Each edition grades its towns against each other only.
For most people who can afford it, yes. Chester grades B overall, ranked 86th of 151 in Connecticut. Residents are healthier than 80% of U.S. towns on CDC estimates. The trade-off is money: homes are expensive, about $540K for a typical one and 5.7 times the Hartford metro’s $95K median household income. 36% of the land in Chester is conserved, above both the Connecticut town median (14%) and the median of U.S. towns (4.3%). The biggest place to walk is Cockaponset State Forest, 3,707 acres with 41.5 miles of trail. Chester is easier to get around on foot or by transit than 79% of U.S. towns.
Where Chester beats most towns.
Census counts: 974 in 1840, 3,749 in 2020. The archive holds 18 old photos and papers going back to 1793 and 5 maps from 1893 on.
5 places on the National Register of Historic Places.
Each subject compared with towns across the country (schools within Connecticut), ordered by how far Chester is from typical.
How TownRatings grades towns →
Museums, parks, gardens and other places to visit around Chester. Close and well known come first.
3 mi State parkGillette Castle State Park
26 mi Stadium & arenaYale Bowl
21 mi Stadium & arenaMohegan Sun Arena
27 mi Stadium & arenaPeoplesBank Arena
28 mi Theme parkLake Compounce
25 mi Stadium & arenaPratt & Whitney StadiumGillette Castle State Park: Original uploader was Kevinpepin at en.wikipedia, Public domain · Yale Bowl: Kenneth Zirkel, CC BY-SA 4.0 · Mohegan Sun Arena: Bbjeter, CC BY-SA 3.0 · PeoplesBank Arena: PeoplesBank Arena, CC BY 2.5 · Lake Compounce: Wildcat1 at English Wikipedia, Public domain · Pratt & Whitney Stadium: Quintin Soloviev, CC BY 4.0
Who provides power, water and the rest in Chester, and how to reach them.
EPA SDWIS (Oct 9, 2026) · HIFLD + EIA-861 2025 · Census 2020 ZCTAs · NCES 2024–25 · registration: vote.gov, updated Sep 30, 2026.
Ordered by what stands out in Chester.
Chester keeps more of its land conserved than most of Connecticut, trades workers with Essex and other neighbors and is healthy by national standards but behind most towns in Connecticut.
Its 3,837 conserved acres are a larger share of the town than in 96% of Connecticut towns.
48 miles of trail in 13 parks and preserves. Chester’s trail density is 2.9 miles per square mile, above both Connecticut’s towns (1.3) and U.S. towns (0.4).
| Biggest places to walk | Trails | Acres |
|---|---|---|
| 1. Cockaponset State Forest | 41.5 mi | 3,707 |
| 2. Constance Baker Motley Preserve | 0.4 mi | 6 |
| 3. Chester Creek Preserve | — | 42 |
Trails & parks © OpenStreetMap contributors · Conserved land: USGS PAD-US
Its public schools are run by the Chester School District. Its one school is below.
| School | Level | Students | Letter |
|---|---|---|---|
| Chester Elementary SchoolLargest public elementary schoolGrades PK–6 | Grades PK–6 | 198 | A |
NCES · EDFacts · graded within CT on state tests and graduation
Within Connecticut it is less healthy than 71% of the 154 graded towns: Connecticut sets a high bar. All 4 graded neighbors score healthier than its A−, from East Haddam (A) to Haddam (A+).
27% of adults feel lonely in Chester. Chester beats the Connecticut average on 11 of 32 CDC measures and trails it on 7. 15% of adults report frequent mental distress in Chester.
| Chester | Connecticut towns | U.S. towns | |
|---|---|---|---|
| Feel lonely (CDC PLACES) | 27% | 31% | 33% |
| Yearly checkup (CDC PLACES) | 84% | 81% | 79% |
| High blood pressure (CDC PLACES) | 38% | 33% | 35% |
| Sleep under 7 hours (CDC PLACES) | 32% | 34% | 36% |
| What stands out | Chester | CT |
|---|---|---|
| Fewer uninsured adults | 5.9% | 10% |
| Fewer adults facing food insecurity | 8.9% | 14.9% |
| More adults who have had cancer | 11.7% | 8.5% |
CDC PLACES 2025 · modeled estimates for adults · CMS · HRSA
People 65 and older are 27% of residents (19% statewide); adults 18 to 34 are 17% of residents (22% statewide). The median age in Chester is 54 years. 48% of adults 25 and older have a bachelor’s degree or more, vs 43% across Connecticut.
| Chester | Connecticut towns | U.S. towns | |
|---|---|---|---|
| Median age | 54 years | 44.4 years | 40.5 years |
| Aged 65 or older | 27% | 20% | 18% |
| Bachelor’s degree or more, 25+ | 48% | 45% | 29% |
| Under 18 | 18% | 19% | 22% |
45% women, 55% men
About 120 men for every 100 women (the survey’s margin: ±3.4 points). Across Connecticut, 50.9% of residents are women.
