State of the
Highways & Bridges

September 24, 2025 2:45 pm – 4:30 pm Hybrid | Greater Boston Chamber of Commerce

Event Details

Hear from Highway Administrator Jonathan Gulliver as he shares updates and future plans for the Highway Division of Massachusetts.

Be in the room to network with fellow members and stakeholders, or join virtually to take part in the conversation.

Tickets

Free to Members & Non-Members

Bridging the Connection: Paving the Way to What’s Next

Join us on September 24 for a FREE and engaging discussion spotlighting the critical work of the MassDOT Highway Division, which designs, constructs, maintains, and operates the Commonwealth’s highways, bridges, and tunnels. This session will explore how the Highway Division collaborates with cities and towns to meet local infrastructure needs and ensure safe, efficient travel for all commuters across the state.

Hear from State Highway Administrator, Jonathan Gulliver, who will share insights into current priorities, upcoming projects, and the strategic vision guiding Massachusetts’ transportation infrastructure. From bridge rehabilitation to highway modernization, this conversation will highlight the innovations and challenges shaping the future of mobility in the region and how it impacts economic development, public safety, and sustainability.

Following the address, Administrator Gulliver will be joined by Diana Szynal, President & CEO of the Springfield Regional Chamber, in a conversation led by James E. Rooney, President & CEO of the Greater Boston Chamber of Commerce, to discuss innovative solutions and opportunities to enhance the future of transportation in Massachusetts.

ABOUT TRANSPORTATION FIRST

The Transportation First series offers a platform to discuss the urgent challenges Greater Boston faces by bringing in experts and changemakers to explore the issues and potential solutions for the future of the Commonwealth. This series will help raise broader awareness among employees and employers who are affected by the transit system every day.

By prioritizing all modes of transportation, we can tackle and mitigate other significant policy challenges, including housing, climate decarbonization and adaptation, economic development, economic opportunity, and education access. Transportation First is not only about transportation, but also about delivering improved, more connected and sustainable solutions that are shaping Massachusetts’ tomorrow.

Questions? Contact us.

Erica Deese

Senior Program Manager

Greater Boston Chamber of Commerce

Email Erica

Speakers

Jonathan Gulliver

State Highway Administrator,
Massachusetts Department of Transportation

Jonathan Gulliver was appointed State Highway Administrator for the Massachusetts Department of Transportation by Governor Charlie Baker in 2017 and reappointed…Read more

See on LinkedIn

Diana M. Szynal

President & CEO,
Springfield Regional Chamber

Diana brings over 20 years of state and local government experience, community outreach, a deep understanding of the legislative process, and workforce advocacy…Read more

Diana brings over 20 years of state and local government experience, community outreach, a deep understanding of the legislative process, and workforce advocacy to her role. Prior to becoming Chamber President, Diana served as the Executive Director of the Franklin County Chamber of Commerce for over three years.

A lifelong Hampshire County resident, Diana spent her formative years in Hatfield and attended the University of Massachusetts Amherst. Her breadth of experience working with local governments and the state legislature began in Hampshire County, where she served as the Municipal Specialist to the Hampshire Council of Governments. Diana went on to gain elected experience, completing three full terms as a member of the Hatfield Select Board, including six years as Board Chair, and she was recently re-elected for her fourth three-year term. Like many elected officials serving in small towns, Diana also serves on other town boards, such as the Capital Planning Committee. She also serves as the Selectboard liaison to the School Department, Police Department, and Council on Aging.

Before joining the Franklin County Chamber of Commerce as Executive Director, Diana spent 16 years as the district director for the late state Representative Peter Kocot in the 1st Hampshire District. Having served in various legislative roles, Diana has developed a deep passion for community and constituent services, helping to solidify her understanding of how the government works to benefit both large and small local businesses.

Diana has served on the Board of Directors for MassHIRE Franklin and Hampshire Counties and the Opioid Task Force of Franklin County, the Franklin Regional Economic Development Initiative, and the Comprehensive Economic Development Strategy Committee, which helped develop the Franklin County Recovery and Resiliency Plan. Much of her work impacted all areas of Western Massachusetts, providing Diana with a deep understanding of the strengths and challenges of the businesses, communities, and organizations in our tri-county area.

Diana went on to gain elected experience, recently completing four full three year terms as a member of the Hatfield Select Board, including nine years as Board Chair. Like many elected officials serving in small towns, Diana also served on other town boards, such as the Capital Planning Committee. She also serves as the Selectboard liaison to the School Department, Police Department, and Council on Aging. She currently serves on the Hatfield Housing Authority.

Diana resides in Hatfield with her husband, Jim. They have three children. Peter is a farmer in Connecticut; Henry resides in Somerville and works for a software company; and their daughter, Hadley, is majoring in health sciences at Quinnipiac University. Diana loves animals and has a black lab rescue named Emmitt, a silver lab named Shelby and a cat named Eleanor. When Diana is not serving her community or spending time with her family, she enjoys cooking, baking, and quiet living amidst the beautiful farm fields in Hatfield.

See on LinkedIn

James E. Rooney

President & CEO,
Greater Boston Chamber of Commerce

James E. Rooney is President & CEO of the Greater Boston Chamber of Commerce, the region’s most influential business association. With Rooney’s…Read more

James E. Rooney is President & CEO of the Greater Boston Chamber of Commerce, the region’s most influential business association.

