Each edition grades its towns against each other only.
For most people who can afford it, yes. Chester grades A− overall, ranked 181st of 745 in New York. It has 19 miles of trail. The median household earns $140K and residents are healthier than 86% of U.S. towns on CDC estimates. The trade-off is money: homes are expensive, about $538K for a typical one and 5.5 times the Kiryas Joel metro’s $98K median household income. Chester’s average trip to work is 42 minutes, above both New York’s towns (25 minutes) and U.S. towns (25 minutes). Chester is home to Yeshiva of Nitra Rabbinical College. Chester has 4 places on the National Register.
Where Chester beats most towns.
Census counts: 1,641 in 1850, 12,646 in 2020. The archive holds 6 old photos and papers going back to 1875 and 4 maps from 1906 on.
4 places on the National Register of Historic Places.
Each subject compared with towns across the country (schools within New York), ordered by how far Chester is from typical.
How TownRatings grades towns →
Museums, parks, gardens and other places to visit around Chester. Close and well known come first.
Big draw17 mi MuseumUnited States Military Academy
Big draw37 mi Stadium & arenaMetLife Stadium
Big draw39 mi Stadium & arenaYankee Stadium
Big draw37 mi MuseumThe Cloisters
31 mi LandmarkFerncliff Cemetery
39 mi National MemorialGeneral Grant National Memorial63K visitors a yearUnited States Military Academy: USMA Public Affairs Office, Public domain · MetLife Stadium: babyknight, CC BY 2.0 · Yankee Stadium: Matt Boulton, CC BY-SA 2.0 · The Cloisters: Paweł Drozd on Wiki Drozdpl cropped by Beyond My Ken (talk) 17:05, 27 December 2, CC BY-SA 3.0 · Ferncliff Cemetery: Anthony22 at English Wikipedia, CC BY-SA 3.0 · General Grant National Memorial: Daniel Schwen, CC BY-SA 3.0
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 trades workers with New York City and other neighbors, owes part of its health edge to its incomes and has household incomes well above the New York norm.
The biggest place to walk is Goosepond Mountain State Park, 2,050 acres with 7 miles of trail. The trail density in Chester is 0.8 miles per square mile.
| Biggest places to walk | Trails | Acres |
|---|---|---|
| 1. Goosepond Mountain State Park | 7 mi | 2,050 |
| 2. Chester Commons Park | 0.6 mi | 35 |
| 3. Knapp's View | — | 91 |
Trails & parks © OpenStreetMap contributors · Conserved land: USGS PAD-US
Its public schools are run by the Chester Union Free School District. Its two schools are below. The largest public high school is Chester Academy-Middle/High School, with 538 students.
| School | Level | Students | Letter |
|---|---|---|---|
| Chester Elementary SchoolLargest public elementary schoolGrades PK–5 | Grades PK–5 | 393 | C− |
| Chester Academy-Middle/High SchoolLargest public high schoolGrades 6–12 | Grades 6–12 | 538 | B |
NCES · EDFacts · graded within NY on state tests and graduation
Against the 3,590 U.S. towns with household incomes like Chester’s, it is less healthy than 51%: its national edge comes with its incomes.
18% of Chester adults have been diagnosed with depression. Chester beats the New York average on 14 of 32 CDC measures and trails it on 0. 30% of Chester adults have high blood pressure.
| Chester | New York towns | U.S. towns | |
|---|---|---|---|
| Depression (CDC PLACES) | 18% | 21% | 23% |
| High blood pressure (CDC PLACES) | 30% | 34% | 35% |
| Smoke cigarettes (CDC PLACES) | 11% | 13% | 14% |
| Frequent physical distress (CDC PLACES) | 12% | 14% | 14% |
| What stands out | Chester | NY |
|---|---|---|
| Fewer adults facing food insecurity | 12.3% | 17.2% |
| Fewer older adults who have lost all their teeth | 9.9% | 12.8% |
CDC PLACES 2025 · modeled estimates for adults · CMS · HRSA
Expected storm and flood damage is lower than in 77% of U.S. communities. Since 1978, 85 flood insurance claims have been paid out in Chester.
FEMA flood insurance claims · FEMA National Risk Index · OpenFEMA
Chester has chilly, snowy winters and pleasant summers. July afternoons reach 83°, January nights drop to 18° and about 39 inches of snow falls in a winter.
NOAA U.S. Climate Normals, 1991–2020
Chester has about as many jobs (4,679) as working residents, but only 391 people both live and work here. The average commute takes 42 minutes, against 32.6 across New York.
