Winona’s post office opened in 1860, and 7 of its places are on the National Register
More historic than 61% of U.S. towns · #41 of 100 in Mississippi. What drives it
Most of Winona was built recently: 6% of its homes predate 1940 and the median home dates from 1976. 7 places in town are on the National Register, among them two historic districts with 505 buildings between them. Below: 9 old photos and papers, maps from 1886 on, and the census since 1880.
Founding year: the first Winona post office (Blevins & Helbock, CC0). Wikidata: 1861.The full story ↓
History grade
What drives Winona’s History grade
On its age, its old homes and the National Register, Winona is more historic than 61% of U.S. towns, #41 of 100 in Mississippi. Its National Register listings hold the grade up; its share of homes from before 1940 pulls it down.
B
HistoryA character grade: shown, never part of Winona’s overall grade.
Mississippi towns list more on the Register than most of the country (a typical Mississippi town has 71.9 per 10,000 residents, the U.S. 2.4), so Winona’s 1,226 sits above most of its state (98% of Mississippi towns have fewer) while its 513 historic buildings outnumber those of 97% of U.S. towns.
How sure. Graded on any two of the three inputs instead, the letter would range from C to B+. The pre-1940 share is a Census survey estimate (±3.4 points). The founding year is the first post office, not a stated founding date; Wikidata’s 1861 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 Winona’s past
Read from the archive, the National Register and the record. The page puts what stands out first.
National Park Service, National Register of Historic Places. Photos from Wikimedia Commons, credited on each place’s page.
Every building
Winona, building by building, 1886–1925
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.
1886Sheet 1 of 1
Edition
Sheets
BrickWoodStone
Sanborn Map Company, via the Library of Congress. Editions published in 1930 or earlier, which are in the public domain.
People over time
Winona, census by census
Peaked at 6,177 in 1980; 4,505 people lived here in 2020.
15 censuses, 1880–2020.
U.S. Census Bureau decennial counts, from the census table on Winona’s Wikipedia page.
Middleton was a town that developed in the 19th century two miles west of Winona's present location. Some locals consider it the predecessor to Winona. After the railroad was built to the east of Middleton, development shifted to what became Winona, bypassing Middleton.
The first European-American settler in the area, which was originally part of Carroll County, was Colonel O.J. Moore, who arrived from Virginia in 1848. He agreed to the railroad being constructed through his property, and a station was built in 1860 near his plantation home.
Nothing in the archives for these yearsWeddings on Main Street, storms, parades, school pictures, the old store. If it’s in your family album, it belongs here.
The Winona post office opened in 1860, the earliest record of the town by name (U.S. post office records). Wikidata gives 1861.
How does Winona rank for history?
Winona is more historic than 61% of U.S. towns, #41 of 100 in Mississippi. 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 Winona?
7 listings: 5 buildings, among them the Wisteria Hotel (listed 1979, the first), and 2 historic districts, the Winona Commercial Historic District and the Winona Historic District, with 505 contributing buildings. 513 historic buildings in all.
How old are the homes in Winona?
6% of Winona’s homes were built before 1940 (Census estimate, ±3.4 points), against a typical 4.5% for a Mississippi town; the median home was built in 1976.
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 (8), the Library of Congress (7), Wikidata (1), the National Register of Historic Places (7), 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 and Sanborn fire insurance maps (Library of Congress). Archive images are copied here with their credits and licenses, shown on each photo’s page. Refreshed monthly.
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