Each edition grades its towns against each other only.
Chester's standout: crime is low: it reports less per resident than 98% of U.S. towns. Overall it grades B+, ranked 18th of 71 in Vermont. It is healthier than 89% of U.S. towns and it is easier to get around on foot or by transit than 75% of U.S. towns. Its weakest subject is schools: its schools rank behind 77% of the state's. History is its standout character grade: an A+, better than 99% of U.S. towns, with 6 places on the National Register. Only 7 of Vermont’s 172 towns score lower on hazard risk. Its National Register listings include Stone Village Historic District and Jeffrey House. 14% of residents are under 18 in Chester, below both Vermont’s towns (19%) and U.S. towns (22%).
Where Chester beats most towns.
Census counts: 981 in 1790, 3,005 in 2020. The archive holds 24 old photos and papers going back to 1850 and 3 maps from 1929 on.
6 places on the National Register of Historic Places.
Each subject compared with towns across the country (schools within Vermont), ordered by how far Chester is from typical.
How TownRatings grades towns →
Who provides power, water and the rest in Chester, and how to reach them.
EPA SDWIS (Oct 9, 2026) · HIFLD + EIA-861 2025 · Census 2020 ZCTAs · NCES 2024–25 · registration: vote.gov, updated Aug 3, 2026.
Ordered by what stands out in Chester.
Chester is a second-home town and gets more snow than nearly all U.S. towns, but it carries more natural-hazard risk than most of Vermont (mostly inland flooding).
Violent crime is rare: 1 reported in 2025, 0.3 per 1,000 residents.
Chester’s property crime rate is 1.3 per 1,000 residents.
| Chester | Vermont towns | U.S. towns | |
|---|---|---|---|
| Property crimes per 1,000 (2025) | 1.3 per 1,000 residents | 14.2 | 9.9 |
| Violent crimes per 1,000 (2025) | 0.3 per 1,000 residents | 1.8 | 1.6 |
FBI crime data, 2025 · crimes reported to police
Its public schools are run by the Green Mountain Unified School District #77. Its two schools are below. The largest public high school is Green Mountain Union High School, with 300 students.
| School | Level | Students | Letter |
|---|---|---|---|
| Chester Andover Elementary SchoolLargest public elementary schoolGrades PK–6 | Grades PK–6 | 246 | C− |
| Green Mountain Union High SchoolLargest public high schoolGrades 7–12 | Grades 7–12 | 300 | B− |
NCES · EDFacts · graded within VT on state tests and graduation
15% of adults report frequent mental distress in Chester. Chester beats the Vermont average on 7 of 31 CDC measures and trails it on 1. 28% of adults have obesity in Chester.
| Chester | Vermont towns | U.S. towns | |
|---|---|---|---|
| Frequent mental distress (CDC PLACES) | 15% | 16% | 17% |
| Obesity (CDC PLACES) | 28% | 30% | 35% |
| Sleep under 7 hours (CDC PLACES) | 30% | 30% | 36% |
| Food insecurity (CDC PLACES) | 7.4% | 9.5% | 14% |
| What stands out | Chester | VT |
|---|---|---|
| Fewer adults facing food insecurity | 7.4% | 9.2% |
| Fewer adults without reliable transportation | 5.3% | 6.4% |
| More adults who have had cancer | 11.2% | 9.9% |
CDC PLACES 2025 · modeled estimates for adults · CMS · HRSA
44 miles of trail in 0 parks and preserves. Only 6 of the 71 Vermont towns we compare have a lower share of conserved land than Chester. The trail density in Chester is 0.8 miles per square mile.
| Chester | Vermont towns | U.S. towns | |
|---|---|---|---|
| Conserved land | 4.2% | 14% | 4.3% |
| Miles of trail per square mile | 0.8 miles per square mile | 0.6 | 0.4 |
Trails & parks © OpenStreetMap contributors · Conserved land: USGS PAD-US
Jobs based in Chester fell to 652 in 2023, 65 fewer than in 2013. 7% of Chester residents live below the poverty line. The top destinations are Springfield (17%), Ludlow (10%) and Rockingham (3%).
| Chester | Vermont towns | U.S. towns | |
|---|---|---|---|
| Average trip to work | 28 minutes | 22 minutes | 25 minutes |
| Median household income | $62,000 | $81,000 | $80,000 |
| Below the poverty line | 7% | 9.6% | 9.6% |
Census LEHD 2023 · ACS
FEMA rates its natural-hazard risk higher than 96% of Vermont towns, with expected losses of about $609 per resident a year; that rating is what its C− for hazard risk is built on.
