It faces its fair share of challenges, but Westport’s school district is blessed with good kids, caring teachers, robust and passionate community support, and plenty of optimism.

As school officials prepare to rewrite the district’s five-year strategic plan that expires at the end of the school year, Superintendent Fran Roy said she is optimistic that Westport can address its shortcomings, and build on its many successes, in the years ahead.

“If we can do all of this really well, which is the complexity of schooling, then we’re going to have a thriving school community,” she told members of the school committee last Wednesday, Jan. 7.

‘Entry plan’

Since shortly after she started on the job in July, Roy sought to learn as much as possible about the district and town as she prepared an “entry plan” to inform district officials as they look toward the next strategic plan. She spoke to dozens of teachers, students, staff, parents and boosters, attended as many extra-curricular functions as possible, held “listening sessions” with constituents and was a regular sight at many games.

The results went into an entry plan report she presented to the committee last week. It lists strengths and ‘concerns’ she found in five key areas: community, human capital and operations, curriculum, student support and aspirations.

Here’s what she found in each:

Community

“We have tremendously good, dedicated people here who just want the best,” she told committee members. “Community pride and community communication is strong; the parents, the teachers … everybody talked about this tight knit small community.”

The report expounds on that, highlighting the enthusiasm and pride of stakeholders and the wide range of community partners, like the Westport River Watershed Alliance and others that support and work with the schools. It singles out PTOs, boosters and the Westport Education Foundation, and the town-funded school resource officers (SROs) that she wrote are “embedded into the everyday fabric of school life.”

There are concerns, she wrote.

Out-of-state, private and vocational schools “reduce school pride and enrollment,” and the fact that families are looking for more streamlined and consistent means of communication” about their children’s academic lives.

“There’s this narrative about other folks not understanding how good Westport is, and so they take their kids out. If they knew more, then they would understand and they would want to keep their kids in the district.”

Ironically, one concern was borne out of the large number of extracurricular opportunities presented to kids every day. Partnering organizations like the WRWA and others, she said, “expressed the need for coordination of events, to reduce the number of overlapping activities.”

Capital and operations

This section dealt with staff quality, facilities and resource management. Overall, conversations she had with community members pointed to the teaching staff as “amazing, creative and supportive.”

Special education teachers were showered with praise for building the department over the last few years, and she wrote that the district has a hard-working, resourceful staff.

As for Westport’s investment in facilities and technology, they have borne positive results, including better safety for students and more efficient use of technology.

There are a few improvements that need to be made, she added. She cited the need to streamline more labor intensive functions, and noted that some teachers expressed frustration with outdated technology at the middle high school.

Curriculum

Dr. Roy told committee members she has been impressed with the sheer number of programs and classes available to students, whether they plan to attend college or not.

Music and drama programs and other after school offerings are excellent, she learned, and “observations indicate that foundational literacy skills (are) a consistent priority” across the Macomber and Westport elementary schools.

STEM teachers are innovative, she said, offering new programs to reach all kids regardless of their plans after high school, and the “seeds of experiential learning” exist.

However, there are areas in need of improvement across the board, she found. Students need more hands-on training and career readiness programs. The district’s “career pathways” curriculum, which seeks to prepare students for emerging job markets and real world skills, “is still in its infancy (and) more programming is needed.”

There could be a better, more cohesive vision guiding the development of curriculums, and her study found that the lack of common planning adds to inconsistent curriculum development. In addition, teachers want more professional development relevant to their areas of focus.

Student performance also lacks in some areas, she wrote: Those from low-income backgrounds are 50 percent less likely to meet or exceed expectations on state tests, and standardized testing achievement lags in grades 3 through 8.

Student support

Roy highlighted the good work being done by special education teachers, wrote that early literacy work is improving, and noted that the district’s small size enables not only more personalized attention, but also a more welcoming feel for students with anxiety or special needs. That community feel ensures that kids “receive individualized support and are not overlooked” as might be the case in a larger district.

But she also found that the district’s implementation of special education requirements could still improve. Some interviewees asked for more therapeutic supports for students, those who struggle with learning, especially math, and asked that services for students in need “be provided proactively rather than waiting for students to qualify.”

Some stakeholders asked for more outdoor/recess time, less screen time, better transportation and facilities to support recreational opportunities for teens, and said that “some students struggle in school due to complex social and emotional needs.”

Aspirations

Looking ahead to the future, Roy found that stakeholders consistently put kids first, and want that to continue: They “want students to graduate with a clear vision and multiple pathways to success, including a plan for the future, not just a diploma.”

Others hope for increased opportunities for those kids who don’t plan to go to college, and want students and stakeholders to “develop lifelong connections to Westport, give back to the community, and foster a sense of community pride.”

What’s next

Roy’s blueprint will be discussed heavily over the coming months as district officials work to write a new strategic plan for the next five years.

“It’s very clear there are challenges that are being addressed right now,” Roy said, but also many good signs and much good work already being done — “I look forward to the conversations about the direction we take as we get in to the (2026-27) school year.”

Committee members seemed impressed and ready to go. Said Caitlin Sampers:

“As a parent I’m happy to raise my kids here.”