Chief of Police - Cheshire, MA

The Town of Cheshire, Massachusetts is seeking a highly qualified and experienced law enforcement professional to serve as its next Police Chief. This leadership role offers the opportunity to deliver effective, community-oriented public safety services while fostering trust, accountability, and strong relationships with residents. The selected candidate will have the unique opportunity to serve as a working Police Chief, working hand in hand with community members and department personnel to address local needs in a visible, hands-on leadership capacity. The ideal candidate will bring proven supervisory experience, sound judgment, and a collaborative leadership style, along with a commitment to upholding the highest standards of integrity and professionalism in policing.

COMMUNITY

Located in Berkshire County, Massachusetts, Cheshire is a close-knit community known for its rich history, scenic beauty, and strong civic spirit. Famous for the historic “Mammoth Cheese” presented to President Thomas Jefferson, Cheshire today is recognized for its rural character, welcoming neighborhoods, and exceptional outdoor resources, including the Appalachian Trail, Cheshire Reservoir, and Ashuwillticook Rail Trail. Residents value the town’s tradition of community involvement, public safety, and quality of life, making Cheshire an attractive place to live, work, and serve.

Cheshire is a town that values its past while investing in a safe and vibrant future. It’s an ideal setting for leaders who value tradition, service, and authentic community connection.

THE DEPARTMENT 

The Cheshire Police Department is dedicated to delivering both traditional and non-traditional law enforcement services to residents and visitors alike. The Department operates with a strong emphasis on compassion, integrity, and ethical conduct, ensuring that every interaction reflects the values of the community it serves.

The Cheshire Police Department is a full-service agency consisting of two full time patrol officers with planned growth for one additional officer, dependent on upcoming town meeting. The Police Chief will also oversee a shared animal control officer.   

RECOMMENDED QUALIFICATIONS

• Bachelor’s Degree in Law Enforcement, Criminal Justice or related field. Familiarity and experience with community-oriented policing process; or an equivalent combination of education and experience. Graduates of major policing executive development programs including FBI National Academy, Police Executive Research Forum Senior Management Institute for Police or Police Executive Leadership Institute, and FBI LEEDA are encouraged to apply.
• Experience: A minimum of ten (10) years’ experience in law enforcement, with at least three (3) years in a significant command or supervisory capacity.
• Candidates must be active in the Law Enforcement field and hold a minimum rank of sergeant to apply. Any equivalent combination of education and experience may also be considered. 
• Possession of or ability to obtain a valid Massachusetts driver’s license. 
• Must have a valid Massachusetts Firearms License or the ability to obtain one upon hire.
• Applicants must graduate from the Commonwealth of Massachusetts Municipal Police Training Committee (MPTC) Basic Recruit Officer Academy (or eligible for a Permanent Exemption by the MPTC). They must satisfy all requirements set forth by the Massachusetts Peace Officer Standards and Training Commission for certification as a Police Officer in the Commonwealth of Massachusetts.

Interested applicants should email a cover letter and résumé as a single PDF file to Public Safety Consultants, LLC at rstevenspublicsafetyllc@gmail.com. Cover letters and resumes should be received by 10:00 A.M. on Thursday, June 11^th, 2026.