Among 71 Vermont towns, just 3 have a higher FEMA risk score than Chester. Since 1984, 45 flood insurance claims have been paid out in Chester.
FEMA flood insurance claims · FEMA National Risk Index · OpenFEMA
The Ludlow weather station, 9 miles away, records that 91 inches of snow fall in a normal winter, more than in 96% of U.S. towns.
Chester has cold, snowy winters and pleasant summers, with plenty of rain. July afternoons reach 80° and January nights drop to 10°.
NOAA U.S. Climate Normals, 1991–2020
The typical Chester home is worth about $339,000, down 1.4% in a year, 13% below the Vermont typical home.
| Chester | Vermont towns | U.S. towns | |
|---|---|---|---|
| Households that own their home | 87% | 75% | 73% |
| Median rent | $960 a month | $1,137 a month | $1,185 a month |
Zillow Home Value Index · Redfin Data Center
Museums, parks, gardens and other places to visit around Chester. Close and well known come first.
39 mi MountainMount Monadnock
24 mi Ski areaKillington Resort184 runs · 3,031 ft vertical
10 mi Ski areaOkemo Mountain119 runs · 2,165 ft vertical
19 mi Ski areaStratton Mountain Resort106 runs · 1,899 ft vertical
26 mi Ski areaMount Snow119 runs · 1,648 ft vertical
16 mi Ski areaBromley Mountain Ski Resort;Bromley Mountain67 runs · 1,297 ft verticalMount Monadnock: Jonwmcinenrey, CC BY-SA 4.0 · Killington Resort: NHRHS2010, CC BY-SA 3.0 · Okemo Mountain: Jrclark (talk), CC BY-SA 3.0 · Stratton Mountain Resort: Rudi Riet from Washington, DC, United States, CC BY-SA 2.0 · Mount Snow: William J Sisti from Morristown, NJ, USA, CC BY-SA 2.0 · Bromley Mountain Ski Resort;Bromley Mountain: Jrclark (talk), CC BY-SA 3.0
None within 15 miles of Chester; the nearest are
About 5 of every 100 Chester residents are enrolled in college, against 7 across Vermont.
Where Chester’s working residents go each day. Line width shows the share.
Census LEHD 2023
6 places in Chester on the National Register of Historic Places.
9 notable people were born in Chester.
Town in Vermont, United States
Chester is a town in Windsor County, Vermont, United States. The population was 3,005 at the 2020 census.
From Wikipedia, licensed CC BY-SA 4.0 · facts via Wikidata (CC0)
5 towns share a border with Chester.
| Town | VT rank | Overall | Cost | Safety | Schools | Health |
|---|---|---|---|---|---|---|
| Chester | #18 | B+ | B− | A+ | C− | A |
| Springfield | #56 | C− | B | B− | D | B |
| Andover | — | — | — | — | — | — |
| Ludlow | — | — | C− | — | C− | A |
| Windham | — | — | — | — | — | — |
| Grafton | — | — | — | — | — | — |
Ludlow has fewer than 2,500 residents, so it gets subject grades but no overall grade. Ludlow reports no FBI crime data of its own. Andover, Windham and Grafton aren’t graded (fewer than 1,000 residents, or not enough data). Compare Chester with a neighbor →
Short answers, built from the data on this page.
By most measures, yes. Chester grades B+ overall, better than 73% of U.S. towns and #18 of 71 in Vermont. It grades A for health, A+ for safety and C− for schools. Schools is its weak spot, with a C−.
That is 4.1 years of the area's median household income ($83,269 across the Lebanon-Claremont, NH-VT area). Cost of living, which also weighs rents, property taxes and how many households pay 30% or more of their income for housing, grades B−.
9 notable people were born here, including Donald J. Cram and Franklin Edson.
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