Each edition grades its towns against each other only.
39,964 people live in this town, settled in 1901.
The everyday basics are strong; the price of a home is the catch. On health it is strong: CDC estimates put its residents' health ahead of 96% of the country. At B+ overall, Ossining is better than just over two thirds of U.S. towns and ranks 258th of 745 in New York. It also does well on walkability: it is more walkable than 98% of U.S. towns. What counts against it is cost of living: the typical home is worth about $553K, 5.6 years of the New York metro’s $99K median household income. This New York town has 13 places on the National Register of Historic Places, among them Highland Cottage and St. Paul's Episcopal Church and Rectory. Its midpoint rent is $2,203 a month, above both the New York town median ($1,098 a month) and the median of U.S. towns ($1,185 a month). The town’s density of trails is 1.2 miles per square mile, where New York’s towns sit at 0.4 and U.S. towns at 0.4.
Figures: health, CDC PLACES · home values, Zillow · incomes, Census ACS, 2020–24 · National Register of Historic Places · OpenStreetMap.
Where Ossining beats most towns.
Census counts: 4,939 in 1850, 40,061 in 2020. The archive holds 12 old photos and papers going back to 1809 and 7 maps from 1892 on.
13 places on the National Register of Historic Places.
Each subject compared with towns across the country (schools within New York), ordered by how far Ossining is from typical.
Its grades run from A+ for walkability (better than 98% of comparable towns) to D− for cost of living (better than 2%), so the B+ overall blends very different results.
How TownRatings grades towns →
Museums, parks, gardens and other places to visit around Ossining. Close and well known come first.
Big draw17 mi MuseumUnited States Military Academy
Big draw27 mi City parkCentral Park40.0M visitors a year
Big draw29 mi Stadium & arenaMadison Square Garden
Big draw26 mi Stadium & arenaMetLife Stadium
Big draw28 mi TheatreStudio 54
Big draw27 mi MuseumMetropolitan Museum of Art2.0M visitors a yearUnited States Military Academy: USMA Public Affairs Office, Public domain · Central Park: Ed Yourdon from New York City, USA, CC BY-SA 2.0 · Madison Square Garden: Ajay Suresh from New York, NY, USA, CC BY 2.0 · MetLife Stadium: babyknight, CC BY 2.0 · Studio 54: Americasroof (talk), CC BY-SA 3.0 · Metropolitan Museum of Art: Hugo Schneider, CC BY-SA 2.0
Who provides power, water and the rest in Ossining, 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 Ossining.
Pocantico Park, at 64 acres with 1.5 miles of trail, is the biggest park or preserve. Trails total 18 miles in 15 parks and preserves.
| Ossining | New York towns | U.S. towns | |
|---|---|---|---|
| Miles of trail per square mile | 1.2 miles per square mile | 0.4 | 0.4 |
| Conserved land | 6.5% | 5.2% | 4.3% |
| Biggest places to walk | Trails | Acres |
|---|---|---|
| 1. Old Croton Aqueduct State Park | 3.4 mi | 44 |
| 2. Pocantico Park | 1.5 mi | 64 |
| 3. Crawbuckie Nature Preserve | 1.1 mi | 35 |
Trails & parks © OpenStreetMap contributors · Conserved land: USGS PAD-US
Two of its 8 schools are below, each with the reason it’s listed. The Ossining Union Free School District runs its public schools. Public school enrollment in the town: 3,382 students across 5 schools.
| School | Level | Students | Letter |
|---|---|---|---|
| Anne M Dorner Middle SchoolLargest public middle schoolGrades 6–8 | Grades 6–8 | 1,032 | B− |
| Ossining High SchoolLargest public high schoolGrades 9–12 | Grades 9–12 | 1,577 | A |
NCES · EDFacts · graded within NY on state tests and graduation
Its widest gap with New York is tooth loss: 6% of those 65+ have lost all their teeth, against 12.8% statewide.
The share of adults in Ossining who feel lonely: 29%. The town does better than the New York average on 24 of 32 CDC measures and worse on 1. In Ossining, 12% of adults report frequent mental distress, and 24% have obesity.
| Ossining | New York towns | U.S. towns | |
|---|---|---|---|
| Depression (CDC PLACES) | 15% | 21% | 23% |
| Frequent mental distress (CDC PLACES) | 12% | 16% | 17% |
| Obesity (CDC PLACES) | 24% | 33% | 35% |
| Smoke cigarettes (CDC PLACES) | 8.1% | 13% | 14% |
| What stands out | Ossining | NY |
|---|---|---|
| Fewer older adults who have lost all their teeth | 6% | 12.8% |
| Fewer adults facing food insecurity | 10.2% | 17.2% |
| More adults who have had cancer | 9.3% | 7.7% |
CDC PLACES 2025 · modeled estimates for adults · CMS · HRSA
15 flood insurance claims have been paid in Ossining since 1978. Compared with 92% of U.S. communities, expected storm and flood damage here is lower. Expected losses in Ossining break down as 62% from inland flooding and 9% from hurricanes.
