Each edition grades its towns against each other only.
Cheshire is one of the best-graded places in America: an A+, 6th of 151 graded towns in Connecticut. It is healthier than 96% of U.S. towns, the median household earns $147K, and it reports less crime per resident than 90% of U.S. towns. The exception is cost of living: the typical home is worth about $535K, 6.2 years of the Waterbury metro’s $86K median household income. Cheshire’s trail density is 1.5 miles per square mile, close to Connecticut’s towns (1.3) and above U.S. towns (0.4). Cheshire has 3 places on the National Register of Historic Places, among them Farmington Canal Lock and First Congregational Church of Cheshire. Only 5 of the 90 Connecticut towns we compare have a lower violent crime rate than Cheshire.
Where Cheshire beats most towns.
Census counts: 2,230 in 1820, 28,733 in 2020. The archive holds 12 old photos and papers going back to 1879 and 2 maps from 1947 on.
3 places on the National Register of Historic Places.
Each subject compared with towns across the country (schools within Connecticut), ordered by how far Cheshire is from typical.
How TownRatings grades towns →
Museums, parks, gardens and other places to visit around Cheshire. Close and well known come first.
9 mi Theme parkLake Compounce
14 mi Stadium & arenaYale Bowl
21 mi Stadium & arenaPeoplesBank Arena
23 mi Stadium & arenaPratt & Whitney Stadium
29 mi LakeCandlewood Lake
7 mi Theme parkHoly Land USALake Compounce: Wildcat1 at English Wikipedia, Public domain · Yale Bowl: Kenneth Zirkel, CC BY-SA 4.0 · PeoplesBank Arena: PeoplesBank Arena, CC BY 2.5 · Pratt & Whitney Stadium: Quintin Soloviev, CC BY 4.0 · Candlewood Lake: Carol M. Highsmith, Public domain · Holy Land USA: Unknown authorUnknown author, Public domain
Who provides power, water and the rest in Cheshire, 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 Cheshire.
Cheshire trades workers with New Haven and other neighbors and has less food insecurity than most of Connecticut, but it has homes that cost more against local pay than most of Connecticut.
Its widest gap with Connecticut is food insecurity: 7.5% of its 22,852 adults worry about having enough food, against 14.9% statewide.
13% of Cheshire adults report frequent mental distress, below both the Connecticut town median (15%) and the median of U.S. towns (17%). 10% of Cheshire adults report frequent physical distress. Cheshire beats the Connecticut average on 18 of 32 CDC measures and trails it on 1.
| Cheshire | Connecticut towns | U.S. towns | |
|---|---|---|---|
| Frequent mental distress (CDC PLACES) | 13% | 15% | 17% |
| Frequent physical distress (CDC PLACES) | 10% | 12% | 14% |
| Smoke cigarettes (CDC PLACES) | 7.9% | 9.7% | 14% |
| Fair or poor health (CDC PLACES) | 11% | 14% | 19% |
| What stands out | Cheshire | CT |
|---|---|---|
| Fewer adults facing food insecurity | 7.5% | 14.9% |
| Fewer uninsured adults | 5.8% | 10% |
| More adults who have had cancer | 9.8% | 8.5% |
CDC PLACES 2025 · modeled estimates for adults · CMS · HRSA
Its A is the best School Grade on its borders; Southington (B+) is next. Its A for schools comes with a C− for cost of living: the typical home is worth about $535K.
Its public schools are run by the Cheshire School District. Three of its 8 schools are below, each with why it’s listed.
| School | Level | Students | Letter |
|---|---|---|---|
| Highland SchoolLargest public elementary schoolGrades K–6 | Grades K–6 | 899 | A+ |
| Cheshire High SchoolLargest public high schoolGrades 9–12 | Grades 9–12 | 1,208 | B+ |
| Chapman SchoolTop results in townGrades K–6 | Grades K–6 | 369 | A+ |
NCES · EDFacts · graded within CT on state tests and graduation
Reported crimes fell from 210 to 129 over the last three FBI years, a drop beyond ordinary year-to-year swings. Violent crime is rare: 2 reported in 2025, 0.1 per 1,000 residents.
The property crime rate in Cheshire is 4.1 per 1,000 residents.
