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B+
Schools in Chester · Chester School District, Regional School District 04

Chester’s public schools outscore 74% of Connecticut districts

68% of students in Chester’s public schools are proficient in reading, above the Connecticut average (50%). The grade covers the two public school districts serving Chester, from kindergarten through graduation, on state tests and graduation. Each state writes its own tests, so this is the one TownRatings grade compared within Connecticut, not nationally.

#40of 152 Connecticut townsK–12Where will my kid go?

From Connecticut state tests taken in spring 2022, when 96% of students in the tested grades sat them, and the class of 2023’s four-year graduation rate, as reported to the U.S. Department of Education.

Reading proficiency
68%
▲ 18 pts vs CT 50%
2021–22
Math proficiency
51%
▲ 11 pts vs CT 40%
2021–22
Graduate on time
95–100%
▲ 7–12 pts vs CT 88%
class of 2023
Spent per student
$32.5K
▲ 26% vs CT $25.9K
FY2024 · Regional School District 04
Students per teacher
9.7
CT 12.2 · smaller classes
Schools in town
1
824 students on the public path
In brief

Chester’s schools, in brief

Chester runs its own schools through grade 6, then shares

Chester Elementary School (PK–6) is Chester’s own. From grade 7, students attend the Regional School District 04 with Deep River and Essex: John Winthrop Middle School in Deep River, then Valley Regional High School in Deep River. The high school’s own results earn a B; the middle school earns a B−. See the path ↓

Above the state on both counts

Reading proficiency is 68% and math 51% across both districts in spring 2022, against 50% and 40% statewide; 95–100% of the class of 2023 graduated in four years, against 88%. Test scores ↓

Spending and class size

Chester spends $34,396 per student and Regional School District 04 $32,549, against $25,892 across Connecticut (FY2024). Neither counts toward the grade. Districts ↓

Written from the figures on this page. Tests are from 2021–22, graduation from the class of 2023; each school’s own letter uses 2020–21 results.

The School Grade

What’s behind Chester’s grade

B+ Test scoresA− Graduation

B+: better than 74% of Connecticut school districts, #40 of 152 Connecticut towns. Test scores and graduation are both above the Connecticut average; graduation is the stronger of the two.

Connecticut school districts we grade (199)Better than 74%
Lower resultsHigher results
Connecticut towns with similar household incomes (174)Better than 78%
BA−A fairly firm grade. Ordinary sampling error in 469 test results and a graduating class of 130 could put Chester anywhere from B to A−. The tests are from spring 2022, when 96% of Chester’s students in the tested grades sat them (469 in math, 470 in reading).

How TownRatings grades schools →

Where will my kid go?

Pick a grade. These are the public schools that serve Chester, with each school’s own grade.

The path, start to finish
PK–6Chester Elementary SchoolChester School DistrictA
7–8John Winthrop Middle Schoolin Deep RiverB−
9–12Valley Regional High Schoolin Deep RiverB

Chester runs its own schools through grade 6 (Chester School District). From grade 7, students attend the Regional School District 04, shared with Deep River and Essex. Its middle school is in Deep River. To confirm the school for a specific address, ask the district.

Two districts serve Chester

Spending and class size are shown but don’t count toward the grade. Each district’s own page has every school.

Chester School DistrictGrades PK–6 · 1 schools · 198 students, down 1% since 2020–21
$34,396CT $25,892 · FY2024
A+
Regional School District 04Grades 7–12 · 2 schools · 626 students, down 23% since 2020–21 · 9.7 per teacher (CT 12.2)
$32,549CT $25,892 · FY2024
B
Test scores · 2021–22

Well above the state in reading

Reading · PK–6, Chester School District72%
State average 50.5% · 109 students tested
Math · PK–6, Chester School District72%
State average 39.8% · 109 students tested
Reading · 7–12, Regional School District 0467%
State average 50.5% · 361 students tested
Math · 7–12, Regional School District 0445%
State average 39.8% · 360 students tested

Chester vs. its neighbors

Schools grades for the Connecticut towns that share Chester’s borders.

Schools next door
TownSchoolsMain districts
ChesterB+Chester PK–6 · Regional School District 04 7–12
Deep RiverA−Deep River PK–6 · Regional School District 04 7–12
LymeARegional School District 18
HaddamA−Regional School District 17
East HaddamBEast Haddam

Every school in Chester

3 schools. Each public school’s letter compares its own 2020–21 reading and math results with Connecticut’s other public schools (the newest school-level results we have).

District schools in Chesterby address
Chester Elementary School
Elementary · Grades PK–6
A
198 studentsRate it →
Also serving Chesterin other towns
John Winthrop Middle School
Middle · Grades 7–8 · Deep River
B−
197 students11:1Rate it →
Valley Regional High School
High · Grades 9–12 · Deep River
B
429 students9:1Rate it →

Questions about Chester’s schools

Are Chester’s schools good?

By Connecticut’s own tests, yes: the public schools Chester children attend outscore 74% of Connecticut’s school districts on tests and graduation, a B+ Schools grade, #40 of 152 Connecticut towns. Among towns with similar incomes they beat 78%. Tests are from 2021–22, graduation from the class of 2023.

What school district is Chester in?

Two districts: Chester School District runs grades PK–6, and Regional School District 04 runs grades 7–12, shared with Deep River and Essex.

Where do Chester kids go to high school?

Valley Regional High School in Deep River, with 429 students; its own test results earn a B.

What is Chester’s graduation rate?

95–100% of the class of 2023 in Regional School District 04 graduated in four years, against 88% across Connecticut.

How much does Chester spend per student?

$34,396 in Chester School District and $32,549 in Regional School District 04 (FY2024), against $25,892 across Connecticut. Spending doesn’t count toward the grade.

Parents talk

What Chester families are saying about school.

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Looking for colleges? Colleges near Chester → They have their own page.

School data: state test results (2021–22, with participation) and four-year graduation rates (class of 2023) reported to the U.S. Department of Education (EDFacts via ED Data Express); each school’s own letter uses its 2020–21 results (EDFacts via the Urban Institute); schools and enrollment from NCES (2024–25; private schools 2023–24); spending from the Census Bureau’s school finance survey (FY2024). The School Grade is our own summary, graded within Connecticut. Stars are from neighbors.