Each edition grades its towns against each other only.
Winchester grades D− overall, better than 2% of U.S. towns, mostly because of schools and incomes. Its public schools score at or near the bottom of New Hampshire. The median household income is $68K, and 14% of residents live below the poverty line. One bright spot: it has 60 miles of trail and 28% conserved land. History is its standout character grade: an A, better than 92% of U.S. towns, with 5 places on the National Register. 28% of the land in Winchester is conserved, where New Hampshire’s towns sit at 18% and U.S. towns at 4.3%. Only 5 of New Hampshire’s 187 towns score lower on health. Pisgah State Park, at 8,147 acres with 32.1 miles of trail, is the biggest park or preserve.
Where Winchester beats most towns, and one thing worth knowing.
Census counts: 1,209 in 1790, 4,150 in 2020. The archive holds 30 old photos and papers going back to 1896 and 5 maps from 1898 on.
5 places on the National Register of Historic Places.
Each subject compared with towns across the country (schools within New Hampshire), ordered by how far Winchester is from typical.
How TownRatings grades towns →
Who provides power, water and the rest in Winchester, 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 19, 2024.
Ordered by what stands out in Winchester.
Winchester sends many workers across the state line to Brattleboro and is safe by national standards but not by New Hampshire’s; it also carries more natural-hazard risk than most of New Hampshire (mostly inland flooding).
Each of its 3 graded neighbors has a higher School Grade than its D−, Richmond highest at C−.
Its public schools are run by the Winchester School District. Its one school is below.
| School | Level | Students | Letter |
|---|---|---|---|
| Winchester SchoolLargest public elementary schoolGrades PK–8 | Grades PK–8 | 322 | D− |
NCES · EDFacts · graded within NH on state tests
The typical Winchester home is worth about $300,000, up 2.2% in a year, 41% below the New Hampshire typical home.
| Winchester | New Hampshire towns | U.S. towns | |
|---|---|---|---|
| Households that own their home | 73% | 82% | 73% |
| Median rent | $1,209 a month | $1,393 a month | $1,185 a month |
Zillow Home Value Index · Redfin Data Center
FEMA rates its natural-hazard risk higher than 97% of New Hampshire towns, with expected losses of about $467 per resident a year; that rating is what its D for hazard risk is built on.
Winchester’s FEMA risk score is 84 of 100, above both New Hampshire’s towns (53 of 100) and U.S. towns (44 of 100). Since 1981, 13 flood insurance claims have been paid out in Winchester.
FEMA flood insurance claims · FEMA National Risk Index · OpenFEMA
60 miles of trail in 9 parks and preserves. Winchester’s trail density is 1.1 miles per square mile.
| Biggest places to walk | Trails | Acres |
|---|---|---|
| 1. Pisgah State Park | 32.1 mi | 8,147 |
| 2. Town Conservation Land | 1.2 mi | 170 |
| 3. Pauchaug Preserve | 0.9 mi | 137 |
Trails & parks © OpenStreetMap contributors · Conserved land: USGS PAD-US
33% of working residents cross a state line to work, Brattleboro among the top destinations. Jobs based here grew from 600 in 2013 to 833.
Since 2013, Winchester has added 233 jobs, to 833 in 2023. Only 10 of the 126 New Hampshire towns we compare have a lower median household income than Winchester. The average trip to work in Winchester is 29 minutes.
| Winchester | New Hampshire towns | U.S. towns | |
|---|---|---|---|
| Median household income | $68,000 | $103,000 | $80,000 |
| Average trip to work | 29 minutes | 28 minutes | 25 minutes |
Census LEHD 2023 · ACS
Winchester has cold, snowy winters and pleasant summers. July afternoons reach 83°, January nights drop to 14° and about 73 inches of snow falls in a winter.
