Each edition grades its towns against each other only.
The best of Chesterfield’s subject grades are an A for health and an A+ for history and the outdoors; the weakest is a C− for walkability. On walkability, just 29 of Massachusetts’ 325 towns do worse. 39% of the land in Chesterfield is conserved, above both Massachusetts’ towns (19%) and U.S. towns (4.3%). Its National Register listings include Gate Cemetery and Bisbee Mill. Chesterfield has fewer than 2,500 residents, so it gets subject grades but no overall grade.
Where Chesterfield beats most towns.
Bisbee Mill| Widest gap | Chesterfield | MA |
|---|---|---|
| Fewer older adults who have lost all their teeth | 5.5% | 11.9% |
Census counts: 1,183 in 1790, a low of 420 in 1930, 1,186 in 2020. The archive holds 6 old photos and papers going back to 1823 and 6 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 Chesterfield is from typical.
How TownRatings grades towns →
Museums, parks, gardens and other places to visit around Chesterfield. Close and well known come first.
23 mi National Historic SiteSpringfield Armory National Historic Site14K visitors a year
24 mi MountainMount Greylock
28 mi LakeQuabbin Reservoir
26 mi Theme parkSix Flags New England
24 mi TheatreTanglewood
26 mi MuseumNorman Rockwell MuseumSpringfield Armory National Historic Site: National Park Service, Public domain · Mount Greylock: Jstergis, CC BY 3.0 · Quabbin Reservoir: engineerchange, CC BY 2.0 · Six Flags New England: Canadaolympic989, Public domain · Tanglewood: Daderot., CC BY-SA 3.0 · Norman Rockwell Museum: User:Rmrfstar, CC BY 2.5
Who provides power, water and the rest in Chesterfield, 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 Chesterfield.
Chesterfield beats the Massachusetts average on 12 of 32 CDC measures and trails it on 2. 24% of Chesterfield adults have obesity, below both the Massachusetts town median (28%) and the median of U.S. towns (35%). 30% of Chesterfield adults sleep under 7 hours.
| Chesterfield | Massachusetts towns | U.S. towns | |
|---|---|---|---|
| Obesity (CDC PLACES) | 24% | 28% | 35% |
| Sleep under 7 hours (CDC PLACES) | 30% | 33% | 36% |
| Frequent mental distress (CDC PLACES) | 14% | 16% | 17% |
| Yearly checkup (CDC PLACES) | 84% | 82% | 79% |
| What stands out | Chesterfield | MA |
|---|---|---|
| Fewer older adults who have lost all their teeth | 5.5% | 11.9% |
| Fewer adults facing food insecurity | 7.1% | 12.4% |
| More adults who have had cancer | 11.6% | 8.5% |
CDC PLACES 2025 · modeled estimates for adults · CMS · HRSA
Its public schools are run by the Chesterfield-Goshen school district. Its one school is below.
| School | Level | Students | Letter |
|---|---|---|---|
| New Hingham Regional ElementaryLargest public elementary schoolGrades PK–6 | Grades PK–6 | 126 | B− |
NCES · EDFacts · graded within MA on state tests and graduation
16 miles of trail in 12 parks and preserves. Chesterfield’s trail density is 0.5 miles per square mile. The biggest park or preserve is Gilbert A. Bliss State Forest, at 626 acres.
| Biggest places to walk | Trails | Acres |
|---|---|---|
| 1. Dead Branch State Forest | 1.8 mi | 577 |
| 2. Brewer Brook Wildlife Management Area | 1.2 mi | 172 |
| 3. Chesterfield Gorge Reservation | 1 mi | 200 |
Trails & parks © OpenStreetMap contributors · Conserved land: USGS PAD-US
The typical Chesterfield home is worth about $399,000, up 1% in a year, 39% below the Massachusetts typical home. 92% of households own their home in Chesterfield.
| Chesterfield | Massachusetts towns | U.S. towns | |
|---|---|---|---|
| Households that own their home | 92% | 79% | 73% |
| Median rent | $1,078 a month | $1,683 a month | $1,185 a month |
Census ACS, 2020–24 · Zillow Home Value Index · Redfin Data Center
No town among the 284 in Massachusetts we compare has a lower share of working residents who work in town than Chesterfield. Since 2013, Chesterfield has added 36 jobs, to 137 in 2023. The average trip to work in Chesterfield is 31 minutes.
| Chesterfield | Massachusetts towns | U.S. towns | |
|---|---|---|---|
| Working residents who work in town | 1.1% | 9.8% | 8% |
| Average trip to work | 31 minutes | 30 minutes | 25 minutes |
| Median household income | $104,000 | $120,000 | $80,000 |
| Below the poverty line | 6.4% | 6% | 9.6% |
Census LEHD 2023 · ACS
Chesterfield has cold, snowy winters and pleasant summers, with plenty of rain. July afternoons reach 81°, January nights drop to 14° and about 77 inches of snow falls in a winter.
NOAA U.S. Climate Normals, 1991–2020
Among 278 Massachusetts towns, just 6 have a lower violent crime rate than Chesterfield. Chesterfield's reported crime rate is well below Massachusetts's. Most reported incidents are property crimes, mainly thefts.
| Chesterfield | Massachusetts towns | U.S. towns | |
|---|---|---|---|
| Violent crimes per 1,000 (2025) | 0 per 1,000 residents | 1.5 | 1.6 |
| Property crimes per 1,000 (2025) | 0.9 per 1,000 residents | 4.9 | 9.9 |
FBI crime data, 2025 · crimes reported to police
Expected storm and flood damage is higher than in 58% of U.S. communities. Since 2014, 2 flood insurance claims have been paid out in Chesterfield.
FEMA flood insurance claims · FEMA National Risk Index · OpenFEMA
2 within 15 miles of the center of Chesterfield
About 3 of every 100 Chesterfield residents are enrolled in college, against 8 across Massachusetts.
In a town this size, neighbors are the best guide. Ask them anything.
5 places in Chesterfield on the National Register of Historic Places.
3 notable people were born in Chesterfield.
Town in Massachusetts, United States
Chesterfield is a rural hill town in Hampshire County, Massachusetts, United States, 26 miles (42 km) east of Pittsfield, 75 miles (120 km) west of Worcester, and 90 miles (140 km) west of Boston. The population was 1,186 at the 2020 census. It is part of the Springfield, Massachusetts Metropolitan Statistical Area.
From Wikipedia, licensed CC BY-SA 4.0 · facts via Wikidata (CC0)
Short answers, built from the data on this page.
That is 4.6 years of the area's median household income ($87,001 across the Amherst Town-Northampton, 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 Elijah H. Mills and William L. Higgins.
,_Tanglewood,_Lenox,_Massachusetts.JPG){kind=link}
