Each edition grades its towns against each other only.
Among the most historic 1% of U.S. towns · #18 of 283 in Massachusetts. What drives it
67 places in town are on the National Register, among them four historic districts with 422 buildings between them. Below: maps from 1893 on and the census since 1850.
Winchester dates its founding to 1640 (Wikidata). The census first counted it in 1850.
Among the most historic 1% of U.S. towns, on its age, its old homes and the National Register.
On its age, its old homes and the National Register, Winchester is among the most historic 1% of U.S. towns, #18 of 283 in Massachusetts. All 3 inputs put Winchester near the top nationally; its age ranks highest.
Massachusetts towns list more on the Register than most of the country (a typical Massachusetts town has 46.0 per 10,000 residents, the U.S. 2.4), so Winchester’s 217 sits above most of its state (77% of Massachusetts towns have fewer) while its 507 historic buildings outnumber those of 97% of U.S. towns.
Founding year: Wikidata (other dates in Quick answers). Homes: Census ACS 2020–24. National Register: National Park Service, May 2026 list; each listing counted once (boundary changes and added documentation belong to their listing), and a historic district counts its contributing buildings. How TownRatings grades history →
Read from the archive, the National Register and the record. The page puts what stands out first.
The country’s official list of buildings and places worth saving.
National Park Service, National Register of Historic Places. Photos from Wikimedia Commons, credited on each place’s page.
Woven from the archive, old maps, post office records, the National Register and the people born here.
BuiltHouse at 114 Marble Street is builtBuiltWinchester Town Hall is builtBuiltWinchester Savings Bank is built
On the mapFirst mapped by the U.S. Geological SurveyBuiltSanborn House is built
Born hereMaribel Vinson is born here
Born hereBrad Whitford is born here
Born hereRichard Phillips is born here
Born hereMark A. Milley is born hereFrom Wikipedia’s history of Winchester.
Native Americans inhabited the area that would become Winchester for thousands of years prior to European colonization of the Americas. At the time of contact, the area was inhabited by the Naumkeag people, from whom the land that would become Winchester was purchased for the settlement of Charlestown in 1639.
Text from Wikipedia, licensed CC BY-SA 4.0.
Passages that mention Winchester, cut from the printed page as they were published.
3 Or to the comer of <.'ross Street, or its equivalent, the main highway being Main Street from Woburn Common to that point. Cross Street wm the way to the Richardsons (on Richardson's Row, or Washington Street, Winchester), and the ways to the Conversea (at Winchester Centre), were by some equivalent of present Main Street, or by a way through Pond. Cambridge and Church Streets (Winchester) — the last two being "Plain Street" and ** Driver's Lane." To Cross Street the way appears to be an old one in uae from the beginning of the first
Text read by machine from the scan; it may contain errors.
and in the same year the remaining portion of the town was divided into two parishes for religious purposeh — the First, or Old Parish, including the present territory of Woburn and Winchester, and the Second Parish, or Woburn Precinct, as it was often called, including the part later set off a.s the town of Burlington. Town-meetings after this period were often held alternately in each parish. This is evident from the
Text read by machine from the scan; it may contain errors.Scans and text from the Internet Archive. Books published in 1930 or earlier, which are in the public domain.
Weddings on Main Street, storms, parades, school pictures, the old store. If it’s in your family album, it belongs here.
Every edition of the U.S. Geological Survey’s map of Winchester. Tap a year, or press play to watch the town change.
U.S. Geological Survey historical topographic maps (public domain), via Esri’s collection of the scans. The red ring marks the center of Winchester.
Fire insurance maps drew every building, what it was made of and what it was used for, so insurers could price the risk of fire. Pick a year, then a sheet.
1894Sheet 1 of 6Sanborn Map Company, via the Library of Congress. Editions published in 1930 or earlier, which are in the public domain.
Grew from 1,353 people in 1850 to 22,970 in 2020, more than tenfold.
18 censuses, 1850–2020.
U.S. Census Bureau decennial counts, from the census table on Winchester’s Wikipedia page.
Writers, athletes, leaders and more, ranked by how widely they’re known.
Winchester’s post office has been open since 1850. Another post office, South Woburn, opened and closed inside today’s town.
US Post Offices dataset (Blevins & Helbock, CC0). Places and cemeteries from the USGS Geographic Names Information System (2021).
The first neighbors to add old photos shape how Winchester’s history is told.
Each neighbor’s History grade, on the same three inputs.
In 1640, according to Wikidata. Winchester’s post office opened in 1841, and the census of 1850 counted 1,353 people here.
Winchester is among the most historic 1% of U.S. towns, #18 of 283 in Massachusetts. The History grade combines the town’s founding era, the share of homes built before 1940 and its National Register listings. It’s a character grade, so it isn’t part of the overall grade. How it works.
67 listings: 62 buildings, among them the Capt. Josiah Locke House (listed 1979, the first), 4 historic districts with 422 contributing buildings, and 1 site. 507 historic buildings in all.
39% of Winchester’s homes were built before 1940 (Census estimate, ±4.1 points), against a typical 21% for a Massachusetts town; the median home was built in 1954.
What the archives can’t tell you, neighbors can.
Founding dates: Wikidata, Wikipedia, the U.S. post office records of Blevins & Helbock (CC0) and the Census. Homes by year built: Census ACS 2020–24. National Register of Historic Places: National Park Service (list of May 22, 2026). Old photos, postcards and papers: Wikimedia Commons, the Library of Congress and other public archives, credited on each item’s page. Maps: U.S. Geological Survey historical topographic maps (via Esri) and Sanborn fire-insurance maps (Library of Congress). History text and census tables: Wikipedia (CC BY-SA 4.0). Places that used to be: USGS Geographic Names Information System (2021).
From Wikidata (6), the National Register of Historic Places (67), Wikipedia, Wikidata and Wikipedia for famous people, U.S. Geological Survey historical maps, U.S. Census counts (via Wikipedia), the US Post Offices dataset (Blevins & Helbock), the USGS Geographic Names Information System, Sanborn fire insurance maps (Library of Congress) and old county and town histories (Internet Archive). Archive images are copied here with their credits and licenses, shown on each photo’s page. Refreshed monthly.
