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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.

April 30, 2026
Event Date2026-04-30T16:00:00 - 2026-04-30T18:00:00

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

April 30, 2026
Event Date2026-04-30T16:00:00 - 2026-04-30T18:00:00

2026 Children's Arts and Crafts Workshops: Brighton

Looking for a free, fun activity to enjoy with the kids? Join us this summer for one of our arts and crafts workshops hosted in various parks throughout the City of Boston, hosted by a local artist.

July 24, 2026
  • 10:00am - 12:00pm
    Repeats weekly on Friday, starting from July 10, 2026, until July 24, 2026
  • Joyce Playground
    80 Union Street
    BOSTON , MA 02135
  • Contact:
    PARKS AND RECREATION
  • Price:
    Price
    FREE
  • Neighborhood:
    Neighborhood
    Brighton
  • Event Type:
  • Published Date
Event Date2026-07-24T10:00:00 - 2026-07-24T12:00:00

Our arts and crafts workshops are led by local artists. They're held Tuesday through Friday in July and August and run from 10 a.m. until 12 p.m. These drop-in workshops encourage kids to explore their creativity through projects like mask making, crayon art, watercolor and much more. Supplies are provided, but you'll need to bring your creativity! 

This series is completely free and open to Boston residents. These workshops will take place in various parks throughout the City of Boston.

Registration is required for groups of 8 or more. Please email allison.singer2@boston.gov to register.

This series is weather-dependent. Check our social media pages for updated weather info regarding this series. Follow us on social media for the latest updates on events: Facebook, Instagram and Bluesky.

July 24, 2026
  • 10:00am - 12:00pm
    Repeats weekly on Friday, starting from July 10, 2026, until July 24, 2026
  • Joyce Playground
    80 Union Street
    BOSTON , MA 02135
  • Contact:
    PARKS AND RECREATION
  • Price:
    Price
    FREE
  • Neighborhood:
    Neighborhood
    Brighton
  • Event Type:
  • Published Date
Event Date2026-07-24T10:00:00 - 2026-07-24T12:00:00

2026 Children's Arts and Crafts Workshops: Jamaica Plain

Looking for a free, fun activity to enjoy with the kids? Join us this summer for one of our arts and crafts workshops hosted in various parks throughout the City of Boston, hosted by a local artist.

July 24, 2026
  • 10:00am - 12:00pm
    Repeats weekly on Friday, starting from July 10, 2026, until July 24, 2026
  • Mozart Street Playground
    50 Mozart Street
    BOSTON , MA 02130
  • Contact:
    PARKS AND RECREATION
  • Price:
    Price
    FREE
  • Neighborhood:
    Neighborhood
    Jamaica Plain
  • Event Type:
  • Published Date
Event Date2026-07-24T10:00:00 - 2026-07-24T12:00:00

Our arts and crafts workshops are led by local artists. They're held Tuesday through Friday in July and August and run from 10 a.m. until 12 p.m. These drop-in workshops encourage kids to explore their creativity through projects like mask making, crayon art, watercolor and much more. Supplies are provided, but you'll need to bring your creativity! 

This series is completely free and open to Boston residents. These workshops will take place in various parks throughout the City of Boston.

Registration is required for groups of 8 or more. Please email allison.singer2@boston.gov to register.

This series is weather-dependent. Check our social media pages for updated weather info regarding this series. Follow us on social media for the latest updates on events: Facebook, Instagram and Bluesky.

July 24, 2026
  • 10:00am - 12:00pm
    Repeats weekly on Friday, starting from July 10, 2026, until July 24, 2026
  • Mozart Street Playground
    50 Mozart Street
    BOSTON , MA 02130
  • Contact:
    PARKS AND RECREATION
  • Price:
    Price
    FREE
  • Neighborhood:
    Neighborhood
    Jamaica Plain
  • Event Type:
  • Published Date
Event Date2026-07-24T10:00:00 - 2026-07-24T12:00:00

ADU Budget Workshop

Are you planning to build an Additional Dwelling Unit (ADU) and have questions about the anticipated costs? Sign up for a virtual budget workshop!

March 4, 2026
  • 4:30pm - 6:00pm
    Repeats monthly on Wednesday, but only the first instance of this set, starting from March 4, 2026, until March 4, 2028
  • Contact:
    Mayor's Office of Housing
  • Price:
    Price
    FREE
  • Event Type:
  • Published Date
Event Date2026-03-04T16:30:00 - 2028-03-04T18:00:00

The Accessory Dwelling Unit (ADU) Budget Workshop is an opportunity for Boston homeowners who are interested in building an ADU in their home or on their property to develop a plan to budget for and finance their project.

