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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.

May 13, 2026
Event Date2026-05-13T10:00:00 - 2026-05-13T14:00:00

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

May 13, 2026
Event Date2026-05-13T10:00:00 - 2026-05-13T14:00:00

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.

May 5, 2026
Event Date2026-05-05T11:00:00 - 2026-05-05T14:00:00

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

May 5, 2026
Event Date2026-05-05T11:00:00 - 2026-05-05T14:00:00

Learn-to-Bike for Adults: Road Readiness

Gain on-bike confidence skills! We will learn & practice hand signals and advanced bike handling. Class open to all genders.

June 6, 2026
  • 10:00am - 12:00pm
  • Mattahunt School Parking Lot
    100 Hebron Street
    Boston, MA 02126
  • Contact:
    Boston Bikes
  • Price:
    Price
    FREE
  • Neighborhood:
    Neighborhood
    Mattapan
  • Published Date
Event Date2026-06-06T10:00:41 - 2026-06-06T12:00:41

Bicycle Road Readiness Skills (Level 3)

two side-by-side photos showing captures from Level 3 on-bike workshop for adults

If you have the basic biking skills like starting, stopping, and turning, but want to build your confidence to ride in the street, come to a free Road Readiness clinic for adults. Our experienced staff and volunteers will help each participant gain skills and confidence so you’re ready to venture onto the street and keep on rolling! This class is taught entirely in a parking lot. We will run through some fun activities to build skills like using hand signals, shifting gears, and riding in a steady line. You’ll get lots of practice and one-on-one support. This class is open to people of all genders, bikes and helmets provided for duration of the workshop, registration required.

 

If you cannot yet ride independently across a parking lot, please do not register for this clinic. Our Basic Skills class is more appropriate.

 

June 6, 2026
  • 10:00am - 12:00pm
  • Mattahunt School Parking Lot
    100 Hebron Street
    Boston, MA 02126
  • Contact:
    Boston Bikes
  • Price:
    Price
    FREE
  • Neighborhood:
    Neighborhood
    Mattapan
  • Published Date
Event Date2026-06-06T10:00:41 - 2026-06-06T12:00:41

Stepping Strong Center: Virtual Stop the Bleed Training

April 15, 2026
  • 12:00pm - 6:00pm
  • Zoom
    Boston,
  • Contact:
    Stepping Strong Center
  • Price:
    Price
    FREE
  • Neighborhood:
    Neighborhood
    Citywide
  • Event Type:
  • Published Date
Event Date2026-04-15T12:00:00 - 2026-04-15T18:00:00

Join the Stepping Strong Center on Wednesday, April 15, for free Zoom sessions at 12:00 p.m. or 6:00 p.m. to learn how to recognize life-threatening bleeding and take immediate, effective action. Registration:

12 p.m. session

6 p.m. Session

April 15, 2026
  • 12:00pm - 6:00pm
  • Zoom
    Boston,
  • Contact:
    Stepping Strong Center
  • Price:
    Price
    FREE
  • Neighborhood:
    Neighborhood
    Citywide
  • Event Type:
  • Published Date
Event Date2026-04-15T12:00:00 - 2026-04-15T18:00:00

Kush Grove Soft Opening

Kush Grove is open for business! 

April 10, 2026
  • 11:00am - 8:00pm
  • 1589 Columbus Avenue
    Roxbury, MA 02119
  • Contact:
    Akilah Armstrong
  • Price:
    Price
    Prices may vary
  • Neighborhood:
    Neighborhood
    Roxbury
  • Event Type:
  • Published Date
Event Date2026-04-10T11:00:00 - 2026-04-10T20:00:00

Come support the Kush Grove team on their first day of business! Check out their Boston Cannabis Board Presentation video below.

BCB Presentation

February 10, 2021 Transactional Hearing

April 10, 2026
  • 11:00am - 8:00pm
  • 1589 Columbus Avenue
    Roxbury, MA 02119
  • Contact:
    Akilah Armstrong
  • Price:
    Price
    Prices may vary
  • Neighborhood:
    Neighborhood
    Roxbury
  • Event Type:
  • Published Date
Event Date2026-04-10T11:00:00 - 2026-04-10T20:00:00

Lowkey Dispensary Grand Opening Celebration

Come celebrate the opening of Lowkey Dispensary in West Roxbury!

