmen meetings, other occasional night meetings. Town Administrator may be contacted at home at any time to respond to important situations and emergencies. Incumbent may be required to attend social and civic events to represent the Town.

Prepares and administers the operating and capital budgets of the Town. Prepares, administers and presents the Annual and Special Town Meeting warrants.

Operates a computer and associated technical software, and general office equipment such as a calculator, e-mail, facsimile, and telephone.

Employee makes constant and direct contact with the public requiring significant perceptiveness and discretion with all departments and boards, members of the business and civic community, labor union representatives, attorneys, and state, federal and local officials as well as the media.  Contacts require excellent customer services skills, persuasiveness, and resourcefulness to influence the behavior of others.

Employee has access to an extensive variety of confidential information, including lawsuits and settlements, criminal investigations, bid proposals, negotiating strategies, personnel records. Position requires the use of extensive judgment and initiative within policies and procedures that may require interpretation and direction to others and developing appropriate responses.

Errors in judgment could have a significant and continuous effect on the town’s ability to deliver services and may have direct financial and legal repercussions, loss of revenue, damage to buildings or equipment, injury to employees, and cause considerable adverse public relations.  Responsible for the safety of all town employees and building operations.

Essential Functions

The essential functions or duties listed below are intended only as illustrations of the various types of work that may be performed.  The omission of specific statements of duties does not exclude them from the position if the work is similar, related, or a logical assignment to the position.

Oversees and responsible for the planning, administration, personnel management, union negotiations, procurement of services/equipment (shall have the designation of Chief Procurement Officer), and coordination of the daily operation of the Town as delegated by the Board of Selectmen and the requirements of existing policies, procedures and bylaws, state statutes and federal laws.  

Provides leadership and direction in the development of short and long-range plans; gathers, interprets and prepares data for studies, reports and recommendations. Provides professional advice to Selectmen and department heads, makes presentations to boards, town meeting and the general public.  

Acts as Chief Administrative Officer for the Board of Selectmen; prepares the agenda, attends all meetings of the Board.  Receives and makes appropriate disposition or referral of all Board correspondence and communications.  Anticipates needs of the Selectmen for information and background material. Ensures that all decisions of the Board are carried out. Keeps the Board fully advised regarding departmental operations and financial health.

Establishes goals, objectives, policies based on the needs of the Town. Provides supervision, direction and guidance including regular communication and development of goals/objectives for all town staff and reporting department heads; assists all department in any administrative or operational areas to insure regulatory, statutory or procedural compliance.

Establishes and oversees budget process from developing instructions and setting deadlines, to providing materials and recommendations for Finance Committee reviews. Coordinates the development of strategic financial goals for the Town. Makes recommendations concerning financial policies and practices.  Reviews all revenues collected and make recommendations concerning fees, charges, and Enterprise Fund rates as well as new sources of revenue.  

Conducts all collective bargaining and negotiation of employment contracts.  Develops and recommends bargaining concepts and strategies for Board’s approval.  Attends all bargaining sessions and/or grievance hearings. Advise officials on impact of contract terms on personnel system, wage administration.

Consults with department heads and employees of every rank on sensitive issues involving performance problems, health issues, management styles, contract interpretation, leave and attendance, job assignments.

Serves as the Board of Selectmen’s liaison and representative to town boards, committees, local state and federal agencies. Negotiates with citizens and other outside public and private agencies; assists citizens in their interaction with all town departments, boards and committees in the delivery of town services. Responds to oral and written inquires, requests for assistance, and complaints; refers citizens to appropriate departments and staff member. Investigates complaints from a variety of sources; develops responses and, when appropriate, directs corrective action.

Prepares and writes all town meeting warrants and motions.  Develops, writes and compiles background materials for town meeting.  Directs all mailings and insures the development of quality products.

Oversees all Town automated management information systems, makes recommendations for improvements and implements appropriate policies relative to systems.

Oversees coordination and compilation of annual town reports, annual licenses and appointments.

Prepares applications for grants, administers grants received, works with appropriate state and private officials on projects.

Oversees all town building maintenance, construction and repairs.

Works on special projects; performs similar or related work as required or a situation dictates.

Recommended Minimum Qualifications

Education and Experience

Minimum of Bachelor's Degree in finance, public/business administration or related field preferred although demonstration of relevant prior work history may be considered in the absence of preferred education; minimum of five- (5) years of municipal management experience as a Chief Administrative Officer, or a related field; municipal management strongly preferred; or any equivalent combination of education and experience. Experience with Massachusetts's general laws, collective bargaining, personnel administration, and town meeting process.

Knowledge, Ability and Skill

Knowledge:   Knowledge of Massachusetts General Laws (Chapter 30B, 32B), and federal statutes (FLSA, FMLA, AA/EEO/ADA etc), pertaining to municipal government including finance, budget, personnel policies and practices, collective bargaining, systems management and operations. Expertise in the operation and organization of municipal government.  Sufficient knowledge of emerging technologies and to recognize its value to the Town.  Comprehensive knowledge of the various financial requirements of municipal government.  Proficiency in various computer software and hardware applications.

Ability: Ability to direct and evaluate the work of department heads as well as professionals and other subordinates including office staff.  Ability to plan, organize, and direct the development of projects, the preparation of reports, analyzes problems and formulates recommendations. Ability to bring people together around complex goals and develop consensus among community groups and individuals that may not share common priorities. Ability to establish and maintain harmonious and effective working relationships and deal appropriately with employees, board/committee members, agencies and officials, media and the public. Ability to prioritize and manage multiple tasks, and delegate authority in a prompt and effective manner. Ability to negotiate contracts, agreements and appropriate working arrangements and achieve timely results under stressful circumstances.

Skill:  Strong oral communication skills and the ability to represent the Town before an array of organizations including providing statements to the media.  Excellent writing skills required to prepare various reports and position papers.  Strong organizational skills and the ability to manage a large number or projects and tasks. Skill in the utilization of technology as a means of strengthening the organization and its services.  Professional skills related to customer service.  Skill in remaining non-political, yet understanding local government politics.

Physical Requirements

Minimal physical effort generally required in performing duties under typical office conditions.  Position requires the ability to operate and view a keyboard and standard office equipment.  The employee is frequently required to use hands to finger, handle, or feel objects, tools or controls and reach with hands and arms.  The employee is frequently required to sit, talk and hear.  Incumbent may be required to lift up to 10 pounds. Equipment operated includes automobile, office machines, pager and computer.