Each edition grades its towns against each other only.
For most people who can afford it, yes. Westport grades A overall, 14th of 151 graded towns in Connecticut. It is among the healthiest towns in the country on CDC estimates. Its schools rank ahead of 97% of Connecticut towns and the median household earns $250K. What holds it back is price: the typical home is worth about $2.1 million, 18.1 years of the Bridgeport metro’s $115K median household income. 80% of adults 25 and older hold a bachelor’s degree or more in Westport, where Connecticut’s towns sit at 45% and U.S. towns at 29%. Westport is more walkable than 94% of U.S. towns. Its National Register listings include Saugatuck River Bridge and Bradley-Wheeler House.
Where Westport beats most towns.
Godillot Place| Widest gap | Westport | CT |
|---|---|---|
| Fewer adults facing food insecurity | 5.6% | 14.9% |
| School | Grades | Students |
|---|---|---|
| Long Lots School | K–5 | 571 |
| Coleytown Elementary School | K–5 | 461 |
| Green's Farms School | K–5 | 460 |
Census counts: 1,803 in 1840, 27,141 in 2020. The archive holds 17 old photos and papers going back to 1855 and 4 maps from 1892 on.
18 places on the National Register of Historic Places.
Each subject compared with towns across the country (schools within Connecticut), ordered by how far Westport is from typical.
How TownRatings grades towns →
Museums, parks, gardens and other places to visit around Westport. Close and well known come first.
Big draw40 mi GardenCentral Park40.0M visitors a year
Big draw37 mi MuseumUnited States Military Academy
Big draw40 mi MuseumMetropolitan Museum of Art2.0M visitors a year
Big draw36 mi Stadium & arenaYankee Stadium
Big draw40 mi MuseumSolomon R. Guggenheim Museum1.1M visitors a year
Big draw36 mi Stadium & arenaCiti FieldCentral Park: Ed Yourdon from New York City, USA, CC BY-SA 2.0 · United States Military Academy: USMA Public Affairs Office, Public domain · Metropolitan Museum of Art: Hugo Schneider, CC BY-SA 2.0 · Yankee Stadium: Matt Boulton, CC BY-SA 2.0 · Solomon R. Guggenheim Museum: Jean-Christophe BENOIST, CC BY 3.0 · Citi Field: Chris6d, CC BY-SA 4.0
Who provides power, water and the rest in Westport, 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 Westport.
Westport is among the three healthiest towns in Connecticut, has schools in the top 5% of Connecticut and draws workers from Norwalk and beyond.
At 18.1 years of the Bridgeport metro’s $115K median household income, the typical home (about $2.07M) costs more against local pay than in 99% of Connecticut towns; that ratio is one input to its D− for cost of living.
The median rent in Westport is $2,509 a month. Typical home values rose 11% in the year to September 2026. 89% of Westport households own their home.
| Westport | Connecticut towns | U.S. towns | |
|---|---|---|---|
| Median rent | $2,509 a month | $1,448 a month | $1,185 a month |
| Households that own their home | 89% | 81% | 73% |
Census ACS, 2020–24 · Zillow Home Value Index · Redfin Data Center
Its A+ ranks #2 of the 152 Connecticut towns we grade for schools. Its A+ is the best School Grade on its borders; Weston (A) is next.
Its public schools are run by the Westport School District. Three of its 12 schools are below, each with why it’s listed.
| School | Level | Students | Letter |
|---|---|---|---|
| Bedford Middle SchoolLargest public middle schoolGrades 6–8 | Grades 6–8 | 710 | A |
| Staples High SchoolLargest public high schoolGrades 9–12 | Grades 9–12 | 1,629 | A+ |
| Green's Farms SchoolTop results in townGrades K–5 | Grades K–5 | 460 | A+ |
NCES · EDFacts · graded within CT on state tests and graduation
It ranks #3 of the 154 Connecticut towns we grade on the CDC estimates behind the Health Grade. Its widest gap with Connecticut is food insecurity: 5.6% of its 19,970 adults worry about having enough food, against 14.9% statewide.