FBI crime data, 2025 · crimes reported to police
49 miles of trail in 53 parks and preserves. The biggest place to walk is Yankee Expressway Highlands, 326 acres with 8.2 miles of trail.
| Biggest places to walk | Trails | Acres |
|---|---|---|
| 1. Yankee Expressway Highlands | 8.2 mi | 326 |
| 2. DeDominicis Property | 5.2 mi | 197 |
| 3. Ives Farm | 2.3 mi | 170 |
Trails & parks © OpenStreetMap contributors · Conserved land: USGS PAD-US
Cheshire has chilly, snowy winters and warm summers, with plenty of rain. July afternoons reach 84°, January nights drop to 19° and about 39 inches of snow falls in a winter.
NOAA U.S. Climate Normals, 1991–2020
At 6.2 years of the Waterbury metro’s $86K median household income, the typical home (about $535K) costs more against local pay than in 81% of Connecticut towns; that ratio is one input to its C− for cost of living.
87% of households own their home in Cheshire. The typical Cheshire home is worth about $535,000, up 4.1% in a year, 20% above the Connecticut typical home.
| Cheshire | Connecticut towns | U.S. towns | |
|---|---|---|---|
| Households that own their home | 87% | 81% | 73% |
| Median rent | $1,398 a month | $1,451 a month | $1,185 a month |
Census ACS, 2020–24 · Zillow Home Value Index · Redfin Data Center
Cheshire has about as many jobs (16,294) as working residents, but only 1,805 people both live and work here.
Most working residents leave Cheshire for work: only 13% work in town. Since 2013, Cheshire has added 1,818 jobs, to 16,294 in 2023. Cheshire’s average trip to work is 29 minutes.
| Cheshire | Connecticut towns | U.S. towns | |
|---|---|---|---|
| Median household income | $147,000 | $109,000 | $80,000 |
| Work from home | 19% | 15% | 11% |
| Average trip to work | 29 minutes | 27 minutes | 25 minutes |
| Below the poverty line | 5% | 5.8% | 9.6% |
Census LEHD 2023 · ACS
Expected storm and flood damage is higher than in 56% of U.S. communities. Since 1979, 32 flood insurance claims have been paid out in Cheshire.
FEMA flood insurance claims · FEMA National Risk Index · OpenFEMA
9 within 15 miles of the center of Cheshire
About 5 of every 100 Cheshire residents are enrolled in college, against 7 across Connecticut.
3 places in Cheshire on the National Register of Historic Places.
25 notable people were born in Cheshire.
City in Connecticut, United States
Cheshire ( CHEH-shurr), is a town in New Haven County, Connecticut, United States. At the time of the 2020 census, the population of Cheshire was 28,733. The town is part of the Naugatuck Valley Planning Region. The center of population of Connecticut is located in Cheshire.
From Wikipedia, licensed CC BY-SA 4.0 · facts via Wikidata (CC0)
8 towns share a border with Cheshire.
At #6 in CT, it grades higher overall than all 7 graded towns on its borders; Wolcott (A−) comes closest.
| Town | CT rank | Overall | Cost | Safety | Schools | Health |
|---|---|---|---|---|---|---|
| Cheshire | #6 | A+ | C− | A | A | A+ |
| Prospect | #70 | B+ | C− | — | B | A |
| Southington | #65 | B+ | C | B− | B+ | A |
| Meriden | #140 | D | D | C+ | C− | C+ |
| Wallingford | #53 | B+ | C− | A− | C+ | A |
| Waterbury | #150 | D− | D | C− | D | D |
| Hamden | #133 | C− | D | D | C− | A− |
| Wolcott | #46 | A− | D | A+ | B− | A |
Prospect reports no FBI crime data of its own. Compare Cheshire with a neighbor →
Short answers, built from the data on this page.
Yes, by almost any measure. Cheshire grades A+ overall, better than 96% of U.S. towns and #6 of 151 in Connecticut. It grades A+ for health, A for safety and A for schools. Cost of living is its weak spot, with a C−.
Yes. Cost of living, which also weighs rents, property taxes and how many households pay 30% or more of their income for housing, grades C−.
25 notable people were born here, including James Van Der Beek and John Frederick Kensett.
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