Original Research by School Decision on Staples High School
Staples High School is Westport's sole public high school, serving all grades nine through twelve in an affluent coastal Connecticut town where housing values are substantially above state and national medians and the local economy centers on financial services and professional offices.
The school enrolls a student body that is predominantly white, with smaller shares of Asian, multiracial, Hispanic, and Black students. The free-or-reduced-price-lunch rate was not available in the data, so a reader cannot assess economic diversity from that metric. State testing data for the most recent school year shows proficiency in English language arts in the high-to-moderate range, math slightly lower, and science the strongest of the three subjects. Only one year of results are on record here, so trend direction cannot be determined. A four-year graduation rate and chronic absenteeism figures were not reported, which is common at the high school level when state reporting lags or focuses on district-level aggregates rather than individual schools. The school's website was not provided, so details about course offerings, AP breadth, career pathways, special programs, or day-to-day academic structure are not available to describe here.
The town itself is a mix of old New England character and modern wealth. Downtown Westport along Main Street and the Saugatuck River contains galleries, boutiques, restaurants, and civic anchors including the Levitt Pavilion's free summer concerts, a recently renovated library with maker and co-working spaces, and river-front trails. The Longshore complex offers golf, tennis, sailing, and marina access. Two Metro-North stations provide express service to Manhattan. However, the town remains car-dependent outside the downtown core. Staples High School sits on a separate campus away from downtown, on North Avenue, rather than integrated into the civic center.
Growth is being reshaped by state affordable-housing law. Several new multifamily developments are underway, including the Villages at Saugatuck, a mixed-income project that combines state-subsidized and market-rate units after nearly two decades of litigation. Westport has also adopted inclusionary zoning and an affordable-housing trust to diversify its housing stock, though the town remains among Connecticut's highest-cost communities for both purchasing and renting.
At the district level, three significant changes are underway. The town is investing in a major new Long Lots Elementary School, the costliest school building project in Westport's history, with construction beginning in 2026 and completion expected around fall 2027; this carries a substantial multi-year tax impact. In fall 2025, the district expanded its phone-free policy to include high school, requiring students to keep smartphones and wearable devices off their person throughout the school day. The district has also made artificial intelligence a central pillar of its strategic plan, replacing an earlier focus on collaborative problem-solving, and is rolling out a K-12 AI literacy curriculum alongside a new board policy on AI use.
For families considering Staples, the most actionable questions would be about specific academic programs, AP offerings, and how the school structures pathways for college, career, and technical education, since those details are not evident from the available data. The recent phone-free policy is a clear day-to-day reality to understand. The town's high cost of living is plain, and the ongoing construction and demographic shifts tied to new housing development are worth monitoring if families are considering the area for the medium to long term.
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