Two modular classrooms, left, have been installed at Long Lots Elementary School, which has the largest enrollment among the town’s five elementary schools. (Photo by George Maddaloni) At right,
Thomas Scarice has been superintendent of Westport’s public schools since July 2020. (Photo by Linda Conner Lambeck)

By Linda Conner Lambeck

WESTPORT — Two days away from when more than 1,000 teachers return to work and a week before the start of the 2023-24 school year for some 5,300 students, there is a sense of anticipation on the third floor of Town Hall where the school district’s administrative offices are housed.

Supt. of Schools Thomas Scarice rushes in from Long Lots Elementary School, where new portable classrooms are installed and being transformed into fifth-grade classrooms.

“Busiest time of the year,” he proclaims of time leading up to the start of the 2023-24 school year on Tuesday, Aug. 29.

New principals have been appointed for two schools this academic year: Brian Byrne, left, at Greens Farms Elementary and Parthena “Penny” Proskinitopoulos at Coleytown Middle.

“So much is going on to make sure we are ready,” he said. “The next week or so is compressed with activity.”

While at Long Lots, Scarice said power company workers were on site, pathways and awnings have yet to be installed and the school district is waiting for final approval of a certificate of occupancy.

“The plan is to have it ready for teacher move-in day on Monday,” he said.

During his visit to the Long Lots campus on Hyde Lane, Scarice took a walk through the adjacent Westport Community Gardens, which he called stunning.

“It’s a community treasure,” the superintendent said.

But it’s a treasure that may or may not be compromised, pending a town decision on whether to rebuild or replace the aging elementary school, which has the largest elementary enrollment in town. Debate over the  community gardens’ fate has generated weeks of controversy in advance of the Long Lots Building Committee’s imminent recommendation of a school construction option.

Regardless of that decision, Scarice said he hopes it’s not at the expense of the gardens.

A mile and a half away at Staples High School, a major summer capital project to replace part of the roof has entered the punch list phase and is reportedly on schedule.

“They did a remarkable job, considering the awful weather. So much rain,” Scarice said.


Focusing now on the new school year, Scarice said his goal is to maintain and build on the foundation set by his strategic plan. The plan calls for students to feel like they belong and have voice as they learn to solve complex problems.

“This is the first year we will see some real movement toward not just maintaining, but aspirational work,” he said.

 Student voices will be amplified — first, with creation of age-appropriate student government or assemblies at each of the district’s eight schools. Those students will meet monthly with their principal and have input into school practices and policies.

At the high school level, the structure will be more formal with students getting the chance to provide regular feedback on their experiences.

District social and emotional learning efforts at the elementary and middle school level will be expanded into the high school as will the concept of growth mindset, where student are taught to see failure as a springboard for growth and developing abilities.

Despite a threatened legal challenge, the district is still pushing forward with a plan to add two non-voting student members to the Board of Education. Scarice said he was assured by First Selectwoman Jennifer Tooker that the challenge is a town issue, not the school board’s.

Once selected by the schools’ administration and board members, the first two students will join the board after municipal elections in November.

“We are also beginning planning stages for a Center for Leadership Development,” said Scarice. The focus would be on student leadership. The first advisory meeting for the center is set next week.


Buses: For the first time in two decades, there will be a new name on the big yellow school buses that traverse town: First Student. The company replaces DATTCO.

The new contractor has set up an office on the Post Road, according to Scarice, and will park buses at schools, for now, while a more long-term bus depot is sought.

Scarice said a significant number of DATTCO drivers are now employed by First Student.

“We have been assured there will be enough bus drivers when school starts,” said Scarice.

Last year, a school bus driver shortage led to a consolidation of some routes and students arriving late to school.

Scarice said First Student is providing new buses, but that they won’t arrive until sometime in October. When they do, parents will get an app that will help them pinpoint pick-up and drop-off times.

A major roof replacement project at Staples High School was carried out over the summer. / Photos by George Maddaloni

Leadership: New principals will take the helm at two of the town’s eight schoolsBrian Byrne at Greens Farms Elementary School and Parthena “Penny” Proskinitopoulos at Coleytown Middle School.

At all schools, Scarice said, parents can expect more communication from principals and teachers.

