Each edition grades its towns against each other only.
Cheshire's standout: it has 23 miles of trail and 39% conserved land. Overall it grades B−, ranked 196th of 282 in Massachusetts. It reports less crime per resident than 95% of U.S. towns and it is easier to get around on foot or by transit than 87% of U.S. towns. Its weakest subject is schools: its schools rank behind 84% of the state's. History is its standout character grade: an A+, better than 96% of U.S. towns, with 5 places on the National Register. 39% of the land in Cheshire is conserved, against 19% in Massachusetts’ towns and 4.3% across U.S. towns. On hazard risk, just 12 of Massachusetts’ 325 towns do worse. Chalet Wildlife Management Area, at 2,423 acres with 1.7 miles of trail, is the biggest park or preserve.
Where Cheshire beats most towns.
Hall's Tavern
Census counts: 1,298 in 1850, a low of 1,221 in 1900, 3,258 in 2020. The archive holds 6 old photos and papers going back to 1898 and 7 maps from 1886 on.
5 places on the National Register of Historic Places.
Each subject compared with towns across the country (schools within Massachusetts), 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.
5 mi MountainMount Greylock
10 mi MuseumClark Art Institute
17 mi TheatreTanglewood
22 mi MuseumNorman Rockwell Museum
9 mi MuseumMassachusetts Museum of Contemporary Art
31 mi Stadium & arenaMVP ArenaMount Greylock: Jstergis, CC BY 3.0 · Clark Art Institute: Daderot, Public domain · Tanglewood: Daderot., CC BY-SA 3.0 · Norman Rockwell Museum: User:Rmrfstar, CC BY 2.5 · Massachusetts Museum of Contemporary Art: N-Lange.de, CC BY-SA 3.0 · MVP Arena: This image or media was taken or created by Matt H. Wade. To see his entire port, CC BY-SA 3.0
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 Nov 18, 2024.
Ordered by what stands out in Cheshire.
Cheshire keeps more of its land conserved than most of Massachusetts and is healthier than towns with similar incomes, but it carries more natural-hazard risk than most of Massachusetts (mostly inland flooding).
Violent crime is rare: 1 reported in 2025, 0.3 per 1,000 residents.
Cheshire’s violent crime rate is 0.3 per 1,000 residents, where Massachusetts’ towns sit at 1.5 and U.S. towns at 1.6. Cheshire’s property crime rate is 2.5 per 1,000 residents.
| Cheshire | Massachusetts towns | U.S. towns | |
|---|---|---|---|
| Violent crimes per 1,000 (2025) | 0.3 per 1,000 residents | 1.5 | 1.6 |
| Property crimes per 1,000 (2025) | 2.5 per 1,000 residents | 4.9 | 9.9 |
FBI crime data, 2025 · crimes reported to police
Its public schools are run by the Hoosac Valley Regional school district. Its two schools are below.
| School | Level | Students | Letter |
|---|---|---|---|
| Hoosac Valley Middle SchoolLargest public middle schoolGrades 4–7 | Grades 4–7 | 304 | D |
| Hoosac Valley High SchoolLargest public high schoolGrades 8–12 | Grades 8–12 | 296 | C |
NCES · EDFacts · graded within MA on state tests and graduation
Its 6,779 conserved acres are a larger share of the town than in 93% of Massachusetts towns.
23 miles of trail in 8 parks and preserves. The trail density in Cheshire is 0.9 miles per square mile.
| Biggest places to walk | Trails | Acres |
|---|---|---|
| 1. Mount Greylock State Reservation | 9.9 mi | 1,542 |
| 2. Appalachian Trail Corridor | 3.4 mi | 327 |
| 3. Cheshire Water Company Land | 3.2 mi | 641 |
Trails & parks © OpenStreetMap contributors · Conserved land: USGS PAD-US
The typical Cheshire home is worth about $360,000, up 1.8% in a year, 45% below the Massachusetts typical home. 89% of Cheshire households own their home.
