Best Middle Schools in Monroe, CT

Monroe, Connecticut is served by a single public middle school, Jockey Hollow School, which enrolls 765 students in grades 6–8 as part of the Monroe School District. With a student–teacher ratio of 13.7 and a free/reduced lunch rate of 18.43%, the school serves a relatively economically advantaged population. Jockey Hollow has earned 4-star ratings for three consecutive years, ranking 40th out of 258 Connecticut middle schools in 2025–2026 (84th percentile), 31st out of 252 in 2024–2025 (88th percentile), and 32nd out of 250 in 2023–2024 (87th percentile).

Academically, Jockey Hollow significantly outperforms the Connecticut state averages. In 2025–2026, English Language Arts proficiency across grades 6–8 ranged from 71.1% to 76.4%, compared to state averages of 51.1%–52.2% — a gap of 20 to 25 points. Math proficiency ranged from 56.6% to 68.4%, versus state averages of 41.9%–44.4% — a gap of 12 to 24 points. Eighth grade Science proficiency reached 72.8%, exceeding the state average of 50.9% by nearly 22 points. The school-wide chronic absenteeism rate of 7.0% is less than half the Connecticut state average of 16.4% and slightly better than the Monroe School District's 7.4%.

While performance is strong, a few trends deserve attention. Seventh grade Mathematics showed the largest improvement, jumping 6.8 points from 61.6% to 68.4%. Conversely, 6th grade ELA declined 5.6 points to 72.1%, and 8th grade ELA fell 3.9 points to 71.1%, suggesting a possible area for focus in literacy instruction. The Monroe School District ranks 56th out of 153 districts (63rd percentile, 3 stars), while Jockey Hollow itself ranks in the 84th percentile among middle schools — indicating the middle school is one of the district's stronger levels. Per-student spending of $17,263 (2018–2019) points to a well-funded school environment, though this figure is dated.