Westport School District

The Westport School District serves 8 schools (5 elementary schools for grades K–5, 2 middle schools for grades 6–8, and 1 high school for grades 9–12) in an affluent Connecticut community, enrolling about 5,161 students and ranking 10th out of 153 districts statewide. All eight schools rank in the top quartile of Connecticut schools, with most in the top 10–15% statewide, making this one of the strongest public school districts in the state.

Staples High School is the district's only high school and its flagship, ranked 3rd in Connecticut with a 98.5% graduation rate, 90.5% ELA proficiency, and 73.2% math proficiency. At the middle school level, Coleytown Middle School (ranked 5th) outperforms Bedford Middle School (ranked 9th) in nearly every subject and grade, despite Bedford having slightly smaller classes. Among elementary schools, Saugatuck Elementary School leads the pack, climbing from 39th to 24th in the state, with strong 4th grade scores (87.1% ELA, 88.2% math) and the district's lowest free/reduced lunch rate at 1.52%. Long Lots School stands out for attendance, with just 1.1% chronic absenteeism — the lowest in the district and far below the 16.4% state average.

The schools to watch are Coleytown Elementary School and King's Highway Elementary School, which have fallen from the top 25 to 77th and 52nd, respectively. Math proficiency is the district's relative weakness — Staples' math scores trail its ELA by 17 points. Notably, spending doesn't predict performance: Staples spends the least per student ($20,796) yet ranks 3rd, while Coleytown Middle spends the most ($27,339) and delivers top results. Chronic absenteeism is remarkably low across the district, ranging from 1.1% at Long Lots to 9.2% at Staples, and student-teacher ratios are favorable (9.8–11.6). Even with recent declines at two elementary schools, Westport remains an elite district.