Each edition grades its towns against each other only.
More historic than 87% of U.S. towns. What drives it
1 place in town is on the National Register. Below: 6 old photos and papers from 1778 on and old-book passages.
The Pawling post office opened in 1828, the earliest record of the town by name.
More historic than 87% of U.S. towns, on its age, its old homes and the National Register.
On its age, its old homes and the National Register, Pawling is more historic than 87% of U.S. towns. All 3 inputs are above most U.S. towns; its share of homes from before 1940 ranks highest and its National Register listings 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 Pawling’s 20.0 sits near the middle of its state (56% of New York towns have fewer) while its 4 historic buildings outnumber those of 68% of U.S. towns.
Founding year: the first post office (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.
Woven from the archive, old maps, post office records, the National Register and the people born here.
In the archiveDetail of 1778 Erskine Map of Quaker Hill
In the archiveOld Quaker Meeting House, erected 1764
In the archiveHolmes-NY-postcardWikipedia doesn’t have a history of Pawling yet. The photos, dates and memories neighbors add here are how it gets written.
Its first post office opened in 1828. Between the 2010 and 2020 censuses its population fell from 2,347 to 1,995 (-15%).
Passages that mention Pawling, cut from the printed page as they were published.
The sheriff's list of landowners in the county in 1740, does not cpntain the names of the Quakers who formed a little community at Quaker Hill in the present town of Pawling, begun in 1730. Benjamin Ferris and Nathan Birdsall were here as early as 1728, coming from the town of Rye, Westchester county. Between the years 1730 and 1740, the tide of emigration was brisk to this fertile section of the county. Among those who arrived at that period are found the names of Aiken, Irish, Wing, Taber, Osbom, Briggs, Hoag, Dakin,
Text read by machine from the scan; it may contain errors.
approximately that which was afterwards known as the Willis Line, or the line advocated by some for the division line when Putnam County was taken off in 1812. This hne was run through what is now the incorporated limits of the village of Pawling, and is thus described: "Beginning on the Oblong line at a large heap of stones set up which bears north 25 degrees, west 38 links from a large rock on which are cut the letters H. B., B. B,-, and P. P. ; a new house built by Adam Chase bears the same course that the rock does. From
Text read by machine from the scan; it may contain errors.
in I ihe arrival of Father Tandy as charge of affairs in the rearrangement of the missions, we begin now to tell more specifically of the beautiful village of Pawling, pleasantly situated sixty miles north of Greater New York. Father Orsenego, yielding the northern part of his extensive charges from fatigue and overwork, brought his closer attention to the spiritual wants nf the people nearer to him, namely, those in Brewster, Katonah, Lake Mahopac
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.
3 decades in the archive, from the 1770s to the 1910s. Scroll each row; tap a photo for its story.
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 Pawling’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.
Nobody well known was born in Pawling itself, so here are the best known from just nearby.
Most archives stop around 1920. The photos from after that are in family albums, not libraries.
The Pawling post office opened in 1828, the earliest record of the town by name (U.S. post office records).
Pawling is more historic than 87% of U.S. towns. 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.
31% of Pawling’s homes were built before 1940 (Census estimate, ±8.5 points), against a typical 27% for a New York town; the median home was built in 1957.
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 (5), the Library of Congress (1) 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.
1909
1914
1914