Each edition grades its towns against each other only.
Middlebury is one of the best-graded places in America: an A, 10th among Connecticut's 151 graded towns. CDC estimates put its residents' health ahead of 93% of the country, the median household earns $133K, and crime is low: it reports less per resident than 86% of U.S. towns. Its lowest mark, a C, is in cost of living. 19% of the land in Middlebury is conserved, above both the Connecticut town median (14%) and the median of U.S. towns (4.3%). Middlebury has 4 places on the National Register of Historic Places, among them Tranquility Farm and Middlebury Center Historic District. Middlebury is more walkable than 77% of U.S. towns.
Where Middlebury beats most towns.
Census counts: 838 in 1820, a low of 566 in 1890, 7,574 in 2020. The archive holds 12 old photos and papers going back to 1800 and 6 maps from 1893 on.
4 places on the National Register of Historic Places.
Each subject compared with towns across the country (schools within Connecticut), ordered by how far Middlebury is from typical.
How TownRatings grades towns →
Museums, parks, gardens and other places to visit around Middlebury. Close and well known come first.
17 mi Stadium & arenaYale Bowl
13 mi Theme parkLake Compounce
18 mi LakeCandlewood Lake
29 mi Stadium & arenaPeoplesBank Arena
5 mi Theme parkHoly Land USA
31 mi Stadium & arenaPratt & Whitney StadiumYale Bowl: Kenneth Zirkel, CC BY-SA 4.0 · Lake Compounce: Wildcat1 at English Wikipedia, Public domain · Candlewood Lake: Carol M. Highsmith, Public domain · PeoplesBank Arena: PeoplesBank Arena, CC BY 2.5 · Holy Land USA: Unknown authorUnknown author, Public domain · Pratt & Whitney Stadium: Quintin Soloviev, CC BY 4.0
Who provides power, water and the rest in Middlebury, 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 Middlebury.
Middlebury reports less crime than Naugatuck or any other graded neighbor and trades workers with Waterbury and other neighbors, but it has homes that cost more against local pay than most of Connecticut.
Its widest gap with Connecticut is food insecurity: 7.2% of its 5,926 adults worry about having enough food, against 14.9% statewide.
8.5% of Middlebury adults smoke cigarettes, against 9.7% in Connecticut’s towns and 14% across U.S. towns. 12% of Middlebury adults say their health is fair or poor. Middlebury beats the Connecticut average on 13 of 32 CDC measures and trails it on 2.
| Middlebury | Connecticut towns | U.S. towns | |
|---|---|---|---|
| Smoke cigarettes (CDC PLACES) | 8.5% | 9.7% | 14% |
| Fair or poor health (CDC PLACES) | 12% | 14% | 19% |
| Yearly checkup (CDC PLACES) | 82% | 81% | 79% |
| Frequent physical distress (CDC PLACES) | 11% | 12% | 14% |
| What stands out | Middlebury | CT |
|---|---|---|
| Fewer adults facing food insecurity | 7.2% | 14.9% |
| Fewer uninsured adults | 5% | 10% |
| More adults who have had cancer | 10.7% | 8.5% |
CDC PLACES 2025 · modeled estimates for adults · CMS · HRSA
Its public schools are run by the Regional School District 15.
| School | Level | Students | Letter |
|---|---|---|---|
| Long Meadow Elementary SchoolLargest public elementary schoolGrades PK–5 | Grades PK–5 | 518 | A− |
| Westover School PrivateLargest high schoolGrades 9–12 | Grades 9–12 | 142 | – |
| Middlebury Elementary SchoolTop results in townGrades PK–5 | Grades PK–5 | 309 | A− |
NCES · EDFacts · graded within CT on state tests and graduation
Its A tops all 3 graded towns on its borders; Naugatuck (B) comes closest. Violent crime is rare: 2 reported in 2025, 0.2 per 1,000 residents.