The superintendent said that with the exception of a couple of specialty areas, the district is also in good shape in terms of staffing compared to other districts.

Curriculum: In line with a new state mandate, this year’s freshman class must complete a financial literacy class to graduate. The district already offers such a course as an elective and it is highly popular, according to Scarice.

Making it a requirement, may limit those electives some students might otherwise have chosen. The requirement is not expected to affect staffing.

Efforts to evaluate district curriculum will continue. It started last year with world languages. Based on recommendations from an outside consultant, instruction will become more proficiency-based and more clarity will be placed on what students should be learning at certain grades.

School board meetings: In conjunction with the start of the new academic year, the Board of Education has changed the usual date for its twice-monthly business meetings from Mondays to Thursdays.

The first meeting under the new schedule is set for this Thursday at 7 p.m. in the Staples High School cafeteria.


How reading is taught: For the time being, how the district teaches students to read will remain as is.

Despite a state law that requires all districts to select from among seven approved reading curriculums, Westport, like two-thirds of districts in the state, applied for a waiver. That was last January.

The district is still waiting for a review of its lengthy application.

“Last we got was a notice that they are going to assign an individual to work directly with districts on their waiver application,” said Scarice. “Here we are in [August] and there is still no clarity on it.”

It’s unclear who the reviewer will be and when the review will occur.

In the meantime, the district plans to continue its approach, which last year produced the second highest third-grade reading scores in the state.

Scarice said he is not worried about this year’s scores.

“We have a lot of internal data that show how effective our plan is,” he said.

Growing enrollment: The upward trend seems to be on the mark.

The new “FitCore Extreme” ropes course/play area, funded by federal pandemic relief funds, has been completed at Coleytown Middle School. / Photo by George Maddaloni

Last June, the school district’s prediction of needing 123 elementary school classrooms in the fall stood at 119 sections. It has since filled out to 123 sections.

“The numbers, overall, are what we anticipated,” Scarice said.

First 30 days: Started last year, a focus on fostering staff-student connections during the first month of school will continue. The idea is to strengthen the social and emotional well-being of students and make them feel they belong.

Scarice said the approach was embraced last year. Every school has a plan.

This year, the high school plan includes a first day schedule change. Only freshmen will report in the morning next Tuesday. Sophomores through seniors will come for the second part of the day.

The idea is to give freshmen a chance to acclimate.


Redistricting: The Board of Education and community are expected to tackle the issue of redistricting this school year.

A tumultuous topic that ended in school boundaries remaining the same the last time the town tried to do it,  Scarice said he doesn’t expect the process to be as rough this time because of the time built into the process.

By this time next year, Scarice expects the community to know the direction the district is headed as it tries to redraw boundaries for elementary, and potentially, middle schools. Scarice’s timetable calls for the board to decide on a plan by November 2024, which can be built into the budget and executed for the fall of 2025.

By this time next year, the town will also have the wheels in motion to rebuild or replace Long Lots. Scarice said a brand-new Long Lots remains his strong recommendation.

The national conversation: Last year, the appropriateness of some books in the Staples library was challenged, as well as district efforts to make school equitable for all students

Scarice expects those issues to remain topics of debate.

“I think what we are looking at is a national conversation,” said Scarice. A conversation he predicts will continue as the 2024 presidential election draws closer.

“Public schools keep working their way into that conversation,” the superintendent said. “But I have to say, as much as it can be an emotional topic, I think that locally there is a deep commitment to the success of the Westport public schools and kids.”

He also expects his good relationship with both school board and town officials to continue.

The key, he said, is communication, transparency and owning up to mistakes when they are made.

During his annual job evaluation in June, Scarice said school board members were clear they would like him to remain the district’s top administrator a long time. The board in June unanimously extended his contract to June 2026.

The sentiment appears mutual.

“Honestly, I can’t see myself anywhere else right now, I just can’t,” he said. “I feel I thrive in a community like this. It suits me. I’m an ambitious guy. This is an ambitious community. For me, it’s a perfect match.

Freelance writer Linda Conner Lambeck, a reporter for more than four decades at the Connecticut Post and other Hearst publications, is a member of the Education Writers Association.