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Annual Enrollment Benefits Fair

Get one-on-one support with your benefits during Annual Enrollment (April 28–May 16). Talk to plan representatives, ask questions, and get help enrolling — no registration needed.

May 1, 2025
2025-05-01T15:00:00 - 2025-05-01T18:00:00

If you're a benefits-eligible City employee or retiree, Annual Enrollment is your once-a-year opportunity to enroll in, change, or cancel your health insurance coverage without a qualifying life event. This year’s enrollment window is April 28–May 16, 2025.

Join us at an upcoming Benefits Fair to:

  • Ask questions about your coverage options

  • Speak directly with representatives from our health, dental, vision, and life insurance providers

  • Pick up enrollment forms and plan materials

  • Submit your completed paperwork (if ready)

📅 No registration required — stop by anytime during fair hours!

May 1, 2025
2025-05-01T15:00:00 - 2025-05-01T18:00:00
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Suits and Smiles

June 3, 2025
  • 11:00am - 12:30pm
    Repeats monthly on Tuesday, but only the first and the third instance of this set, starting from April 15, 2025, until April 7, 2026
  • 30 Dimock st.
    2nd Floor
    Roxbury, MA 02119
  • Contact:
    Rechelle Hypolite
  • Price:
    FREE
  • Neighborhood:
    Roxbury
  • Posted:
2025-06-03T11:00:20 - 2025-06-03T12:30:20

Register now to schedule your free appointment and visit the ORC Workwear Wardrobe for FREE professional clothing and essential job-readiness tools!

Held on the 1st and 3rd Tuesday every month! 11:00 a.m. - 12:30 p.m.

Dress for success updated flyer

June 3, 2025
  • 11:00am - 12:30pm
    Repeats monthly on Tuesday, but only the first and the third instance of this set, starting from April 15, 2025, until April 7, 2026
  • 30 Dimock st.
    2nd Floor
    Roxbury, MA 02119
  • Contact:
    Rechelle Hypolite
  • Price:
    FREE
  • Neighborhood:
    Roxbury
  • Posted:
2025-06-03T11:00:20 - 2025-06-03T12:30:20
Last updated:

Financial Literacy Workshops (In Collaboration with TD Bank)

Want to take control of your finances?

April 16, 2025
2025-04-16T12:00:55 - 2025-04-16T13:30:55

Join us for an informative workshop hosted in collaboration with TD Bank. Learn practical tips for better money management, budgeting, saving, and more!

Financial Literacy Workshop Flyer

April 16, 2025
2025-04-16T12:00:55 - 2025-04-16T13:30:55
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Economic Empowerment Workshop

April 14, 2025
2025-04-14T14:00:44 - 2025-04-14T15:30:44

Join us for an empowering workshop hosted in collaboration with Harvard Transactional Law Clinic! Gain Practical financial skills and strategies to take control of your future. Don't miss out let's build a stronger financial foundation together!

 

Economic Empowerment Workshop Flyer

April 14, 2025
2025-04-14T14:00:44 - 2025-04-14T15:30:44
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CDL License Workshop (in collaboration with Emerge Careers)

A Free CDL program for MA residents with a history of criminal justice involvement. 

April 11, 2025
2025-04-11T12:00:17 - 2025-04-11T14:00:17

Learn about this free CDL program for MA residents with a history of criminal justice involvement: incarceration, probation, parole, diversion programs, ect. 

EmergeCareer ORC Flyer

April 11, 2025
2025-04-11T12:00:17 - 2025-04-11T14:00:17
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Resource Fair: Second Chance Month

April 9, 2025
2025-04-09T10:00:00 - 2025-04-09T14:00:00

The Mayor’s Office of Returning Citizens, in collaboration with the Office of Black Male Achievement, is excited to invite you to a Resource Fair in celebration of Second Chance Month. This event will provide valuable resources in areas such as employment services, housing, health, mental health, recovery, advocacy, CORI sealing, and much more!

Event Details:

Date: April 9, 2025

Time: 10:00 a.m. – 2:00 p.m.

Location: Reggie Lewis Center, 1350 Tremont Street, Boston, MA 02119

To ensure your spot at the event, please register.