NOAA U.S. Climate Normals, 1991–2020
16% of adults report frequent physical distress in Winchester. Among 126 New Hampshire towns, just 2 have a higher share of adults who say their health is fair or poor than Winchester. 31% of adults feel lonely in Winchester.
| Winchester | New Hampshire towns | U.S. towns | |
|---|---|---|---|
| Frequent physical distress (CDC PLACES) | 16% | 12% | 14% |
| Smoke cigarettes (CDC PLACES) | 16% | 11% | 14% |
| Yearly checkup (CDC PLACES) | 75% | 78% | 79% |
| Fair or poor health (CDC PLACES) | 21% | 14% | 19% |
| What stands out | Winchester | NH |
|---|---|---|
| More older adults who have lost all their teeth | 16.9% | 8.9% |
| More adults with COPD | 9.6% | 6.2% |
| More smokers | 16.4% | 10.8% |
CDC PLACES 2025 · modeled estimates for adults · CMS · HRSA
At 20 crimes per 1,000 residents a year, it reports more crime than 89% of New Hampshire’s graded towns. Reported crimes rose from 45 to 60 over the last three FBI years, a rise beyond ordinary year-to-year swings.
FBI crime data, 2025 · crimes reported to police
Museums, parks, gardens and other places to visit around Winchester. Close and well known come first.
15 mi MountainMount Monadnock
30 mi LakeQuabbin Reservoir
29 mi Ski areaMount Snow119 runs · 1,648 ft vertical
29 mi MuseumEmily Dickinson Museum
34 mi Ski areaStratton Mountain Resort106 runs · 1,899 ft vertical
37 mi MuseumMassachusetts Museum of Contemporary ArtMount Monadnock: Jonwmcinenrey, CC BY-SA 4.0 · Quabbin Reservoir: engineerchange, CC BY 2.0 · Mount Snow: William J Sisti from Morristown, NJ, USA, CC BY-SA 2.0 · Emily Dickinson Museum: Daderot, Public domain · Stratton Mountain Resort: Rudi Riet from Washington, DC, United States, CC BY-SA 2.0 · Massachusetts Museum of Contemporary Art: N-Lange.de, CC BY-SA 3.0
4 within 15 miles of the center of Winchester
About 2 of every 100 Winchester residents are enrolled in college, against 6 across New Hampshire.
Where Winchester’s working residents go each day. Line width shows the share.
Census LEHD 2023
5 places in Winchester on the National Register of Historic Places.
12 notable people were born in Winchester.
Town in New Hampshire, United States
Winchester is a town in Cheshire County, New Hampshire, United States. The population was 4,150 at the 2020 census. The primary community in the town, where 1,606 people resided at the 2020 census, is defined by the U.S. Census Bureau as the Winchester census-designated place (CDP). The town also includes the village of Ashuelot and part of Pisgah State Park.
From Wikipedia, licensed CC BY-SA 4.0 · facts via Wikidata (CC0)
4 towns share a border with Winchester.
| Town | NH rank | Overall | Cost | Safety | Schools | Health |
|---|---|---|---|---|---|---|
| Winchester | #125 | D− | C | B− | D− | C+ |
| Richmond | — | — | D | — | C− | C+ |
| Swanzey | #114 | C− | C− | B | C− | B+ |
| Hinsdale | #122 | D | B− | C− | D | B+ |
Richmond has fewer than 2,500 residents, so it gets subject grades but no overall grade. Richmond reports no FBI crime data of its own. Compare Winchester with a neighbor →
Short answers, built from the data on this page.
Winchester grades D− overall, better than 2% of U.S. towns. It grades C+ for health, B− for safety and D− for schools. Schools is its weak spot, with a D−.
New Hampshire has less crime than most states, so among its own towns Winchester sits nearer the middle.
The public schools Winchester children attend trail 100% of New Hampshire districts on state tests and graduation, a D− School Grade.
That is 3.6 years of the area's median household income ($83,329 across the Keene, NH 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.
12 notable people were born here, including Leonard Wood and Marshall Jewell.
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