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Cheshire, Massachusetts

Cheshire is a small town of about 3,200 people in Berkshire County, Massachusetts. It has lost about 2% of its people since 2020. A typical home costs about 3.8 years of the typical household's income, compared with 4.1 across the U.S. The nearest metro area of about a million people or more, Hartford, is about 60 miles away as the crow flies.

Population
3,180
down 2.1% since 2020
Typical home, 2020-24
$268,200
Berkshire County prices up 23% since 2022
Household income
$69,803
U.S.: $80,734
Prices, Pittsfield area
95.1
U.S. average = 100
Emergency room
9 miles
Pittsfield, MA
To Hartford
60 mi
straight line

The book's checklist

  • Lower cost of livingEveryday prices run 4.9% below the U.S. average in the Pittsfield metro area.
  • More house for the moneyA typical home costs 3.8 years of the typical household's income here. Across the U.S. it's 4.1.
  • A safer neighborhood1 violent crime was reported in 2025, about 0.3 per 1,000 people (U.S.: 3.3). Property crime: 2.5 per 1,000 (U.S.: 15.3).
  • Schools in town2 public schools: 1 middle and 1 high school.
  • A hospital close byBerkshire Medical Center in Pittsfield, about 9 miles away, has the nearest emergency room.
  • Within reach of a big cityHartford is about 60 miles away as the crow flies. The book suggests staying within about 60 miles if you'll miss big-city sports, concerts and theater.

A check means Cheshire meets the rule of thumb from Frank and Dave's book. An empty box isn't a deal breaker: it's something to weigh for your family. A question mark means there isn't enough data.

For a lifetime

Homes and money

Typical home value, as owners valued them in 2020-2024
$268,200U.S.: $332,700
Home prices since then
Up 23%Berkshire County, 2022 to 2025
Typical household income
$69,803U.S.: $80,734
Homes owned by the people living in them
89%U.S.: 65%
Typical property tax bill
$3,005 a yearMassachusetts: $5,992
Homes built before 1940
30%U.S.: 12%
Homes built since 2010
3%U.S.: 11%
Vacation and seasonal homes
6%U.S.: 3%
Everyday prices
95.1U.S. average = 100 (the Pittsfield metro area)

Home values and rents are what households told the Census Bureau across 2020 to 2024, so they trail today's market: county prices have moved up 23% since 2022. Everyday prices are the government's average for the Pittsfield metro area, not Cheshire alone. Check current listings before you budget.

Sources: U.S. Census Bureau, American Community Survey 2020-2024 5-year estimates; Federal Housing Finance Agency, House Price Index for counties (all transactions); U.S. Bureau of Economic Analysis, Regional Price Parities, 2024.

The people

Population, 2025 estimate
3,1802020: 3,249
Median age
53.7 yearsU.S.: 38.9
Age 65 and older
31%U.S.: 17%
Under 18
15%U.S.: 22%
Adults with a bachelor's degree or more
27%U.S.: 36%
Moved here from another county or state in the past year
2%U.S.: 6%
College students
5%share of all residents

Sources: U.S. Census Bureau, Population Estimates (Vintage 2025); U.S. Census Bureau, American Community Survey 2020-2024 5-year estimates.

Work

Biggest lines of work
Schools, health care and social services (30%); retail (15%); transportation, warehousing and utilities (9%)
Unemployment rate
5%U.S.: 5%
Average commute
29 minutesU.S.: 26 minutes
Work from home
4%U.S.: 15%
Below the poverty line
9%U.S.: 12%

Sources: U.S. Census Bureau, American Community Survey 2020-2024 5-year estimates.

Health care

Nearest emergency room: Berkshire Medical Center, Pittsfield, MA, about 9 miles away. It's a general hospital. Medicare gives it 4 of 5 stars.

Look up doctors, clinics and the hospitals themselves on Medicare's Care Compare. Ask where the most serious cases are sent.

