Founding year: the first Middletown post office (Blevins & Helbock, CC0). Wikidata: 1848.The full story ↓
History grade
What drives Middletown’s History grade
On its age, its old homes and the National Register, Middletown is more historic than 86% of U.S. towns, #325 of 758 in New York. All 3 inputs are above most U.S. towns; its share of homes from before 1940 ranks highest and its National Register listings lowest.
A
HistoryA character grade: shown, never part of Middletown’s overall grade.
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 Middletown’s 5.6 sits near the middle of its state (37% of New York towns have fewer) while its 17 historic buildings outnumber those of 79% of U.S. towns.
How sure. Graded on any two of the three inputs instead, the letter would range from B+ to A. The pre-1940 share is a Census survey estimate (±3.3 points). The founding year is the first post office, not a stated founding date; Wikidata’s 1848 falls in the same era, so the grade doesn’t depend on which one is used.
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 →
What stands out about Middletown’s past
Read from the archive, the National Register and the record. The page puts what stands out first.
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.
John Green purchased land from the DeLancey patent and probably settled the area around 1744. Due to its location between other settlements, residents adopted the name of Middletown, changing it later to South Middletown to avoid confusion with a nearby location. Eventually they dropped the word "south", using the current name when the community became a village in 1848. The village was incorporated as a city in 1888.
The First Congregational Church of Middletown, established in 1785, has the highest spire downtown. Construction of its first building was a sign of Middletown becoming established as a village. Its current church building was constructed in 1872.
the stock was sold. The New York, Ontario & Western Railway Company was organized and took over the property of the old New York & Oswego Midland Railroad ("ompany. As a result of the construction of this road, to which the town of Wallkill and city of Middletown have contributed so largely, the railroad shops were located at Middletown, which brought a very large infiux to the population of the town and city, and added largely to their taxable value. It also resulted in building the road from Middletown to Cornwall, and the extension of what was known as
Text read by machine from the scan; it may contain errors.
The history of Orange County, New York1908 · page 329Read the page →
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town, was of such little importance that historians declined to mention it, yet this stream, 1\ ing practically all in the town, was at one time the scene of five thriving saw-mills in operation, but which have since disappeared. Yet the city of Middletown in i8()0 saw a basis of great water works in this stream, and just from the line at the headwaters of this kill in the town of W'allkill, erected a reservoir which was known as Highland Lake, containing about 500,000,000 gallons of water. On April 22, 1901, just below Highland Lake and in the town of Mount Llope, the city of
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The chronicles of Middletown, containing a compilation of facts, biographical sketches, reminiscences, anecdotes, &c., connected with the history of one of the oldest towns in Pennsylvania1906 · page 152Read the page →
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Philadelphia, will naturally accrue, and that is, instead of great quantity of produce of dififerent kind being carried from the counties of York and Cumberland to the town of Baltimore, they will be carried through the channel of the town of Middletown to the city of Philadelphia. "It may not be improper to observe that Middletown is situated at the very lowest end of navigable water of said river Susquehanna, so that the trade of that extensive river will at all events centre in that town and be carried from thence to the city of Philadelphia, and conse-
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and ran a schooner in the West India trade. While in the West Indies he contracted the yellow fever. He recovered, but thereafter abandoned a sea-faring life. In May, 1803, he removed with his family from Middletown to the Berkshire :Mountains, and bought a place situated about a mile and a half west of the village o'f Stockbridge, Mass. This place he afterward sold, and purchased a farm on the west margin of the mountain lake, of clear, deep water, one mile wide and two miles long, at the upper
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.
Timeline
Middletown, 1816 to 1983
Woven from the archive, old maps, post office records, the National Register and the people born here.
Middletown’s post office has been open since 1816.
Hamlets and corners on the map
Deer Run
Gone or out of use
Albert Street Public SchoolschoolFirst Presbyterian ChurchchurchLiberty Street Public SchoolschoolPublic School Number 8schoolStarhaven AirportairportWebb Horton Memorial Presbyterian Churchchurch
2cemeteries and burying grounds inside Middletown
HillsideSaint Joseph
US Post Offices dataset (Blevins & Helbock, CC0). Places and cemeteries from the USGS Geographic Names Information System (2021).
Help out
Finish Middletown’s story
Most archives stop around 1920. The photos from after that are in family albums, not libraries.
Decades since 1900 with photos
00s10s20s30s40s50s60s70s80s90s
0 of 10 decades. The empty ones are waiting for someone’s album.
The Middletown post office opened in 1816, the earliest record of the town by name (U.S. post office records). Wikidata gives 1848.
How does Middletown rank for history?
Middletown is more historic than 86% of U.S. towns, #325 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.
What is on the National Register in Middletown?
11 listings: 9 buildings, 1 site, and 1 structure. 17 historic buildings in all.
How old are the homes in Middletown?
33% of Middletown’s homes were built before 1940 (Census estimate, ±3.3 points), against a typical 27% for a New York town; the median home was built in 1960.
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), Wikidata (1), the National Register of Historic Places (11), 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.
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