Each edition grades its towns against each other only.
Winchester is a solid, middle-of-the-road choice. It grades B− overall, 93rd among Connecticut's 151 graded towns, with no subject far below average. Its best mark is health: CDC estimates put its residents' health ahead of 70% of the country. It also does better than most on safety: crime is low: it reports less per resident than 69% of U.S. towns. Its lowest everyday mark is in cost of living: the typical home is worth about $397K, 4.2 years of the Torrington area’s $94K median household income. History is its standout character grade: an A, better than 94% of U.S. towns, with 9 places on the National Register. On hazard risk, just 2 of Connecticut’s 175 towns do worse. Winchester is easier to get around on foot or by transit than 86% of U.S. towns. Its National Register listings include Solomon Rockwell House and Winsted Green Historic District.
Where Winchester beats most towns.
Census counts: 1,601 in 1820, 10,224 in 2020. The archive holds 11 old photos and papers going back to 2008 and 3 maps from 1892 on.
9 places on the National Register of Historic Places.
Winchester takes its name from Winchester in Hampshire, England, 3,330 miles across the Atlantic.
UKUK editionWinchester, settled in 1771, takes its name from Winchester, a large town in Hampshire, England.
Named after: each U.S. town’s Wikipedia article. Grades compare each town with towns in its own country, so they aren’t a head-to-head.
Each subject compared with towns across the country (schools within Connecticut), 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 Sep 30, 2026.
Ordered by what stands out in Winchester.
Winchester is healthier than towns with similar incomes and is safe by national standards but not by Connecticut’s.
Winchester’s FEMA risk score is 80 of 100, above both Connecticut’s towns (56 of 100) and U.S. towns (44 of 100). Since 1978, 5 flood insurance claims have been paid out in Winchester.
FEMA flood insurance claims · FEMA National Risk Index · OpenFEMA
Two of its 6 schools are below, each with why it’s listed. The largest public high school is Northwestern Regional High School, with 536 students.
| School | Level | Students | Letter |
|---|---|---|---|
| Pearson SchoolLargest public elementary schoolGrades 2–6 | Grades 2–6 | 318 | B− |
| Northwestern Regional High SchoolLargest public high schoolGrades 9–12 | Grades 9–12 | 536 | A− |
NCES · EDFacts · graded within CT on state tests
Most working residents leave Winchester for work: only 10% work in town. Winchester’s median household income is $67,000, where Connecticut’s towns sit at $109,000 and U.S. towns at $80,000. 13% of Winchester residents live below the poverty line.
| Winchester | Connecticut towns | U.S. towns | |
|---|---|---|---|
| Work from home | 6.9% | 16% | 11% |
| Median household income | $67,000 | $109,000 | $80,000 |
| Below the poverty line | 13% | 5.8% | 9.6% |
Census LEHD 2023 · ACS
Against the 10,144 U.S. towns with household incomes like Winchester’s, it is healthier than 90%, so its B+ isn’t only a matter of income. Within Connecticut it is less healthy than 78% of the 154 graded towns: Connecticut sets a high bar.
14% of adults report frequent physical distress in Winchester. Winchester beats the Connecticut average on 5 of 32 CDC measures and trails it on 6. 29% of adults have obesity in Winchester.
| Winchester | Connecticut towns | U.S. towns | |
|---|---|---|---|
| Frequent physical distress (CDC PLACES) | 14% | 12% | 14% |
| Obesity (CDC PLACES) | 29% | 30% | 35% |
| Smoke cigarettes (CDC PLACES) | 13% | 9.7% | 14% |
| Sleep under 7 hours (CDC PLACES) | 33% | 34% | 36% |
| What stands out | Winchester | CT |
|---|---|---|
| Fewer uninsured adults | 7.7% | 10% |
| Fewer adults facing housing insecurity | 9.9% | 12.5% |
| More adults with COPD | 7.1% | 5.6% |
CDC PLACES 2025 · modeled estimates for adults · CMS · HRSA
At 11.5 crimes per 1,000 residents a year, it reports less crime than 57% of Connecticut’s graded towns.