FEMA flood insurance claims · FEMA National Risk Index · OpenFEMA
The top destinations are New York (30%), Mount Pleasant (6%) and Greenburgh (6%). For most workers, Ossining is a place to come home to: only 11% work in town. The town’s average commute comes in at 37 minutes. Half of commuters travel less than 17 miles.
| Ossining | New York towns | U.S. towns | |
|---|---|---|---|
| Average trip to work | 37 minutes | 25 minutes | 25 minutes |
| Median household income | $126,000 | $82,000 | $80,000 |
| Work from home | 18% | 12% | 11% |
| Working residents who work in town | 11% | 10% | 8% |
Census LEHD 2023 · ACS
NOAA U.S. Climate Normals, 1991–2020
48% of adults 25 and older hold a bachelor’s degree or more in Ossining. Adults 18 to 34 are 18% of residents (23% statewide); adults 35 to 64 are 43% of residents (39% statewide). In Ossining, the median age is 43.5 years.
| Ossining | New York towns | U.S. towns | |
|---|---|---|---|
| Bachelor’s degree or more, 25+ | 48% | 32% | 29% |
| Median age | 43.5 years | 42.9 years | 40.5 years |
| Under 18 | 20% | 20% | 22% |
49% women, 51% men
That’s an even split within the survey’s margin of ±1.4 points. Across New York, 51.2% of residents are women. Median age: women 45.3, men 42.3.
| Ossining | NY | U.S. | |
|---|---|---|---|
| Under 10 | 10.7% | 11% | 11.6% |
| 10 to 17 | 8.8% | 9.5% | 10.3% |
| 18 to 24 | 7.3% | 8.9% | 9.1% |
| 25 to 34 | 10.7% | 14.2% | 13.7% |
| 35 to 44 | 14.3% | 13% | 13.2% |
| 45 to 54 | 15.5% | 12.2% | 12.2% |
| 55 to 64 | 13.1% | 13.3% | 12.7% |
| 65 to 74 | 11% | 10.3% | 10.2% |
| 75 and older | 8.6% | 7.6% | 7% |
| No diploma | 15.3% | 12% | 10.4% |
| High school | 16.5% | 24.3% | 26% |
| Some college | 14.2% | 14.6% | 19.1% |
| Associate’s | 6% | 8.8% | 8.8% |
| Bachelor’s | 20.3% | 22.4% | 21.6% |
| Graduate | 27.7% | 17.9% | 14.1% |
U.S. Census Bureau · ACS 2020-2024 5-year estimates
26 within 15 miles of the center of Ossining
About 5 of every 100 Ossining residents are enrolled in college, against 7 across New York.
Where Ossining’s working residents go each day. Line width shows the share.
Census LEHD 2023
13 places in Ossining on the National Register of Historic Places.
20 notable people were born in Ossining.
Town in New York, United States
Ossining ( OSS-in-ing) is a town located along the Hudson River in Westchester County, New York. The population was 40,061 at the time of the 2020 census. It contains two villages, the Village of Ossining and part of Briarcliff Manor, the rest of which is located in the Town of Mount Pleasant. Ossining is the location of Sing Sing maximum-security prison.
From Wikipedia, licensed CC BY-SA 4.0 · facts via Wikidata (CC0)
8 towns share a border with Ossining.
All 6 graded towns on its borders grade higher than its B+; Clarkstown (A−) is closest.
| Town | NY rank | Overall | Cost | Safety | Schools | Health |
|---|---|---|---|---|---|---|
| Ossining | #258 | B+ | D− | — | B− | A+ |
| Mount Pleasant | #90 | A | D− | — | A | A+ |
| Croton-on-Hudson | #24 | A+ | D | A | A | A+ |
| Cortlandt | #155 | A− | D | — | A− | A |
| Briarcliff Manor | #179 | A− | D− | — | B− | A+ |
| Ossining | #433 | B− | D− | — | C− | A |
| Clarkstown | #201 | A− | D− | B− | A− | A |
| New Castle | #42 | A+ | D− | — | A+ | A+ |
Ossining, Mount Pleasant, Cortlandt, Briarcliff Manor, Ossining and New Castle report no FBI crime data of their own. Compare Ossining with a neighbor →
Short answers, built from the data on this page.
For most people who can afford it, yes. Ossining grades B+ overall, better than 68% of U.S. towns and #258 of 745 in New York. It grades A+ for health and B− for schools. Cost of living is its weak spot, with a D−.
Yes. Cost of living, which also weighs rents, property taxes and how many households pay 30% or more of their income for housing, grades D−.
20 notable people were born here, including Kara DioGuardi and Jesse Lee Soffer.
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