Each edition grades its towns against each other only.
More historic than 82% of U.S. towns · #389 of 758 in New York. What drives it
2 places in town are on the National Register. Below: 1 old photo or paper, maps from 1884 on, and the census since 1850.
Chester dates its founding to 1721 (Wikidata). The census first counted it in 1850.
More historic than 82% of U.S. towns, on its age, its old homes and the National Register.
On its age, its old homes and the National Register, Chester is more historic than 82% of U.S. towns, #389 of 758 in New York. All 3 inputs are above most U.S. towns; its age ranks highest and its share of homes from before 1940 lowest.
New York towns list more on the Register than most of the country (a typical New York town has 12.3 per 10,000 residents, the U.S. 2.4), so Chester’s 12.4 sits near the middle of its state (50% of New York towns have fewer) while its 5 historic buildings outnumber those of 70% 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 first neighbors to add old photos shape how Chester’s history is told.
Woven from the archive, old maps, post office records, the National Register and the people born here.
Born hereWilliam Terry Jackson is born here
On the mapFirst mapped by the U.S. Geological Survey
In the archiveGlenmereEvery edition of the U.S. Geological Survey’s map of Chester. 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 Chester.
From Wikipedia’s history of Chester.
The Lenape people have settled in Orange County for over 5,000 years. Europeans first settled in the 1700s which were ethnic Dutch and English colonists.
Text from Wikipedia, licensed CC BY-SA 4.0.
Passages that mention Chester, cut from the printed page as they were published.
b. 12, 19. 1870. in Lancaster Co., Pa. (ii) Chester Baily, b. 8, 8. 1872, in Chester Co., Pa. ; d. there, 8, 25. 1873. ( iii) Pierce Webb, b. 10. 25. 1873, i" Lancaster Co.. Pa. (iv) Martha Jane, b. i, 25.
Text read by machine from the scan; it may contain errors.
at Hamorton. Chester Co., Pa., 4, 29, 1843; d. at Philadelphia, 4, 6. 1895: bur. in Oakland Cemetery, \\'est Chester, Chester Co.: m. at her father's home in East Bradford Twp.. that county, 10, 6, 1869, Ellen Brinton Entrekin (Friend), b.
Text read by machine from the scan; it may contain errors.
David Townsend (17S7-lsr.M. Botanist. Born at Pughtown; 1810, appointed clerk in office of Regisl i and Recorder of Chester county; 1813. elected Commissi re r of Chester county: 1814, one of original Directors of National Bank of Chesinty; 1817 to 1S49, Cashier of
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.
One decade in the archive so far: the 1920s. Scroll each row; tap a photo for its story.
2010Sugar Loaf, New York
2010Sugar Loaf, New York
2010Sugar Loaf, New York
2010Sugar Loaf, New York
2010Sugar Loaf, New York
2010Sugar Loaf, New York
2010Chester, New York
2010Chester, New York
2009NY 17M at Brookview Farm
2009Chester, New York
2009Chester, New York
2009Chester, New York
2009Chester, New York
2009Chester, New York
2009Chester, New York
2009Chester, New York
2009Chester, New York
2009Chester, New York
2009Chester, New York
2009Chester, New York
2008Fury Brook Farm
2007Yelverton Inn
2007First Presbyterian Church ofFire 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.
1884Sheet 1 of 1Sanborn Map Company, via the Library of Congress. Editions published in 1930 or earlier, which are in the public domain.
No then-and-now pairs yet. Take a photo from the same spot as an old one and they appear here side by side.
Find the spot, match the angle, and add your photo. It becomes the first then-and-now pair on Chester’s page.
Retake this view · +15The 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.
Grew from 1,641 people in 1850 to 12,646 in 2020, 7 times over.
18 censuses, 1850–2020.
U.S. Census Bureau decennial counts, from the census table on Chester’s Wikipedia page.
Each neighbor’s History grade, on the same three inputs.
In 1721, according to Wikidata. Chester’s post office opened in 1797, and the census of 1850 counted 1,641 people here.
Chester is more historic than 82% of U.S. towns, #389 of 758 in New York. 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.
13% of Chester’s homes were built before 1940 (Census estimate, ±8.2 points), against a typical 27% for a New York town; the median home was built in 1981.
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 Wikimedia Commons (24), Wikipedia, Wikidata and Wikipedia for famous people, U.S. Geological Survey historical maps, U.S. Census counts (via Wikipedia), 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.