With Rooney’s commitment and leadership, the Greater Boston Chamber is now the leading convener, voice, and advocate for the region. Strategizing with government leaders, private companies, and public institutions to strengthen the state’s competitiveness, Rooney advances the future of commerce with public policies and legislation that champions dynamic and resilient people, communities, and workplaces.

Before leading the Chamber, Rooney served as executive director of the Massachusetts Convention Center Authority (MCCA), overseeing the development and construction of the Boston Convention & Exhibition Center (BCEC) while leading the management teams of four MCCA-owned facilities. Prior, Rooney served two years as Chief of Staff to Boston Mayor Thomas M. Menino, chairing the Mayor’s cabinet to move forward all aspects of city governance.

Rooney started his public career at the Massachusetts Bay Transportation Authority (MBTA), starting as a track laborer and ending as Deputy General Manager. He served one year as the MBTA’s Acting General Manager during a gubernatorial transition. Using his transportation financing expertise, Rooney led one of the nation’s largest transportation projects, the $15 billion “Big Dig” Central Artery highway project, and he served as Chief Financial Officer at the Massachusetts Turnpike Authority.

Rooney serves in leadership positions on several boards of directors, including the Committee of 100 at the U.S. Chamber of Commerce, Chair of the Association of Chambers of Commerce Executives (ACCE), Board Member of the National Association of Corporate Directors, New England (NACDNE), Co-Chair of the Madison Park Steering Committee, and Member of the Boston Private Industry Council (PIC). Rooney continues to be recognized for his professional and civic contributions, including being named to the list of 100 Most Influential Bostonians by Boston Magazine numerous times, receiving the City of Boston Lifetime Achievement Award for advocacy of the immigrant community, and he was honored with the PCMA Lifetime Achievement Award for his contributions to the global meetings industry.

Born and raised in South Boston, Rooney attended the prestigious Boston Latin School, where he served as President of his graduating class. He graduated from Harvard College with a bachelor’s degree in economics and attended the Boston University Graduate School of Management.

See on LinkedIn

Agenda

2:45 p.m. – 3:15 p.m. | Registration & Networking

In-person guests arrive, sign in at registration, and network with fellow attendees.

3:15 p.m. – 4:30 p.m. | Program

For those joining us in-person and virtually, hear an address from Jonathan Gulliver, State Highway Administrator, followed by a discussion with Diana Szynal, President/CEO of the Springfield Regional Chamber, led by James E. Rooney, exploring the current state and future plans of the Highway Division.

FAQs

What is included in my registration?

Access to a welcoming community of professionals over a great conversation and refreshments!

What should I bring?

An interest in connecting and networking with other professionals. Oh, and don’t forget business cards.

What should I wear?

Please come dressed for your day!

When should I arrive?

For in-person, registration begins a 2:45 p.m., with program starting promptly at 3:15 p.m.

Note: If attending virtually you will be sent the link to join ahead of the program which will begin at 3:15 p.m.

Do I need to register in advance?

We recommend registering in advance to secure your spot! We have a limited number of in-person tickets available due to capacity limits.

Series Sponsor

Greater Boston Chamber of Commerce

265 Franklin Street, 17th Floor, Boston, MA 02110

Get Directions

This is a free event but if you can no longer attend please notify us so we can open up spots for other guests.

The Greater Boston Chamber of Commerce encourages persons with disabilities to participate, and engage fully, in its programs and events.

If you anticipate needing any type of accommodation, including but not limited to, listening devices, closed captioning, large print, wheelchair access, allergies and environmental sensitivities, or if you have any questions about the venue, event format, or virtual platform, please contact us at [email protected].

Become a Member

About Us

Get to Know the Chamber

Member Benefits

Grow Your Business

Membership Directory

Not sure if you’re a member?

Events & Networking

WHAT’S NEXT

Upcoming Events

Engage & Learn

FEATURED EVENT

Premier Event

2026 Pinnacle Awards

EXPLORE OUR PROGRAMMING:

Member Engagement

Maximize Your Membership

Register Now

Membership Directory

Discover fellow Chamber members.

Upcoming Events

Stay Involved

Talent & Workforce

City Awake

Boston’s Future Leaders

Massachusetts Apprentice Network

Women’s Leadership Program

Partnership with Boston Public Schools

Strategic Communication for Better Collaboration

Policy & Impact

GET INVOLVED IN OUR POLICY FOCUS AREAS

Business Climate

Climate & Energy

Health Care

Housing & Development

Talent

Transportation

Foundation

Our Mission

Expanding Opportunity

Foundation Initiatives

Programming That Empowers

Upcoming Events

Get Involved

Become a Member

About Us

Get to Know the Chamber

Member Benefits

Grow Your Business

Membership Directory

Not sure if you’re a member?

Events & Networking

WHAT’S NEXT

Upcoming Events

Engage & Learn

FEATURED EVENT

Premier Event

2026 Pinnacle Awards

EXPLORE OUR PROGRAMMING:

Member Engagement

Maximize Your Membership

Register Now

Membership Directory

Discover fellow Chamber members.

Upcoming Events

Stay Involved

Talent & Workforce

City Awake

Boston’s Future Leaders

Massachusetts Apprentice Network

Women’s Leadership Program

Partnership with Boston Public Schools

Strategic Communication for Better Collaboration

Policy & Impact

GET INVOLVED IN OUR POLICY FOCUS AREAS

Business Climate

Climate & Energy

Health Care

Housing & Development

Talent

State of the
Highways & Bridges