The coming election is crucial for Westport.
Voters have several ways to assess candidates. But it’s not always convenient to get to to debates or forums.
Mailings don’t really dig into issues.
And yard signs are not exactly profound.
Today, “06880” introduces a new feature: “Where We Stand.”
Once a week, between now and Election Day, we’ll ask candidates for 3 important boards — Selectmen/women, Planning & Zoning, and Education — one specific question.
We’ll print their responses verbatim. (And we’ll change the order we run them each week, to be extra fair.)
An informed electorate is the greatest bulwark of democracy. Westporters have always participated avidly in our town government.
“06880” is proud to do our part this fall to help.
This week’s question for the Board of Selectmen/women is: “What is the single most important issue facing Westport right now, and how will you address it?”
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Democratic Party-endorsed candidates Kevin Christie and Amy Wistreich say:
Our top priority will be Westport’s infrastructure. Whether it’s solving traffic problems, upgrading parking at “Harder Parking” (aka Parker Harding), fixing a fast deteriorating Cribari Bridge, or building a school, Westporters deserve leadership that prioritizes essential projects, and then gets them done.
We will bring the community together to discuss our spending priorities. We are not talking about just “listening.” Reaching consensus on Westport’s infrastructure agenda will make sure taxes don’t have to rise unnecessarily, and will guarantee that the most pressing capital infrastructure projects are pursued with appropriate urgency; while respecting the process and citizen input.
We will weigh in on the most transformative proposed project in modern Westport history: Saugatuck. We will help guide the community conversation to a better answer for development in Saugatuck than The Hamlet. Together, we will find the path to a real solution.

Kevin Christie and Amy Wistreich
We all know that downtown parking is a growing problem. As your selectmen, Amy and I will seek a comprehensive plan for downtown which leverages the work of the Downtown Plan Implementation Committee, and includes ideas from business owners, too.
I will hold community discussions with neighbors to seriously consider other options such as a parking deck with liner retail and a “green roof” with passive recreation. We can solve the parking problem for a generation or more. We also need more sidewalks, and need to make Westport more walker- and cyclist-friendly.
We will fix the Cribari Bridge. In fact, we are already working with our state delegation. We will figure out how to maintain its charm while making it safe, while exploring creative options to keep large trucks off our local roads. We will consider local control of the bridge, too.
When elected, we will evaluate creating the role of director of economic and community development, a position that Fairfield has employed to great success. Business and community concerns are entwined, and both benefit when there’s someone dedicated to building consensus on how to move forward and facilitating those outcomes.
We can add transportation issues to this position’s portfolio, so that parking and traffic implications are considered when making big infrastructure decisions.
Ultimately, addressing Westport’s significant infrastructure investment choices requires leadership skilled in analysis, planning and project execution, as Amy and I have demonstrated in our careers and public service.
However, the most important talent is a willingness, even a passion, for listening to others. Our selectpeople should be confident in their vision for Westport, and prepared to persuade others on the merits. But they should also be humble, open to good ideas regardless of the source, so that the outcome for Westport is based not only on the best information and strategy, but also a range of perspectives.
My door will always be open to all Westporters. Only by working together can we fashion a plan that enhances this great town in a responsible way. That’s what we’ll do from Day 1.
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Republican Party-endorsed candidates Don O’Day and Andrea Moore say:
The most important issue facing Westport today is our inability to move projects forward.
Too often, our review and decision-making process is polarized and slow. Even small matters are delayed — or avoided altogether. Extensive public input and hard questions are always appropriate; however, never-ending requests for additional data can be decision avoidance. Nothing happens without decisions, and inaction ultimately hurts all Westport residents.

