Each edition grades its towns against each other only.
Woodstock grades B− overall, ranked 99th of 151 in Connecticut, with clear strengths and some subjects that lag. Residents are healthier than 90% of U.S. towns on CDC estimates. It also does better than most on incomes: the median household earns $112K. Its lowest everyday mark is in cost of living: the typical home is worth about $444K, 4.9 years of the Putnam area’s $91K median household income. 17% of the land in Woodstock is conserved, above both Connecticut’s towns (14%) and U.S. towns (4.3%). Its National Register listings include Henry C. Bowen House and Woodstock Academy Classroom Building. Among 155 Connecticut towns, just 7 have a lower July high than Woodstock.
Where Woodstock beats most towns.
Henry C. Bowen House is a National Historic Landmark, the National Register’s top tier.
Census counts: 3,017 in 1820, a low of 1,712 in 1930, 8,221 in 2020. The archive holds 24 old photos and papers going back to 1870 and 6 maps from 1889 on.
7 places on the National Register of Historic Places.
Woodstock takes its name from Woodstock in Oxfordshire, England, 3,270 miles across the Atlantic.
UKUK editionWoodstock, settled in 1686, takes its name from Woodstock, a town in Oxfordshire, England.
1 more U.S. town is named after Woodstock:Woodstock, AL1,653
Named after: each U.S. town’s Wikipedia article. Grades compare each town with towns in its own country, so they aren’t a head-to-head.
Each subject compared with towns across the country (schools within Connecticut), ordered by how far Woodstock is from typical.
How TownRatings grades towns →
Museums, parks, gardens and other places to visit around Woodstock. Close and well known come first.
Big draw11 mi LakeLake Chaubunagungamaug
Big draw40 mi Stadium & arenaGillette Stadium
30 mi National Historic SiteSpringfield Armory National Historic Site14K visitors a year
31 mi LakeQuabbin Reservoir
31 mi Theme parkSix Flags New England
33 mi Stadium & arenaMohegan Sun ArenaLake Chaubunagungamaug: Bree from Worcester, MA, USA, CC BY-SA 2.0 · Gillette Stadium: Bernard Gagnon, CC BY-SA 3.0 · Springfield Armory National Historic Site: National Park Service, Public domain · Quabbin Reservoir: engineerchange, CC BY 2.0 · Six Flags New England: Canadaolympic989, Public domain · Mohegan Sun Arena: Bbjeter, CC BY-SA 3.0
Who provides power, water and the rest in Woodstock, 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 Woodstock.
Woodstock sends many workers across the state line to Southbridge Town and is healthy by national standards but mid-pack in Connecticut.
Within Connecticut it is healthier than 54% of the 154 graded towns: Connecticut sets a high bar. Its widest gap with Connecticut is no health insurance: 5.2% of those 18–64 have no health insurance, against 10% statewide.
29% of adults feel lonely in Woodstock, against 31% in Connecticut’s towns and 33% across U.S. towns. 13% of adults say their health is fair or poor in Woodstock. Woodstock beats the Connecticut average on 11 of 32 CDC measures and trails it on 1.
| Woodstock | Connecticut towns | U.S. towns | |
|---|---|---|---|
| Feel lonely (CDC PLACES) | 29% | 31% | 33% |
| Fair or poor health (CDC PLACES) | 13% | 14% | 19% |
| Diabetes (CDC PLACES) | 9.1% | 9.4% | 12% |
| Frequent physical distress (CDC PLACES) | 12% | 12% | 14% |
| What stands out | Woodstock | CT |
|---|---|---|
| Fewer uninsured adults | 5.2% | 10% |
| Fewer adults facing food insecurity | 7.8% | 14.9% |
| More adults who have had cancer | 10% | 8.5% |
CDC PLACES 2025 · modeled estimates for adults · CMS · HRSA
Its public schools are run by the The Woodstock Academy District. Two of its 3 schools are below, each with why it’s listed. The largest public high school is The Woodstock Academy, with 1,011 students.
| School | Level | Students | Letter |
|---|---|---|---|
| Woodstock Elementary SchoolLargest public elementary schoolGrades PK–4 | Grades PK–4 | 391 | B− |
| The Woodstock AcademyLargest public high schoolGrades 9–12 | Grades 9–12 | 1,011 | B+ |
NCES · EDFacts · graded within CT on state tests
32% of working residents cross a state line to work, Southbridge Town among the top destinations.
