The state of the town is “fabulous.”
Our schools are in very good shape too.
Those assessments, from 1st Selectwoman Jen Tooker and Board of Education chair Lee Goldstein, were delivered to several dozen residents this afternoon, at the annual “State of the Town” meeting at the Westport Library.
The Sunrise Rotary and Westport Rotary Clubs co-sponsored the event.

Part of the Trefz Forum audience at today’s State of the Town event.
Tooker repeated a familiar theme: Westport is “the best place to live, work and play in the region.” Goldstein added “and learn,” an idea the 1st selectwoman quickly adopted.
Tooker said that that her administration’s “north star” is that this is a town where everyone feels welcome. She cited the “collaboration, dedication and energy” of town employees, board members, business owners, non-profit leaders and residents as essential to that feeling.
She cited her top 5 priorities:
- Traffic and pedestrian safety
- The Longshore Capital Improvement Plan
- Revitalizing downtown
- Flood and stream mitigation
- Support of the entire community’s emotional health and well-being.

1st Selectwoman Jen Tooker illustrated her remarks on traffic with a familiar photo: the North Avenue back-up by Bedford Middle School.
Tooker noted the importance of “diverse and affordable housing.” She also announced an upcoming initiative to help grow “the local ecosystem of entrepreneurs in technology and related fields.”
In her opening remarks, Goldstein described the “explosive” elementary school population growth since 2019: 262 students. That 12% increase is not mirrored in any neighboring district.
She emphasized the Westport Public Schools’ focus on school culture, well-being and mental health, and a push to give more voice to students. The goal is to “affirm and value all students, so they feel they belong to their school, and their school belongs to them.”
Of course, Goldstein said, the Board of Ed pays great attention to academic achievement, and to upcoming facility needs at Long Lots and Coleytown Elementary Schools.
Meanwhile, unequal spikes in enrollment mean the Board is looking at rebalancing the schools. They’re taking “a measured, careful approach, while recognizing its urgency.”

This slide from Board of Education chair Lee Goldstein showed recent budget efficiencies.
Attendees asked Tooker about a variety of subjects. They included:
- Connecticut’s “looming trash crisis.” (Department heads are collaborating; Sustainable Westport plays an important role; everyone should consider composting.)
- The Hamlet at Saugatuck development. (As First Selectwoman, she sits on the Traffic and Sewer Authority, so she cannot speak about it before the issue comes before those bodies.)
- Saugatuck River dredging. (The Army Corps of Engineers is deciding where to dispose of the silt.)
- Leadership. (“Every decision I make, makes someone unhappy. My job is to listen to and respect everyone, then make the best choice for as many people as I can, look them in the eye and tell them why I made it with grace. Those who scream the loudest should not win the day.”
- The logpile at the Post Road/Roseville Road corner. (It’s in litigation.)
Questions for Goldstein included:
- School start and end times. (The Board of Education recognizes the issue; it will be part of the new transportation contract.)
- The budget. (“We try to keep any cuts out of the classroom.”)
- Diversity, equity and inclusion. (“The work we do is in everyone’s best interest. The majority of the Board supports this work.”)
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From right: 1st Selectwoman Jen Tooker, Board of Education chair Lee Goldstein, State of the Town moderator Tony McDowell. (All photos/Dan Woog)