April 18, 2026
  • 3:00pm - 8:00pm
  • Lowkey Dispensary
    5268 Washington Street
    Boston, MA 02132
  • Contact:
    Akilah Armstrong
  • Price:
    Price
    FREE
  • Neighborhood:
    Neighborhood
    West Roxbury
  • Event Type:
  • Published Date
Event Date2026-04-18T15:00:00 - 2026-04-18T20:00:00

Join the Cannabis Industry Development Team in celebrating the grand opening of Lowkey Dispensary! Enjoy vendor activations, giveaways, music and more! 

Citation of Recognition presentation at 5:00 p.m. 

flyer

April 18, 2026
  • 3:00pm - 8:00pm
  • Lowkey Dispensary
    5268 Washington Street
    Boston, MA 02132
  • Contact:
    Akilah Armstrong
  • Price:
    Price
    FREE
  • Neighborhood:
    Neighborhood
    West Roxbury
  • Event Type:
  • Published Date
Event Date2026-04-18T15:00:00 - 2026-04-18T20:00:00

Age Strong Rotating Memory Cafe - North End

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

September 11, 2026
  • 11:30am - 1:00pm
  • North End Branch of the Boston Public Library
    25 Parmenter Street, North End
    Boston, MA 02113
  • Contact:
    Corinne Brindley
  • Price:
    Price
    FREE
  • Neighborhood:
    Neighborhood
    North End
  • Event Type:
  • Published Date
  • Downloads:
Event Date2026-09-11T11:30:00 - 2026-09-11T13:00:00

Age Strong Rotating Memory Cafes - North End 2026

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.

North End Branch of the Boston Public Library

365 Bremen Street, East Boston

For information, contact: Corinne Brindley at 617-635-3745, corinne.brindley@boston.gov

September 11, 2026
  • 11:30am - 1:00pm
  • North End Branch of the Boston Public Library
    25 Parmenter Street, North End
    Boston, MA 02113
  • Contact:
    Corinne Brindley
  • Price:
    Price
    FREE
  • Neighborhood:
    Neighborhood
    North End
  • Event Type:
  • Published Date
  • Downloads:
Event Date2026-09-11T11:30:00 - 2026-09-11T13:00:00

Age Strong Rotating Memory Cafe - North End

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

July 31, 2026
  • 11:30am - 1:00pm
  • North End Branch of the Boston Public Library
    25 Parmenter Street, North End
    Boston, MA 02113
  • Contact:
    Corinne Brindley
  • Price:
    Price
    FREE
  • Neighborhood:
    Neighborhood
    North End
  • Event Type:
  • Published Date
  • Downloads:
Event Date2026-07-31T11:30:00 - 2026-07-31T13:00:00

Age Strong Rotating Memory Cafes - North End 2026

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.

North End Branch of the Boston Public Library

365 Bremen Street, East Boston

For information, contact: Corinne Brindley at 617-635-3745corinne.brindley@boston.gov

July 31, 2026
  • 11:30am - 1:00pm
  • North End Branch of the Boston Public Library
    25 Parmenter Street, North End
    Boston, MA 02113
  • Contact:
    Corinne Brindley
  • Price:
    Price
    FREE
  • Neighborhood:
    Neighborhood
    North End
  • Event Type:
  • Published Date
  • Downloads:
Event Date2026-07-31T11:30:00 - 2026-07-31T13:00:00

Age Strong Rotating Memory Cafe - East Boston

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

October 9, 2026
Event Date2026-10-09T11:30:00 - 2026-10-09T13:00:00

Age Strong Rotating Memory Cafes - East Boston 2026

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.

 

East Boston Branch of the Boston Public Library

365 Bremen Street, East Boston

 

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

October 9, 2026
Event Date2026-10-09T11:30:00 - 2026-10-09T13:00:00

Age Strong Rotating Memory Cafe - East Boston

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

June 12, 2026
Event Date2026-06-12T11:30:00 - 2026-06-12T13:00:00

Age Strong Rotating Memory Cafes - East Boston 2026

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.

 

East Boston Branch of the Boston Public Library

365 Bremen Street, East Boston

 

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

June 12, 2026
Event Date2026-06-12T11:30:00 - 2026-06-12T13:00:00
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