The workshop is open to the public. Participation in the ADU Budget Workshop and ADU Design Workshop is required to qualify for the Boston Home Center's ADU Financial Assistance Program. 

The workshop is a helpful step in making a financial plan and determining the cost and financial feasibility of building an ADU on your property.

March 4, 2026
  • 4:30pm - 6:00pm
    Repeats monthly on Wednesday, but only the first instance of this set, starting from March 4, 2026, until March 4, 2028
  • Contact:
    Mayor's Office of Housing
  • Price:
    Price
    FREE
  • Event Type:
  • Published Date
Event Date2026-03-04T16:30:00 - 2028-03-04T18:00:00

Free Smoke/ Carbon Monoxide Detectors Installation

For residents of Hyde Park and Mattapan.

April 25, 2026
Event Date2026-04-25T09:00:00 - 2026-04-25T16:00:00

The Boston Fire Department, in collaboration with the American Red Cross, is offering free home installation for 10-year battery-powered smoke/carbon monoxide detectors. The installation will be for Hyde Park and Mattapan residents.

Sign up today

Priority Installations are for owner-occupied homes of vulnerable or low-income populations. Future events will be announced at a later date.

This initiative is funded by the U.S. Consumer Product Safety Commission (CPSC) through a grant award to the Boston Fire Department. 75% of the project cost is federally funded ($260.031.75)

Flyer

April 25, 2026
Event Date2026-04-25T09:00:00 - 2026-04-25T16:00:00

Free Bike Repair Workshop at BPL South Boston

Join us for a free, hands-on workshop!

August 11, 2026
  • 3:30pm - 5:30pm
    Repeats monthly on Tuesday, but only the second instance of this set, starting from March 10, 2026, until October 13, 2026
  • 646 E BROADWAY BOSTON
    Boston, MA 02127
  • Contact:
    Boston Bikes
  • Price:
    Price
    FREE
  • Neighborhood:
    Neighborhood
    South Boston
  • Event Type:
  • Published Date
Event Date2026-08-11T15:30:11 - 2026-08-11T17:30:11

We do all basic bike repair including: patch tires, align brakes, and adjust gears and shifters.

These events take place monthly on a Tuesday from 3:30 - 5:30 p.m.  No registration required. The event is first come, first serve.

August 11, 2026
  • 3:30pm - 5:30pm
    Repeats monthly on Tuesday, but only the second instance of this set, starting from March 10, 2026, until October 13, 2026
  • 646 E BROADWAY BOSTON
    Boston, MA 02127
  • Contact:
    Boston Bikes
  • Price:
    Price
    FREE
  • Neighborhood:
    Neighborhood
    South Boston
  • Event Type:
  • Published Date
Event Date2026-08-11T15:30:11 - 2026-08-11T17:30:11

Library Essentials

Partnering with the Boston Public Library to explore resources available through the BPL for Returning Citizens. 

December 17, 2025
  • 1:30pm - 2:30pm
    Repeats monthly on Wednesday, but only the third instance of this set, starting from September 24, 2025, 20 times
  • 30 Dimock Street
    Roxbury, MA 02119
  • Contact:
    Rechelle Hypolite
  • Price:
    Price
    FREE
  • Neighborhood:
    Neighborhood
    Roxbury
  • Event Type:
  • Published Date
Event Date2025-12-17T13:30:39 - 2026-07-22T14:30:39

Join us to learn more about FREE BPL resources, including a library card, free printing, digital access skills, and discuss library programs and services that are available to all, including:

• business, career, and job search programs and services

• programs for families, children, and teens

• museum passes, concerts, and author talks

• technology available at the library

• online resources including ebooks and audiobooks, databases, & streaming films and much more

Library essential evergreen

December 17, 2025
  • 1:30pm - 2:30pm
    Repeats monthly on Wednesday, but only the third instance of this set, starting from September 24, 2025, 20 times
  • 30 Dimock Street
    Roxbury, MA 02119
  • Contact:
    Rechelle Hypolite
  • Price:
    Price
    FREE
  • Neighborhood:
    Neighborhood
    Roxbury
  • Event Type:
  • Published Date
Event Date2025-12-17T13:30:39 - 2026-07-22T14:30:39

Immigrant Advancement Community Office Hours - Copley

Join us for our in-person Community Office Hours! 

July 23, 2026
  • 12:30pm - 2:30pm
    Repeats monthly on Thursday, but only the 4th instance of this set, starting from February 26, 2026, until December 24, 2026
  • 700 Boylston St.
    Boston, MA 02116
  • Contact:
    Mayor's Office for Immigrant Advancement
  • Price:
    Price
    FREE
  • Neighborhood:
    Neighborhood
    Back Bay
  • Published Date
Event Date2026-07-23T12:30:00 - 2026-07-23T14:30:00

Looking for support getting connected to resources and navigating City services? Meet with the Mayor’s Office for Immigrant Advancement during our community office hours at the Copley Branch of the Boston Public Library. 

