Retiree Benefits

Beginning July 1, 2015, the City of Pittsfield will be switching their health insurance coverage to Blue Cross Blue Shield of Massachusetts through the Massachusetts Interlocal Association .  Due to this change, all current subscribers and new enrollees to the City’s health plan must sign up for new insurance plan during the open enrollment period.  The open enrollment is now through the first week of May for non-Medicare retirees. Information regarding the new Blue Cross Blue Shield plans are available via

Retirees of the City of Pittsfield and the Pittsfield Public School Department are eligible to continue their health insurance coverage through the City.  If you retire before age 65, you are eligible for the same plans as the City's active employees provided you are not Medicare eligible due to disability.  Please refer to the Employee Benefits section for more information.  

If you or your spouse are on one of the plans above and you or your spouse turn age 65, you will be required to provide evidence of Medicare eligibility.  If you are eligible for Medicare, it becomes your primary coverage and the City offers the Blue Cross Medex supplemental plan.  This plan is to supplement costs in which Medicare does not pay in full.  A Summary of Benefits for the Blue Cross Medex Medicare supplemental plan is available via or from the City Treasurer's office.

Retiree Dental Insurance

Dental insurance for retirees of the City of Pittsfield and the Pittsfield Public School Department is also available through Blue Cross Blue Shield of Massachusetts.

To enroll, you may do so either upon retirement or during an open enrollment. Open enrollment for non-Medicare retiree’s is typically the first week of April through the first week of May and coverage beings annually on July 1st. Open enrollment for Medicare eligible retirees is typically in October and coverage is effective January 1st.

Please note:
The supplemental plans offered by the City fulfill the 'Creditable Coverage' requirements for Medicare Part D (prescription coverage).