By Meghan Muldoon

WESTPORT — First Selectwoman Jennifer Tooker and Board of Education Chair Lee Goldstein gave residents an update on education issues, sustainability initiatives, infrastructure improvements and community support programs during the 8th annual “State of the Town” presentation Sunday at the Westport Library.

Strides on traffic and pedestrian safety

A highlight of the year past, according to Tooker, is that the task force dedicated to traffic and pedestrian safety has acted on more than 50 community-reported concerns. She also emphasized the town’s progress in upgrading intersections and sidewalks, citing the rise in the Sidewalk Condition Index from a 48 in 2018 to 71 in 2024. She noted her goal is to reach 80 on the index by the end of 2025.

To reassure residents their concerns about reckless driving are being addressed, Tooker reported that Westport saw a 54 percent increase in traffic stops in 2024. “Our police force is actively out there, serving you and trying to keep our roads safe. I can assure you, this work is never done,” she said.

Longshore plans teed up

Regarding the status of capital improvements at Longshore Club Park, Tooker identified the renovation and relocation of the maintenance building as a priority. Plans for a new maintenance building — the first project in the overall Longshore Capital Improvement Plan — sparked questions about its cost and proposed relocation at recent Board of Finance meeting.

“It’s not a glamorous part of the plan,” the first selectwoman said, “but that maintenance facility, not only is an eyesore, it’s not up to code and it sits on prime property in the middle of our park.”   

She also confirmed that the Inn at Longshore, currently under renovation, will reopen in April.

Downtown parking

Tooker said the town is “shovel ready” on plans to revamp parking at Parker Harding Plaza, but will not be moving forward until a more comprehensive, strategic overall plan for downtown parking is complete. She also noted that a recently conducted study found that a parking structure is not needed downtown at present.  

According to Tooker, flood mitigation and stream management remain pressing concerns because of Westport’s geography, with seven streams, the Saugatuck River, Long Island Sound and extensive wetlands. “We are a very wet town. It took us decades to get where we are now, and it’s going to take decades to make a change,” she noted.

Affordable housing … on Baron’s South?

To diversify the town’s housing stock, Tooker highlighted plans to convert five buildings on Baron’s South property, including the Golden Shadows mansion, into multi-family residences that will be deemed affordable. A text amendment to facilitate those plans is on the agenda of Monday’s Planning and Zoning Commission.

The town’s newly constituted Affordable Housing Committee will help ensure the Affordable Housing Trust Fund, which currently holds over $800,000, is spent appropriately, she said.

Social service investments

Tooker also highlighted Westport’s continued investment in facilities serving its most vulnerable residents. Noting recent completion of renovations at the Gillespie Center emergency shelter, community kitchen and food pantry, she reported that work progressing on Susie’s House, a residence for young women in need.

To support residents’ mental health, Tooker announced a new partnership with Silver Hill Hospital to offer free mental health assessments to Westporters within 24 to 48 hours — an initiative designed to address the difficulty of securing initial evaluations in Fairfield County.

The first selectwoman also outlined Westport’s sustainability efforts, including the “Skip the Stuff” campaign, which encourages restaurants to reduce waste by only providing utensils, napkins and condiments upon request. The town has also electrified a portion of the Police Department’s fleet, including bikes and a dune buggy, and geothermal heating is planned at the future Long Lots Elementary School. She also highlighted Town Hall’s paperless initiatives and efforts to increase open space.

Consolidated public safety complex considered

Looking to the future, Tooker discussed her hopes for a combined public safety complex housing police, fire and emergency medical forces, and invited people in the audience to attend an open house this week to review and comment on conceptual plans for the facility. The meeting will take place at 7 p.m. Thursday at the Westport Center for Senior Activities, 21 Imperial Ave.

In response to a question from the audience about federal funding cuts for DEI (diversity, equity and inclusion) initiatives by the Trump administration, Tooker assured residents that the town does not receive federal funding and would not be affected by those changes. 

Tooker evaluates “options” on political future

Regarding her own political future, amid speculation about a potential run for governor in 2026, Tooker sidestepped the question Sunday.

“I’m evaluating some options on a going-forward basis, but we’re here today to talk about Westport, and I want to stay focused on Westport today,” she said.

School district ensuring excellence

At her turn at the podium, Goldstein emphasized Westport’s commitment to excellence in education, citing that 88 percent of last year’s Staples High School graduating class reported satisfaction with their post-high school plans. 

“We are proud that our students leave Westport public schools equipped for what comes next and happy and excited to begin their next chapter,” she said.

Student engagement highlighted

She highlighted the resurgence of student government at Staples High School, including the development of the school’s first-ever school-wide Field Day and the second year of two student representatives serving as non-voting members of the Board of Education.

Goldstein mentioned that Senior Walks, a new tradition where graduates return in caps and gowns to their elementary schools, has been well received. Additionally, Goldstein reviewed ongoing efforts to address bullying and discrimination through the “No Place for Hate” program, an initiative designed by the Anti-Defamation League to foster inclusivity and respect.

Districtwide course evaluations

Goldstein also announced that for the first time, course evaluations will be administered to all students in grades three through 12 to provide feedback on curriculum and teaching methods. Goldstein also celebrated the national recognition of Westport public schools as a model district for evidence-based literacy instruction.

Looking ahead, the school board cited plans, awaiting financial approval, to upgrade Staples High School’s auditorium, focusing on critical safety concerns related to rigging and lighting. Also under consideration are improvements to the auditorium sound system and the hall itself, which has remained unchanged for over 30 years.

Plans for new Long Lots taking shape

Goldstein said plans to build a new Long Lots Elementary School continue to move forward, with more details on costs and site plans expected in the coming months. The town is targeting a September 2027 opening.

Goldstein also addressed questions about a potential ban on students’ cellphones at Staples High School. Currently, cellphones and wearable technology are prohibited at Westport’s elementary schools and restricted to lockers or back packs in the middle schools.

Noting that Wilton High School recently implemented a cellphone ban, Goldstein predicted that by next year, Westport’s prohibition on cellphone use during the school day will be extended to the high school as well.

Meghan Muldoon is a freelance writer.