Among 90 Connecticut towns, just 7 have a higher violent crime rate than Winchester.
| Winchester | Connecticut towns | U.S. towns | |
|---|---|---|---|
| Violent crimes per 1,000 (2025) | 1.6 per 1,000 residents | 0.4 | 1.6 |
| Property crimes per 1,000 (2025) | 7.2 per 1,000 residents | 9.7 | 9.9 |
FBI crime data, 2025 · crimes reported to police
The July high in Winchester is 81°F. Winchester has cold, snowy winters and pleasant summers, with plenty of rain.
NOAA U.S. Climate Normals, 1991–2020
23 miles of trail in 43 parks and preserves. Town of Winchester Watershed Lands, at 1,339 acres with 1.7 miles of trail, is the biggest park or preserve. Winchester’s trail density is 0.7 miles per square mile.
| Biggest places to walk | Trails | Acres |
|---|---|---|
| 1. Laurel Ridge | 5.9 mi | 508 |
| 2. Algonquin State Forest | 2.9 mi | 646 |
| 3. Town of Winchester Watershed Lands | 1.7 mi | 1,339 |
Trails & parks © OpenStreetMap contributors · Conserved land: USGS PAD-US
The typical Winchester home is worth about $397,000, up 1.6% in a year, 11% below the Connecticut typical home.
| Winchester | Connecticut towns | U.S. towns | |
|---|---|---|---|
| Households that own their home | 66% | 81% | 73% |
| Median rent | $1,174 a month | $1,451 a month | $1,185 a month |
Zillow Home Value Index · Redfin Data Center
Museums, parks, gardens and other places to visit around Winchester. Close and well known come first.
30 mi National Historic SiteSpringfield Armory National Historic Site14K visitors a year
22 mi Theme parkLake Compounce
25 mi Stadium & arenaPeoplesBank Arena
27 mi Theme parkSix Flags New England
28 mi Stadium & arenaPratt & Whitney Stadium
35 mi LakeCandlewood LakeSpringfield Armory National Historic Site: National Park Service, Public domain · Lake Compounce: Wildcat1 at English Wikipedia, Public domain · PeoplesBank Arena: PeoplesBank Arena, CC BY 2.5 · Six Flags New England: Canadaolympic989, Public domain · Pratt & Whitney Stadium: Quintin Soloviev, CC BY 4.0 · Candlewood Lake: Carol M. Highsmith, Public domain
None within 15 miles of Winchester; the nearest are
About 4 of every 100 Winchester residents are enrolled in college, against 7 across Connecticut.
Where Winchester’s working residents go each day. Line width shows the share.
Census LEHD 2023
9 places in Winchester on the National Register of Historic Places.
3 notable people were born in Winchester.
Town in Connecticut, United States
Winchester is a town in Litchfield County, Connecticut, United States. The population was 10,224 at the 2020 census. The city of Winsted is located in Winchester. The town is part of the Northwest Hills Planning Region.
From Wikipedia, licensed CC BY-SA 4.0 · facts via Wikidata (CC0)
4 towns share a border with Winchester.
| Town | CT rank | Overall | Cost | Safety | Schools | Health |
|---|---|---|---|---|---|---|
| Winchester | #93 | B− | C+ | B+ | C+ | B+ |
| Torrington | #134 | C− | C− | B | C− | B |
| Colebrook | — | — | C | — | B+ | A |
| Barkhamsted | #50 | A− | B− | — | B | A+ |
| Winsted | — | — | — | — | — | — |
Colebrook has fewer than 2,500 residents, so it gets subject grades but no overall grade. Colebrook and Barkhamsted report no FBI crime data of their own. Winsted isn’t graded (fewer than 1,000 residents, or not enough data). Compare Winchester with a neighbor →
Short answers, built from the data on this page.
Winchester grades B− overall, better than 54% of U.S. towns and #93 of 151 in Connecticut. It grades B+ for health, B+ for safety and C+ for schools. Hazard risk is its weak spot, with a D.
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 Mary A. Swift and Phineas Miner.
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