Census ACS, 2020–24 · Zillow Home Value Index · Redfin Data Center
Most working residents leave Cheshire for work: only 8% work in town. The top destinations are Pittsfield (33%), Adams (9%) and North Adams (7%). Half commute less than 10 miles.
| Cheshire | Massachusetts towns | U.S. towns | |
|---|---|---|---|
| Median household income | $70,000 | $120,000 | $80,000 |
| Average trip to work | 29 minutes | 30 minutes | 25 minutes |
| Below the poverty line | 8.6% | 6% | 9.6% |
Census LEHD 2023 · ACS
FEMA rates its natural-hazard risk higher than 97% of Massachusetts towns, with expected losses of about $349 per resident a year; that rating is what its C− for hazard risk is built on.
Among 283 Massachusetts towns, just 9 have a higher FEMA risk score than Cheshire. Since 1979, 11 flood insurance claims have been paid out in Cheshire.
FEMA flood insurance claims · FEMA National Risk Index · OpenFEMA
Against the 10,501 U.S. towns with household incomes like Cheshire’s, it is healthier than 86%, so its B+ isn’t only a matter of income. Within Massachusetts it is less healthy than 80% of the 279 graded towns: Massachusetts sets a high bar.
Cheshire beats the Massachusetts average on 3 of 32 CDC measures and trails it on 7. 37% of adults sleep under 7 hours in Cheshire.
| Cheshire | Massachusetts towns | U.S. towns | |
|---|---|---|---|
| Sleep under 7 hours (CDC PLACES) | 37% | 33% | 36% |
| Depression (CDC PLACES) | 26% | 24% | 23% |
| Obesity (CDC PLACES) | 31% | 28% | 35% |
| Frequent physical distress (CDC PLACES) | 14% | 12% | 14% |
| What stands out | Cheshire | MA |
|---|---|---|
| Fewer adults facing housing insecurity | 8.9% | 11.1% |
| More adults screened for colon cancer | 73.6% | 68.4% |
| More adults with heart disease | 7.7% | 5.8% |
CDC PLACES 2025 · modeled estimates for adults · CMS · HRSA
Cheshire has cold, snowy winters and pleasant summers. July afternoons reach 81°, January nights drop to 13° and about 77 inches of snow falls in a winter.
NOAA U.S. Climate Normals, 1991–2020
3 within 15 miles of the center of Cheshire
About 5 of every 100 Cheshire residents are enrolled in college, against 8 across Massachusetts.
Where Cheshire’s working residents go each day. Line width shows the share.
Census LEHD 2023
5 places in Cheshire on the National Register of Historic Places.
3 notable people were born in Cheshire.
Town in Massachusetts, United States
Cheshire is a town in Berkshire County, Massachusetts, United States. It is part of the Pittsfield, Massachusetts Metropolitan Statistical Area. The population was 3,258 at the 2020 census. It contains the census-designated place of the same name.
From Wikipedia, licensed CC BY-SA 4.0 · facts via Wikidata (CC0)
5 towns share a border with Cheshire.
| Town | MA rank | Overall | Cost | Safety | Schools | Health |
|---|---|---|---|---|---|---|
| Cheshire | #196 | B− | C | A+ | C− | B+ |
| Lanesborough | #127 | B+ | C | — | A− | B+ |
| New Ashford | — | — | — | — | — | — |
| Windsor | — | — | — | — | — | — |
| Savoy | — | — | — | — | — | — |
| Dalton | #173 | B | C+ | A− | B− | A− |
Lanesborough reports no FBI crime data of its own. New Ashford, Windsor and Savoy aren’t graded (fewer than 1,000 residents, or not enough data). Compare Cheshire with a neighbor →
Short answers, built from the data on this page.
Cheshire grades B− overall, better than 51% of U.S. towns and #196 of 282 in Massachusetts. It grades B+ for health, A+ for safety and C− for schools. Schools is its weak spot, with a C−.
That is 4.7 years of the area's median household income ($76,013 across the Pittsfield, MA metro area). Cost of living, which also weighs rents, property taxes and how many households pay 30% or more of their income for housing, grades C.
3 notable people were born here, including Horace Smith and Almon W. Babbitt.
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