Most working residents leave Chester for work: only 7% work in town. Jobs based in Chester fell to 4,679 in 2023, 388 fewer than in 2013. 16% of workers work from home in Chester.
| Chester | New York towns | U.S. towns | |
|---|---|---|---|
| Median household income | $140,000 | $82,000 | $80,000 |
| Work from home | 16% | 12% | 11% |
| Below the poverty line | 8.1% | 9.5% | 9.6% |
| Working residents who work in town | 7.4% | 10% | 8% |
Census LEHD 2023 · ACS
Chester's reported crime rate is well below New York's. Chester’s property crime rate is 0.9 per 1,000 residents. Most reported incidents are property crimes, mainly thefts.
| Chester | New York towns | U.S. towns | |
|---|---|---|---|
| Property crimes per 1,000 (2025) | 0.9 per 1,000 residents | 7.6 | 9.9 |
| Violent crimes per 1,000 (2025) | 0.2 per 1,000 residents | 0.8 | 1.6 |
FBI crime data, 2025 · crimes reported to police
The median household earns $139,778, against $85,974 across New York, one input to its A for jobs and income.
Adults 35 to 64 are 43% of residents (39% statewide). 38% of adults 25 and older have a bachelor’s degree or more, vs 40% across New York.
| Chester | New York towns | U.S. towns | |
|---|---|---|---|
| Aged 65 or older | 15% | 20% | 18% |
| Bachelor’s degree or more, 25+ | 38% | 32% | 29% |
| Under 18 | 23% | 20% | 22% |
| Median age | 40.2 years | 43 years | 40.5 years |
54% women, 46% men
About 86 men for every 100 women (the survey’s margin: ±3.3 points). Across New York, 51.2% of residents are women.
| Chester | NY | U.S. | |
|---|---|---|---|
| Under 10 | 12.2% | 11% | 11.6% |
| 10 to 17 | 10.8% | 9.5% | 10.3% |
| 18 to 24 | 7.1% | 8.9% | 9.1% |
| 25 to 34 | 12.3% | 14.2% | 13.7% |
| 35 to 44 | 13.4% | 13% | 13.2% |
| 45 to 54 | 9.8% | 12.2% | 12.2% |
| 55 to 64 | 19.9% | 13.3% | 12.7% |
| 65 to 74 | 10.6% | 10.3% | 10.2% |
| 75 and older | 3.9% | 7.6% | 7% |
| No diploma | 1.2% | 12% | 10.4% |
| High school | 24.4% | 24.3% | 26% |
| Some college | 22.8% | 14.6% | 19.1% |
| Associate’s | 13.3% | 8.8% | 8.8% |
| Bachelor’s | 24.2% | 22.4% | 21.6% |
| Graduate | 14.1% | 17.9% | 14.1% |
U.S. Census Bureau · ACS 2020-2024 5-year estimates
The typical Chester home is worth about $538,000, up 3.2% in a year, close to the New York typical home.
| Chester | New York towns | U.S. towns | |
|---|---|---|---|
| Median rent | $1,974 a month | $1,098 a month | $1,185 a month |
| Households that own their home | 79% | 75% | 73% |
Zillow Home Value Index · Redfin Data Center
4 within 15 miles of the center of Chester
About 5 of every 100 Chester residents are enrolled in college, against 7 across New York.
4 places in Chester on the National Register of Historic Places.
Town in New York, United States
Chester is a town in Orange County, New York, United States. The population was 12,646 at the 2020 census. Chester contains a village, also called Chester. Chester is the birthplace of Philadelphia-style cream cheese.
From Wikipedia, licensed CC BY-SA 4.0 · facts via Wikidata (CC0)
6 towns share a border with Chester.
| Town | NY rank | Overall | Cost | Safety | Schools | Health |
|---|---|---|---|---|---|---|
| Chester | #181 | A− | C− | — | B+ | A |
| Blooming Grove | #319 | B | D | A− | B | B+ |
| Goshen | #133 | A | D | A | B | A |
| Warwick | #198 | A− | D | — | A− | A |
| Monroe | #496 | C+ | D− | — | B | C+ |
| Chester | #122 | A | D | B+ | B+ | A− |
| Walton Park | — | — | — | — | — | — |
Chester, Warwick and Monroe report no FBI crime data of their own. Walton Park isn’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.
For most people who can afford it, yes. Chester grades A− overall, better than 78% of U.S. towns and #181 of 745 in New York. It grades A for health and B+ for schools. Cost of living is its weak spot, with a C−.
Yes. Cost of living, which also weighs rents, property taxes and how many households pay 30% or more of their income for housing, grades C−.
