Summary:
The Trumbull School District is home to two middle schools — Madison Middle School and Hillcrest Middle School — serving grades 6–8 in one of Connecticut's strongest districts, ranked 23rd out of 153 districts statewide (85th percentile, 4 stars). Both schools sit well above state averages across every subject and grade level, making this an exceptionally strong area for middle school students.
Hillcrest Middle School is the clear standout in the district. It has earned a 5-star rating for three consecutive years, ranking 15th of 258 schools in 2025–2026, 11th of 252 the year before, and 23rd of 250 in 2023–2024. Hillcrest leads in every academic category, with average proficiency of 78.0% in ELA and 76.5% in Math, compared to Madison Middle School's 73.0% and 65.1%. Its chronic absenteeism rate is just 4.1%, far below Madison's 8.1% and the state average of 16.4%. Notably, Hillcrest achieves this while serving a slightly higher percentage of students eligible for free/reduced-price lunch (22.1% vs. 20.2%). Madison is still a strong school, ranking 38th of 258 statewide (85th percentile) and nearly tying Hillcrest in 7th grade ELA, but it trails significantly in 8th grade math (61.6% vs. 76.8%) and shows a larger drop between 7th and 8th grade performance.
The data suggests attendance is closely tied to outcomes: Hillcrest's lower chronic absenteeism aligns with its stronger academic results. Madison's 8th grade dip may point to a transition challenge or a weaker cohort, while Hillcrest remains stable from 7th to 8th grade. Both schools slipped slightly in the most recent rankings — Madison from 30th to 38th and Hillcrest from 11th to 15th — but they remain in the top 6% and top 15% statewide, respectively. With nearly identical per-student spending ($16,462 at Hillcrest vs. $16,244 at Madison) and similar student-to-teacher ratios (13.7 vs. 14.3), school-specific practices appear to be driving Hillcrest's edge. For parents, both schools are excellent options; Hillcrest, however, is the stronger all-around performer.
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