Register Now

We look forward to seeing you there! If you have any questions, please feel free to reach out to Eric James, Employment Specialist, at 617-777-1355 or via email at eric.james@boston.gov.  

flyer

April 9, 2025
2025-04-09T10:00:00 - 2025-04-09T14:00:00
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Opportunity Youth Career Pathways Virtual Panel

April 9, 2025
2025-04-09T12:00:00 - 2025-04-09T13:00:00

Please join us for a virtual panel discussion of effective models for engaging and supporting opportunity youth at different stages of their career and educational journeys. The panel will include:

  • Rashad Cope (Moderator), Deputy Chief of Worker Empowerment
  • Tanisha DeLeon, Deputy Director, YOU Boston
  • Kelly Folsom, Director, Bridge-to-Training Programs, X-Cel Education
  • Davo Jefferson, Executive Director, PowerCorps Boston

Presented by the Worker Empowerment Learning Lab and the Opportunity Youth Collaborative.

April 9, 2025
2025-04-09T12:00:00 - 2025-04-09T13:00:00
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DigLit 2.0 Launch and Panel

March 20, 2025
2025-03-20T10:00:00 - 2025-03-20T12:00:00

The Worker Empowerment Learning Lab and Congresswoman Ayanna Pressley will launch the DigLit 2.0 initiative on Thursday, March 20 at the East Boston YMCA on Ashley Street. DigLit 2.0 is a capacity-building initiative aimed at enhancing the ability of occupational training providers to deliver digital literacy. The launch event will feature a moderated panel discussion on how digital technologies and AI are shaping job roles, changing workforce needs, and driving successful alignment efforts between employers and training providers.

View the event agenda here.

March 20, 2025
2025-03-20T10:00:00 - 2025-03-20T12:00:00
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BCYF Hiring Day March 8

Stop by our job fair and learn about and apply for jobs working for Boston Centers for Youth & Families!

March 8, 2025
  • 11:00am - 2:00pm
  • BCYF Shelburne Community Center
    2730 Washington Street
    Roxbury, MA 02119
  • Contact:
    Francesska Jean-Pierre
  • Price:
    FREE
  • Neighborhood:
    Roxbury
  • Event Type:
  • Posted:
2025-03-08T11:00:00 - 2025-03-08T14:00:00

Stop by our job fair. Learn about and apply for jobs working in the City of Boston’s community centers and pools! Jobs available include Lifeguards, Staff Assistants, Athletic Assistants and Directors, Human Resources Director, Program Supervisors, Building Assistants and Managers, Maintenance Workers/Custodians, Youthworkers, Program Assistants, Camp Joy Counselors, Supervisors and Nurses. City of Boston residency is required for all jobs except Lifeguards and Camp Joy. Pre-registration preferred but walk-ins welcome.

Register

March 8, 2025
  • 11:00am - 2:00pm
  • BCYF Shelburne Community Center
    2730 Washington Street
    Roxbury, MA 02119
  • Contact:
    Francesska Jean-Pierre
  • Price:
    FREE
  • Neighborhood:
    Roxbury
  • Event Type:
  • Posted:
2025-03-08T11:00:00 - 2025-03-08T14:00:00
Last updated:

Parking Enforcement Job Fair

Boston is hiring Parking Meter Supervisors! 

February 7, 2025
  • 10:00am - 4:00pm
  • Civic Pavilion at City Hall
    5 Congress Street
    Boston, MA 02203
  • Contact:
    Transportation
  • Price:
    FREE
  • Event Type:
  • Posted:
2025-02-07T10:00:00 - 2025-02-07T16:00:00

The Transportation Department will host a job fair for open Parking Meter Supervisor positions. You can apply in-person at the event or on the City's website at this link

February 7, 2025
  • 10:00am - 4:00pm
  • Civic Pavilion at City Hall
    5 Congress Street
    Boston, MA 02203
  • Contact:
    Transportation
  • Price:
    FREE
  • Event Type:
  • Posted:
2025-02-07T10:00:00 - 2025-02-07T16:00:00
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