21% of adults have obesity in Westport. Of the 154 Connecticut towns we compare, none has a lower share of adults who have been diagnosed with depression than Westport. 7.3% of adults have diabetes in Westport.
| Westport | Connecticut towns | U.S. towns | |
|---|---|---|---|
| Obesity (CDC PLACES) | 21% | 30% | 35% |
| Frequent mental distress (CDC PLACES) | 11% | 15% | 17% |
| Depression (CDC PLACES) | 17% | 22% | 23% |
| Frequent physical distress (CDC PLACES) | 9.1% | 12% | 14% |
| What stands out | Westport | CT |
|---|---|---|
| Fewer adults facing food insecurity | 5.6% | 14.9% |
| Fewer adults facing a utility shut-off | 3.5% | 8.4% |
| More adults who have had cancer | 10.3% | 8.5% |
CDC PLACES 2025 · modeled estimates for adults · CMS · HRSA
14,543 jobs are based in Westport, 1.5 for every working resident, so most of the people who work here commute in. The average commute takes 40.9 minutes, against 26.5 across Connecticut.
Among 155 Connecticut towns, just 3 have a higher median household income than Westport. Westport’s average trip to work is 41 minutes. Among 155 Connecticut towns, just 2 have a higher share of workers working from home than Westport.
| Westport | Connecticut towns | U.S. towns | |
|---|---|---|---|
| Work from home | 42% | 15% | 11% |
| Average trip to work | 41 minutes | 27 minutes | 25 minutes |
| Median household income | $250,000 | $109,000 | $80,000 |
| Below the poverty line | 3.2% | 5.8% | 9.6% |
Census LEHD 2023 · ACS
At 12.7 crimes per 1,000 residents a year, it reports less crime than 54% of Connecticut’s graded towns. Violent crime is rare: 9 reported in 2025, 0.3 per 1,000 residents.
FBI crime data, 2025 · crimes reported to police
Westport has chilly, snowy winters and warm summers, with plenty of rain. July afternoons reach 85°, January nights drop to 24° and about 34 inches of snow falls in a winter.
NOAA U.S. Climate Normals, 1991–2020
1,547 flood insurance claims have been filed here, and 230 properties have flooded more than once.
Expected storm and flood damage is higher than in 67% of U.S. communities. Since 1978, 1,547 flood insurance claims have been paid out in Westport.
FEMA flood insurance claims · FEMA National Risk Index · OpenFEMA
13 miles of trail in 31 parks and preserves. Only 8 of the 155 Connecticut towns we compare have a lower share of conserved land than Westport. The biggest place to walk is Sherwood Island State Park, 272 acres with 3 miles of trail.
| Westport | Connecticut towns | U.S. towns | |
|---|---|---|---|
| Miles of trail per square mile | 0.4 miles per square mile | 1.3 | 0.4 |
| Conserved land | 4.3% | 14% | 4.3% |
| Biggest places to walk | Trails | Acres |
|---|---|---|
| 1. Sherwood Island State Park | 3 mi | 272 |
| 2. H. Smith Richardson Wildlife Preserve | 1.9 mi | 55 |
| 3. Winslow Park | 1.1 mi | 29 |
Trails & parks © OpenStreetMap contributors · Conserved land: USGS PAD-US
5 within 15 miles of the center of Westport
About 3 of every 100 Westport residents are enrolled in college, against 7 across Connecticut.
Coastal flooding makes up 8% of the storm damage FEMA expects here.
FEMA National Risk Index · OpenFEMA · OpenStreetMap
18 places in Westport on the National Register of Historic Places.
Town in Connecticut, U.S.
Westport is a town in Fairfield County, Connecticut, United States. Located in the Gold Coast along the Long Island Sound, it is 48 miles (77 km) northeast of New York City and is part of the Western Connecticut Planning Region.
From Wikipedia, licensed CC BY-SA 4.0 · facts via Wikidata (CC0)
10 towns share a border with Westport.
| Town | CT rank | Overall | Cost | Safety | Schools | Health |
|---|---|---|---|---|---|---|
| Westport | #14 | A | D− | B+ | A+ | A+ |
| Fairfield | #38 | A− | D | B | A− | A+ |
| Norwalk | #109 | C+ | D− | B | C | A |
| Staples | — | — | — | — | — | — |
| Greens Farms | — | — | — | — | — | — |
| Southport | — | — | — | — | — | — |
| Weston | #8 | A+ | D− | A+ | A | A+ |
| Saugatuck | — | — | — | — | — | — |
Staples, Greens Farms, Southport and Saugatuck aren’t graded (fewer than 1,000 residents, or not enough data). Compare Westport with a neighbor →
Short answers, built from the data on this page.
For most people who can afford it, yes. Westport grades A overall, better than 91% of U.S. towns and #14 of 151 in Connecticut. It grades A+ for health, B+ for safety and A+ 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−.
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