Office hours will take place on the following days:

  • First Thursday of every month from 4 - 7 p.m. at the East Boston branch
  • Fourth Thursday of every month from 12:30 p.m. - 2:30 p.m. at the Copley branch

Registration is not required, and interpretation and disability accommodations will be available.

Community office hours flyer

July 23, 2026
  • 12:30pm - 2:30pm
    Repeats monthly on Thursday, but only the 4th instance of this set, starting from February 26, 2026, until December 24, 2026
  • 700 Boylston St.
    Boston, MA 02116
  • Contact:
    Mayor's Office for Immigrant Advancement
  • Price:
    Price
    FREE
  • Neighborhood:
    Neighborhood
    Back Bay
  • Published Date
Event Date2026-07-23T12:30:00 - 2026-07-23T14:30:00

Age Strong Memory Cafe - Jamaica Plain

A Memory Café is a welcoming place for people with forgetfulness or other changes in their thinking.

 

July 27, 2026
  • 10:30am - 12:00pm
    Repeats monthly on Monday, but only the last instance of this set, starting from June 30, 2025, until December 31, 2026
  • Boston Public Library - Jamaica Plain Branch
    30 South Street
    Jamaica Plain, MA 02130
  • Contact:
    Corinne White
  • Price:
    Price
    FREE
  • Neighborhood:
    Neighborhood
    Jamaica Plain
  • Event Type:
  • Published Date
Event Date2026-07-27T10:30:00 - 2026-07-27T12:00:00

A flyer detailing Age Strong's Jamaica Plain Memory Cafe, hosted at the Jamaica Plain Branch of the Boston Public Library

Memory cafés meet at a variety of places, including coffeehouses, museums, or community organizations. Each memory café is different. Some cafés invite guest artists, some offer education about memory changes. And some are just for relaxing and chatting. But, all cafés share one goal — to help guests feel comfortable and to know that they are not alone. Cafés are a place to talk with others who understand what you are going through. You can forget about your limitations and instead focus on your strengths.

*Bilingual in Spanish*

Jamaica plain BRANCH OF THE BOSTON PUBLIC LIBRARY

30 South Street, Jamaica Plain

Meets the last Monday of every month, from 10:30 a.m. - 12 p.m.

For information, contact: Corinne White at 617-635-3745 | corinne.white@boston.gov

Download the flyers below:

English

Spanish

 

 

July 27, 2026
  • 10:30am - 12:00pm
    Repeats monthly on Monday, but only the last instance of this set, starting from June 30, 2025, until December 31, 2026
  • Boston Public Library - Jamaica Plain Branch
    30 South Street
    Jamaica Plain, MA 02130
  • Contact:
    Corinne White
  • Price:
    Price
    FREE
  • Neighborhood:
    Neighborhood
    Jamaica Plain
  • Event Type:
  • Published Date
Event Date2026-07-27T10:30:00 - 2026-07-27T12:00:00

Age Strong Support Group for Dementia Care Partners

Join our support group to connect with others & share experiences. Gain helpful information & resources.

April 25, 2025
  • 12:00pm - 1:00pm
    Repeats monthly on Friday, but only the 4th instance of this set, starting from April 25, 2025, until April 24, 2026
  • Boston Centers for Youth and Families (BCYF) Roslindale
    6 Cummins Highway
    Roslindale, MA 02131
  • Contact:
    Corinne White
  • Price:
    Price
    FREE
  • Neighborhood:
    Neighborhood
    Roslindale
  • Event Type:
  • Published Date
Event Date2025-04-25T12:00:00 - 2025-04-25T13:00:00

A flyer for Age Strong's Support Group for Dementia Care Partners. On the bottom of the fly is a picture of an older adult man and a woman with text above them that reads "You are not alone"

Boston Centers for Youth & Families (BCYF) Roslindale

6 Cummins Highway, Roslindale

Meets on the 4th Friday each month, from 12 pm -1 pm.

For information, contact: Corinne White at 617-635-3745 | corinne.white@boston.gov

View & download flyer here

April 25, 2025
  • 12:00pm - 1:00pm
    Repeats monthly on Friday, but only the 4th instance of this set, starting from April 25, 2025, until April 24, 2026
  • Boston Centers for Youth and Families (BCYF) Roslindale
    6 Cummins Highway
    Roslindale, MA 02131
  • Contact:
    Corinne White
  • Price:
    Price
    FREE
  • Neighborhood:
    Neighborhood
    Roslindale
  • Event Type:
  • Published Date
Event Date2025-04-25T12:00:00 - 2025-04-25T13:00:00
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