Annual Enrollment 2026 Benefits Fair
City of Boston employees and retirees can get in-person support with Annual Enrollment questions, forms, and health plan changes.
The City of Boston’s 2026 Annual Enrollment period runs from April 27 through May 15. During this time, City employees and retirees can enroll in, change, or cancel health insurance coverage without a qualifying life event.
Need help with Annual Enrollment? Visit a Benefits Fair to ask questions, review your health insurance options, and get support with forms, deadlines, and enrollment changes. See the schedule of events below for details:
| DATE | TIME | LOCATION |
|
Thursday, April 30 |
4:00 p.m. - 6:00 p.m. |
Boston Teachers Union, 180 Mt. Vernon Street, Dorchester, MA 02125 |
|
Tuesday, May 5 |
11:00 a.m. - 2:00 p.m. |
Florian Hall, 55 Hallet St, Dorchester, MA 02122 |
|
Wednesday, May 13 |
10:00 a.m. - 2:00 p.m. |
Boston City Hall, Room 801 |
📌This event is intended for City of Boston employees and retirees only.
For plan information, forms, and Annual Enrollment details, visit boston.gov/enroll