Andrea Moore and Don O’Day
Here are some of the of the most pressing issues requiring more action in Westport:
Affordable Housing and 8-30g
With the shortage of affordable housing, we are routinely targeted by developers exploiting our 4% ratio of affordable units that is well below the state’s 10% mandate. This shortfall leaves us vulnerable to dense apartment projects, with little zoning oversight under 8-30g. Reaching 10% is not realistic, but we can secure a new 4-year moratorium based on projects already in the pipeline (e.g., Post Road West and Hiawatha Lane).
What we will do? Double down on efforts to identify land or buildings for affordable housing. Westport has strong partners in the Affordable Housing Committee, Housing Authority, and Planning & Zoning Commission, and we must be ready to act quickly when opportunities arise. We should also encourage “friendly” 8-30g projects, as Darien has done, by working with developers willing to collaborate with the town.
Saugatuck Development
The future of Saugatuck remains unsettled, with the choice between no action, a thoughtful development, or a large 8-30g looming.
What we will do? Development with P&Z oversight is better than a dense 8-30g project with little control. We must resolve outstanding concerns through open dialogue. We cannot afford stalemate — we must talk and negotiate. It is better to have input than to relinquish control.
Senior Housing
Seniors face a severe lack of housing options. Single-level homes and condominiums are especially scarce.
What we will do? Establish a first selectman’s task force, with members from the Board of Finance, P&Z, Y’s Men and Women, and other stakeholders. Its charge: (a) expand senior housing inventory (retrofitting existing office space?), (b) incentivize developers to include more senior-friendly designs, and (c) explore financial tools such as tax abatements on new projects.
Downtown Parking
Parking downtown remains a challenge, and Parker Harding is overdue for significant improvements.
What we will do? Follow the Downtown Plan Implementation Committee’s structured 4-part strategy to address parking challenges and address ADA issues that have been brought up. No solution should be off the table.
Capital Projects
Over $400 million in proposed capital projects — and that’s before bonding costs. Every sponsor believes their project is most urgent.
What we will do? Re-prioritize the capital forecast by ranking projects high, medium, or low priority, with the understanding that low-priority projects will not move forward. Apply a simple rule: If a building is functional, dry, warm in winter, and cool in summer, it’s not an immediate priority. Further, the Capital Project list is a Westport list, not a school versus town list,
Traffic is terrible
Every part of town is impacted by increased volume of cars.
What we will do? We are not going to reduce the volume of cars, but we can explore remote monitoring of variable choke points as they develop. We can use technology and adjust traffic light timing to allow for more intelligent flow. Another idea is to guide people on how to make left hand turns onto Post Road from Wilton Road.
Westport will always be able to solve issues by working together. The O’Day/ Moore team has experience leading collaboratively, and a visible and proven track record of success. We will be ready on day one because we have done it before.
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Independent Party-endorsed candidate David Rosenwaks says:
The most important issue facing Westport today is a need for greater transparency and accountability in our town government. This challenge has shaped how decisions are made, how residents experience our town, and to what extent people feel that their voices truly matter. I have had hundreds of conversations with friends and neighbors, and have heard a consistent theme: many residents feel unheard and undervalued.
As first selectman, I will lead with transparency as my guiding principle. Transparency means more than posting documents online or holding meetings that check a box. It means creating a culture where people feel welcomed into the process rather than shut out, where residents are proactively informed, and the rationale for decisions is clearly explained. It means treating residents as true partners in government, not obstacles to be managed.
Accountability is the second essential piece. Westport deserves leadership that is accountable to everyone, not to one faction or interest group.

David Rosenwaks
Accountability means acknowledging mistakes and correcting them. It means being responsive to residents by answering their questions and explaining the reasoning behind choices, so people understand not just what was decided but why.
Accountability also means making decisions after listening to all sides, not just the loudest voices, while also standing by those choices because they were made with fairness, openness, and the long-term best interests of our town in mind.
Modernizing the way our town uses technology is central to achieving this goal. By upgrading our systems and making information easier to access, residents will no longer have to search or wait for answers. They will be able to see clearly how decisions are made, and where their tax dollars are going.
The issues Westport faces are complex, and impact every household. From capital improvements to our schools and infrastructure, to sustainability and resiliency planning, to affordable housing, traffic, public safety, and the community gardens, every one of these issues requires collaboration with residents.
Westport’s strength comes from its people. Our town is full of engaged, passionate, and creative residents who want to contribute to the town’s future.
But when people feel excluded, their energy and talents are wasted. A more transparent and accountable government will not only restore confidence in leadership, but it will additionally invite more residents to participate and share their ideas.
By creating clear pathways for involvement, whether through modernized technology, brown bag lunches, weekly online video updates, or encouraging participation in commissions and committees, we can make it easier for Westporters to take part in shaping the future of the town while also respecting the incredible history that got us to this point.
My commitment as your first selectman will be to lead in this way: to listen, to communicate openly, to explain decisions clearly, and to be accountable to the residents of Westport. By trying to accommodate as many interests as possible during each decision-making process, our results will better reflect the shared values of our town.