Each edition grades its towns against each other only.
Winchester's standout: natural-hazard risk is low. Overall it grades C−, ranked 223rd of 249 in Virginia. It is more walkable than 90% of U.S. towns and it has 9 miles of trail. Its weakest subject is safety: its crime rate is higher than 77% of U.S. towns, with 62 violent crimes reported to the FBI in 2025. History is its standout character grade: an A+, better than 97% of U.S. towns, with 35 places on the National Register. 29% of working residents work locally in Winchester, against 4.8% in Virginia’s towns and 8% across U.S. towns. Its National Register listings include Patsy Cline House and Winchester National Cemetery. Among 253 Virginia towns, just 6 have a lower January low than Winchester.
Where Winchester beats most towns.
Patsy Cline House
Patsy Cline House is one of 2 National Historic Landmarks here, the National Register’s top tier.
The archive holds 18 old photos and papers going back to 1844 and 5 maps from 1942 on.
30 places on the National Register of Historic Places.
Each subject compared with towns across the country (schools within Virginia), 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 draws workers from Front Royal and beyond and has seen reported crime fall beyond ordinary swings, but it has poverty well above the Virginia rate.
25,567 jobs are based in Winchester, 2.1 for every working resident, so most of the people who work here commute in. The average commute takes 19.6 minutes, against 27.3 across Virginia.
About one in 3 of Winchester’s working residents works in town. 22% of Winchester residents live below the poverty line. The top destinations are Front Royal (1%), Leesburg (1%) and Harrisonburg (1%).
| Winchester | Virginia towns | U.S. towns | |
|---|---|---|---|
| Below the poverty line | 22% | 7.7% | 9.6% |
| Average trip to work | 20 minutes | 27 minutes | 25 minutes |
| Median household income | $64,000 | $102,000 | $80,000 |
| Work from home | 14% | 18% | 11% |
Census LEHD 2023 · ACS
Its public schools are run by the Winchester City Public Schools. Two of its 10 schools are below, each with why it’s listed.
| School | Level | Students | Letter |
|---|---|---|---|
| James Wood MiddleLargest public middle schoolGrades 6–8 | Grades 6–8 | 873 | C− |
| John Handley HighLargest public high schoolGrades 9–12 | Grades 9–12 | 1,361 | B |
NCES · EDFacts · graded within VA on state tests and graduation
Expected storm and flood damage is lower than in 94% of U.S. communities. Since 1978, 9 flood insurance claims have been paid out in Winchester.
FEMA flood insurance claims · FEMA National Risk Index · OpenFEMA
8.9 miles of trail in 11 parks and preserves. Winchester’s trail density is 1.0 miles per square mile. The biggest place to walk is Jim Barnett Park, 166 acres with 1.2 miles of trail.
| Winchester | Virginia towns | U.S. towns | |
|---|---|---|---|
| Conserved land | 9.9% | 4.6% | 4.3% |
| Miles of trail per square mile | 1.0 miles per square mile | 0.7 | 0.4 |
| Biggest places to walk | Trails | Acres |
|---|---|---|
| 1. Kernstown Battlefield Park | 1.7 mi | 54 |
| 2. Jim Barnett Park | 1.2 mi | 166 |
| 3. Frederick Douglass Park | 0.3 mi | 5 |
Trails & parks © OpenStreetMap contributors · Conserved land: USGS PAD-US
Reported crimes fell from 782 to 664 over the last three FBI years, a drop beyond ordinary year-to-year swings.
The property crime rate in Winchester is 21.6 per 1,000 residents. Winchester reports more crime per resident than most U.S. towns we grade: about 77% report less.
| Winchester | Virginia towns | U.S. towns | |
|---|---|---|---|
| Property crimes per 1,000 (2025) | 21.6 per 1,000 residents | 14.5 | 9.9 |
| Violent crimes per 1,000 (2025) | 2.2 per 1,000 residents | 2.3 | 1.6 |
FBI crime data, 2025 · crimes reported to police
Winchester beats the Virginia average on 0 of 32 CDC measures and trails it on 15. 19% of adults report frequent mental distress in Winchester.
| Winchester | Virginia towns | U.S. towns | |
|---|---|---|---|
| Frequent mental distress (CDC PLACES) | 19% | 16% | 17% |
| Fair or poor health (CDC PLACES) | 23% | 17% | 19% |
| Frequent physical distress (CDC PLACES) | 15% | 12% | 14% |
| No health insurance, 18–64 (CDC PLACES) | 13% | 8.4% | 8.1% |
| What stands out | Winchester | VA |
|---|---|---|
| More uninsured adults | 13.1% | 8.7% |
| More adults facing food insecurity | 18.9% | 13.1% |
| More adults without reliable transportation | 10.4% | 7.4% |
CDC PLACES 2025 · modeled estimates for adults · CMS · HRSA
Winchester has chilly winters and warm summers. July afternoons reach 86°, January nights drop to 23° and about 23 inches of snow falls in a winter.
NOAA U.S. Climate Normals, 1991–2020
The typical Winchester home is worth about $399,000, up 1% in a year, close to the Virginia typical home.
| Winchester | Virginia towns | U.S. towns | |
|---|---|---|---|
| Households that own their home | 44% | 68% | 73% |
| Renters paying 30%+ of income on rent | 55% | 47% | 48% |
| Median rent | $1,315 a month | $1,764 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.
Big draw17 mi LandmarkMount Weather Emergency Operations Center
18 mi National ParkShenandoah National Park1.7M visitors a year
30 mi National BattlefieldAntietam National Battlefield161K visitors a year
39 mi CaveLuray Caverns
22 mi National Historical ParkHarpers Ferry National Historical Park538K visitors a year
in town MuseumMuseum of the Shenandoah ValleyMount Weather Emergency Operations Center: Unknown, Public domain · Shenandoah National Park: Image copyright 2005 by user G. Edward Johnson (user Lorax) and released under t, CC BY-SA 3.0 · Antietam National Battlefield: Acroterion, CC BY-SA 4.0 · Luray Caverns: Paulo Ordoveza from Washington, DC, CC BY 2.0 · Harpers Ferry National Historical Park: Mark Fickett, CC BY 3.0 · Museum of the Shenandoah Valley: GustaveCourbet, Public domain
2 within 15 miles of the center of Winchester
About 9 of every 100 Winchester residents are enrolled in college, against 7 across Virginia.
30 places in Winchester on the National Register of Historic Places.
37 notable people were born in Winchester.
Independent city in Virginia, United States
Winchester is the northernmost independent city in the Commonwealth of Virginia, United States. It is the county seat of Frederick County, although the two are separate jurisdictions. As of 2020 United States census, the city's population was 28,120. It is the principal city of the Winchester metropolitan area with a population of just over 145,000 extending into West Virginia, which is a part of the Washington–Baltimore combined statistical area. Winchester is home to Shenandoah University and the Museum of the Shenandoah Valley.
From Wikipedia, licensed CC BY-SA 4.0 · facts via Wikidata (CC0)
Short answers, built from the data on this page.
Winchester grades C− overall, better than 16% of U.S. towns and #223 of 249 in Virginia. It grades C for health, C− for safety and B− for schools. Safety is its weak spot, with a C−.
That is 4.7 years of the area's median household income ($84,298 across the Winchester, VA-WV 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.
37 notable people were born here, including Richard E. Byrd and Patsy Cline.
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