| Chester | CT | U.S. | |
|---|---|---|---|
| Under 10 | 12.4% | 10.4% | 11.6% |
| 10 to 17 | 5.1% | 9.8% | 10.3% |
| 18 to 24 | 8.5% | 9.3% | 9.1% |
| 25 to 34 | 8.1% | 12.6% | 13.7% |
| 35 to 44 | 10% | 12.7% | 13.2% |
| 45 to 54 | 7.1% | 12.5% | 12.2% |
| 55 to 64 | 21.9% | 14.2% | 12.7% |
| 65 to 74 | 17.1% | 10.7% | 10.2% |
| 75 and older | 9.8% | 7.8% | 7% |
| No diploma | 3.3% | 8.5% | 10.4% |
| High school | 18.7% | 25.3% | 26% |
| Some college | 22.5% | 16.1% | 19.1% |
| Associate’s | 7.6% | 7.6% | 8.8% |
| Bachelor’s | 22.3% | 23.3% | 21.6% |
| Graduate | 25.5% | 19.2% | 14.1% |
U.S. Census Bureau · ACS 2020-2024 5-year estimates · in a town of 3,700, single groups can be off by several points
Chester has chilly winters and pleasant summers, with plenty of rain. July afternoons reach 83°, January nights drop to 20° and about 28 inches of snow falls in a winter.
NOAA U.S. Climate Normals, 1991–2020
Typical home values rose 5.7% in the year to September 2026. Chester’s median rent is $1,549 a month.
| Chester | Connecticut towns | U.S. towns | |
|---|---|---|---|
| Median rent | $1,549 a month | $1,448 a month | $1,185 a month |
| Households that own their home | 73% | 81% | 73% |
Census ACS, 2020–24 · Zillow Home Value Index · Redfin Data Center
Chester has about as many jobs (1,840) as working residents, but only 195 people both live and work here.
Most working residents leave Chester for work: only 11% work in town. 12% of Chester residents live below the poverty line. The top destinations are Essex (7%), Hartford (5%) and Middletown (5%).
| Chester | Connecticut towns | U.S. towns | |
|---|---|---|---|
| Work from home | 18% | 15% | 11% |
| Below the poverty line | 12% | 5.8% | 9.6% |
| Median household income | $109,000 | $109,000 | $80,000 |
| Average trip to work | 28 minutes | 27 minutes | 25 minutes |
Census LEHD 2023 · ACS
Expected storm and flood damage is higher than in 64% of U.S. communities. Since 1982, 34 flood insurance claims have been paid out in Chester.
FEMA flood insurance claims · FEMA National Risk Index · OpenFEMA
1 within 15 miles of the center of Chester
About 4 of every 100 Chester residents are enrolled in college, against 7 across Connecticut.
35.8% of the town is conserved land, across 13 parks and preserves.
5 places in Chester on the National Register of Historic Places.
3 notable people were born in Chester.
Town in Connecticut, United States
Chester is a town in Middlesex County, Connecticut, United States. The town is part of the Lower Connecticut River Valley Planning Region. The population was 3,749 at the 2020 census. The town center is defined by the U.S. Census Bureau as a census-designated place (CDP). The name is a transfer from Chester, in England.
From Wikipedia, licensed CC BY-SA 4.0 · facts via Wikidata (CC0)
6 towns share a border with Chester.
All 3 graded towns on its borders grade higher than its B; Haddam (B+) is closest.
| Town | CT rank | Overall | Cost | Safety | Schools | Health |
|---|---|---|---|---|---|---|
| Chester | #86 | B | D | — | B+ | A− |
| Deep River | #33 | A− | C | — | A− | A |
| Deep River Center | — | — | — | — | — | — |
| Chester Center | — | — | — | — | — | — |
| Lyme | — | — | C− | — | A | A |
| Haddam | #62 | B+ | D | — | A− | A+ |
| East Haddam | #49 | A− | C+ | — | B | A |
Lyme has fewer than 2,500 residents, so it gets subject grades but no overall grade. Chester, Deep River, Lyme, Haddam and East Haddam report no FBI crime data of their own. Deep River Center and Chester Center aren’t graded (fewer than 1,000 residents, or not enough data). Compare Chester with a neighbor →
Short answers, built from the data on this page.
For most people who can afford it, yes. Chester grades B overall, better than 59% of U.S. towns and #86 of 151 in Connecticut. It grades A− for health and B+ for schools. Cost of living is its weak spot, with a D.
Yes. Cost of living, which also weighs rents, property taxes and how many households pay 30% or more of their income for housing, grades D.
3 notable people were born here, including Paul Hopkins and William Davis Shipman.
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