Most working residents leave Woodstock for work: only 13% work in town. The average trip to work in Woodstock is 31 minutes. The top destinations are Putnam (9%), Killingly (7%) and Southbridge Town (4%).
| Woodstock | Connecticut towns | U.S. towns | |
|---|---|---|---|
| Average trip to work | 31 minutes | 27 minutes | 25 minutes |
| Median household income | $112,000 | $109,000 | $80,000 |
| Below the poverty line | 4.4% | 5.8% | 9.6% |
| Working residents who work in town | 13% | 11% | 8% |
Census LEHD 2023 · ACS
30 miles of trail in 28 parks and preserves. The biggest place to walk is Nipmuck State Forest, 1,264 acres with 4.7 miles of trail. Woodstock’s trail density is 0.5 miles per square mile.
| Biggest places to walk | Trails | Acres |
|---|---|---|
| 1. Nipmuck State Forest | 4.7 mi | 1,264 |
| 2. Nightingale Forest | 1.3 mi | 144 |
| 3. Roseland Park | 0.3 mi | 102 |
Trails & parks © OpenStreetMap contributors · Conserved land: USGS PAD-US
Adults 18 to 34 are 14% of residents (22% statewide); adults 35 to 64 are 45% of residents (39% statewide). 48% of Woodstock adults 25 and older hold a bachelor’s degree or more. Woodstock has grown 2.9% since 2020, to 8,474 residents in the Census Bureau’s 2025 estimate.
| Woodstock | Connecticut towns | U.S. towns | |
|---|---|---|---|
| Median age | 49.3 years | 44.4 years | 40.5 years |
| Bachelor’s degree or more, 25+ | 48% | 45% | 29% |
| Aged 65 or older | 23% | 20% | 18% |
| Under 18 | 19% | 19% | 22% |
49% women, 51% men
That’s an even split within the survey’s margin of ±3.3 points. Across Connecticut, 50.9% of residents are women.
| Woodstock | CT | U.S. | |
|---|---|---|---|
| Under 10 | 8.8% | 10.4% | 11.6% |
| 10 to 17 | 10.2% | 9.8% | 10.3% |
| 18 to 24 | 5.5% | 9.3% | 9.1% |
| 25 to 34 | 8% | 12.6% | 13.7% |
| 35 to 44 | 13.4% | 12.7% | 13.2% |
| 45 to 54 | 9.8% | 12.5% | 12.2% |
| 55 to 64 | 21.8% | 14.2% | 12.7% |
| 65 to 74 | 13.6% | 10.7% | 10.2% |
| 75 and older | 8.9% | 7.8% | 7% |
| No diploma | 2.3% | 8.5% | 10.4% |
| High school | 20.5% | 25.3% | 26% |
| Some college | 20.4% | 16.1% | 19.1% |
| Associate’s | 9% | 7.6% | 8.8% |
| Bachelor’s | 23.5% | 23.3% | 21.6% |
| Graduate | 24.2% | 19.2% | 14.1% |
Census population estimates, 2025 · U.S. Census Bureau · ACS 2020-2024 5-year estimates
Woodstock has chilly, snowy winters and pleasant summers, with plenty of rain. July afternoons reach 81°, January nights drop to 17° and about 52 inches of snow falls in a winter.
NOAA U.S. Climate Normals, 1991–2020
Expected storm and flood damage is higher than in 56% of U.S. communities. Since 1989, 11 flood insurance claims have been paid out in Woodstock.
FEMA flood insurance claims · FEMA National Risk Index · OpenFEMA
The typical Woodstock home is worth about $444,000, up 2.9% in a year, close to the Connecticut typical home.
| Woodstock | Connecticut towns | U.S. towns | |
|---|---|---|---|
| Households that own their home | 83% | 81% | 73% |
| Median rent | $1,202 a month | $1,451 a month | $1,185 a month |
Zillow Home Value Index · Redfin Data Center
1 within 15 miles of the center of Woodstock
About 2 of every 100 Woodstock residents are enrolled in college, against 7 across Connecticut.
Where Woodstock’s working residents go each day. Line width shows the share.
Census LEHD 2023
7 places in Woodstock on the National Register of Historic Places.
17 notable people were born in Woodstock.
Town in Connecticut, United States
Woodstock is a town in Windham County, Connecticut, United States. The town is part of the Northeastern Connecticut Planning Region. The population was 8,221 at the 2020 census.
From Wikipedia, licensed CC BY-SA 4.0 · facts via Wikidata (CC0)
7 towns share a border with Woodstock.
| Town | CT rank | Overall | Cost | Safety | Schools | Health |
|---|---|---|---|---|---|---|
| Woodstock | #99 | B− | C+ | — | C+ | A |
| Pomfret | #69 | B+ | C− | — | A− | A |
| South Woodstock | — | — | — | — | — | — |
| Thompson | #123 | C | B | — | C | B+ |
| Union | — | — | — | — | — | — |
| Eastford | — | — | B− | — | B+ | A− |
| Quinebaug | — | — | — | — | — | — |
| Putnam | #126 | C | B− | B+ | C− | C+ |
Eastford has fewer than 2,500 residents, so it gets subject grades but no overall grade. Woodstock, Pomfret, Thompson and Eastford report no FBI crime data of their own. South Woodstock, Union and Quinebaug aren’t graded (fewer than 1,000 residents, or not enough data). Compare Woodstock with a neighbor →
Short answers, built from the data on this page.
Woodstock grades B− overall, better than 50% of U.S. towns and #99 of 151 in Connecticut. It grades A for health and C+ for schools. Walkability is its weak spot, with a C−.
Cost of living, which also weighs rents, property taxes and how many households pay 30% or more of their income for housing, grades C+.
17 notable people were born here, including Kenneth Lee Pike and Jared W. Williams.