The property crime rate in Middlebury is 5.4 per 1,000 residents.
| Middlebury | Connecticut towns | U.S. towns | |
|---|---|---|---|
| Property crimes per 1,000 (2025) | 5.4 per 1,000 residents | 9.7 | 9.9 |
| Violent crimes per 1,000 (2025) | 0.2 per 1,000 residents | 0.4 | 1.6 |
FBI crime data, 2025 · crimes reported to police
23 miles of trail in 50 parks and preserves. Middlebury’s trail density is 1.3 miles per square mile. Hop Brook Lake Recreation Area, at 243 acres with 3 miles of trail, is the biggest park or preserve.
| Biggest places to walk | Trails | Acres |
|---|---|---|
| 1. Hop Brook Lake Recreation Area | 3 mi | 243 |
| 2. Larkin State Park Trail | 1.8 mi | 29 |
| 3. Juniper Hill | 1.4 mi | 134 |
Trails & parks © OpenStreetMap contributors · Conserved land: USGS PAD-US
At 6.4 years of the Waterbury metro’s $86K median household income, the typical home (about $548K) costs more against local pay than in 83% of Connecticut towns; that ratio is one input to its C for cost of living.
The typical Middlebury home is worth about $548,000, up 1.6% in a year, 23% above the Connecticut typical home. 88% of households own their home in Middlebury.
Census ACS, 2020–24 · Zillow Home Value Index · Redfin Data Center
Middlebury has chilly, snowy winters and pleasant summers, with plenty of rain. July afternoons reach 83°, January nights drop to 17° and about 47 inches of snow falls in a winter.
NOAA U.S. Climate Normals, 1991–2020
Middlebury has about as many jobs (3,866) as working residents, but only 364 people both live and work here.
Most working residents leave Middlebury for work: only 10% work in town. Jobs based in Middlebury grew to 3,866 in 2023, 261 more than in 2013. The top destinations are Waterbury (12%), Southbury (5%) and Danbury (4%).
| Middlebury | Connecticut towns | U.S. towns | |
|---|---|---|---|
| Median household income | $133,000 | $109,000 | $80,000 |
| Work from home | 15% | 16% | 11% |
| Below the poverty line | 5.8% | 5.8% | 9.6% |
Census LEHD 2023 · ACS
Expected storm and flood damage is lower than in 56% of U.S. communities. Since 1979, 12 flood insurance claims have been paid out in Middlebury.
FEMA flood insurance claims · FEMA National Risk Index · OpenFEMA
3 within 15 miles of the center of Middlebury
About 6 of every 100 Middlebury residents are enrolled in college, about the same as Connecticut.
4 places in Middlebury on the National Register of Historic Places.
7 notable people were born in Middlebury.
Town in Connecticut, United States
Middlebury is a town in New Haven County, Connecticut, United States. The population was 7,574 at the 2020 census. The town is part of the Naugatuck Valley Planning Region. It is a suburb of the nearby city of Waterbury to its south, and is on the northern fringe of the New York metropolitan area.
From Wikipedia, licensed CC BY-SA 4.0 · facts via Wikidata (CC0)
6 towns share a border with Middlebury.
At #10 in CT, it grades higher overall than all 6 graded towns on its borders; Watertown (B+) comes closest.
| Town | CT rank | Overall | Cost | Safety | Schools | Health |
|---|---|---|---|---|---|---|
| Middlebury | #10 | A | C | A | B+ | A |
| Southbury | #96 | B− | D | — | B+ | A |
| Naugatuck | #111 | C+ | D | B | C | A− |
| Waterbury | #150 | D− | D | C− | D | D |
| Woodbury | #102 | B− | D | — | B | A |
| Watertown | #75 | B+ | C− | B | C+ | A |
| Oxford | #82 | B | C− | — | B | A |
Southbury, Woodbury and Oxford report no FBI crime data of their own. Compare Middlebury with a neighbor →
Short answers, built from the data on this page.
Yes, by almost any measure. Middlebury grades A overall, better than 93% of U.S. towns and #10 of 151 in Connecticut. It grades A for health, A for safety and B+ for schools.
That is 6.4 years of the area's median household income ($86,191 across the Waterbury-Shelton, CT 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.
7 notable people were born here, including Grant Goodeve and Theophil Mitchell Prudden.
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