Frequently Asked Questions and Answers

How can I request a suitability letter?

Requests may be sent to

As a new benefit eligible employee (20 hours or more per week), when must I enroll for Health Insurance?  

Employees must enroll in health insurance within 30 days from their date of hire.

When does annual enrollment for health insurance take place?

Open enrollment begins April 3rd and ends May 11th for a July 1st start date.

Who do I call about questions regarding changing my primary care physician or my insurance ID cards?

Subscribers must contact either Blue Cross Blue Shield or Harvard Pilgrim to change their Primary Care Physician (PCP). To order I.D. cards, call Member Service at: (BCBS) 800-782-3675, (HP) 888-333-4742. 

Can retirees of the Town participate in the Town's health insurance plans?  

Retired employees receiving a pension from the town are eligible to participate in the Town's health insurance plans if they were eligible to receive benefits prior to their retirement.  

Who can be an eligible dependent on my health insurance? 

Legally Married Spouse, and dependents up to age 26, or a disabled dependent.

What Constitutes a Qualifying Event for a Special Health Insurance Enrollment?

Involuntary loss of coverage under another health plan (Spouse/Parent), Marriage, birth of a child, adoption of a child.   

What happens with my health insurance coverage when I turn 65?

Anyone turning 65 must enroll in Medicare through the Social Security Administration. Retirees have the option of purchasing Medicare supplemental health insurance through the Town.

For additional questions please contact the Payroll/Benefits Office at 781-878-0786 or email