Sources: Centers for Medicare & Medicaid Services, Hospital General Information.

Schools

2 public schools in Cheshire, run by Hoosac Valley Regional.

See each school on the federal school search, then check test scores and graduation rates on Massachusetts's school report card.

Sources: National Center for Education Statistics, Common Core of Data, 2023-24 (via the Urban Institute Education Data Portal); National Center for Education Statistics, IPEDS institution directory, 2024.

Internet

Homes with cable, fiber or DSL internet
78%U.S.: 76%
Homes with any internet subscription
86%U.S.: 91%

Before you buy, look up the address on the FCC's National Broadband Map to see which providers serve it.

Sources: U.S. Census Bureau, American Community Survey 2020-2024 5-year estimates.

Weather

January average low
14°F
July average high
81°F
Days 90°F or hotter
4 a year
Nights at or below freezing
149 a year
Rain and melted snow
49.6 inches a year
Snow
85 inches a year
Elevation
953 feet

Weather stations: North Adams Harriman Ap (9 miles away) and Ashfield (16 miles away, rain and snow). Averages for 1991 to 2020.

Sources: NOAA National Centers for Environmental Information, U.S. Climate Normals 1991-2020; U.S. Geological Survey, 3D Elevation Program.

Getting around

Straight-line miles. The road is always longer, and as the book says, an interstate at 70 is a different trip from a farm road at 45. Check the real drive: Berkshire Medical Center, Troy, Hartford.

Berkshire County is in a metro area of fewer than 250,000 people (USDA rural-urban code 3, on a scale where 1 is the biggest metro areas and 9 the most rural counties).

For a day

4 places on the National Register of Historic Places, including the Cheshire Town Hall Complex and the Farnams Village Historic District.

National Park Service sites within about an hour:

  • Appalachian National Scenic Trailright here
  • Martin Van Buren National Historic Site31 miles
  • Saratoga National Historical Park37 miles
  • New England National Scenic Trail40 miles
  • Springfield Armory National Historic Site43 miles

Read about Cheshire's history on Wikipedia.

Know Cheshire?

Tell us what a visitor shouldn't miss, and what living there is really like. Write to Main Street at mainstreet@smalltownguide.com. The best notes from people who know the town will be added here.

Nearby

Straight-line miles.

Small towns

Smaller places

  • New Ashford, MA246 people, 5 miles
  • Windsor, MA817 people, 6 miles
  • Savoy, MA655 people, 7 miles
  • Hancock, MA748 people, 9 miles
  • Florida, MA700 people, 10 miles
  • Plainfield, MA643 people, 12 miles
  • Peru, MA791 people, 12 miles
  • Hawley, MA350 people, 13 miles

Sources

  1. U.S. Census Bureau, Population Estimates (Vintage 2025)
  2. U.S. Census Bureau, American Community Survey 2020-2024 5-year estimates
  3. Federal Housing Finance Agency, House Price Index for counties (all transactions)
  4. U.S. Bureau of Economic Analysis, Regional Price Parities, 2024
  5. FBI, Crime in the United States, Table 8 (offenses known to law enforcement by city)
  6. Centers for Medicare & Medicaid Services, Hospital General Information
  7. National Center for Education Statistics, Common Core of Data, 2023-24 (via the Urban Institute Education Data Portal)
  8. National Center for Education Statistics, IPEDS institution directory, 2024
  9. NOAA National Centers for Environmental Information, U.S. Climate Normals 1991-2020
  10. U.S. Geological Survey, 3D Elevation Program
  11. National Park Service, National Register of Historic Places listings
  12. National Park Service, park unit boundaries
  13. USDA Economic Research Service, Rural-Urban Continuum Codes, 2023
  14. U.S. Census Bureau, 2025 Gazetteer files and 2020 urban areas

Census survey figures are estimates with a margin of error; we leave out any figure whose margin is too wide to be useful. Data last gathered October 5, 2026. See something wrong? Write to mainstreet@smalltownguide.com.