Princess Anne dates to 1733, and 8 of its places are on the National Register
More historic than 84% of U.S. towns · #26 of 261 in Maryland. What drives it
Most of Princess Anne was built recently: 4% of its homes predate 1940 and the median home dates from 2000. 8 places in town are on the National Register, among them two historic districts with 250 buildings between them. Below: 4 old photos and papers, maps from 1894 on, and the census since 1870.
Founding year: Wikidata. First post office: 1792.The full story ↓
History grade
What drives Princess Anne’s History grade
On its age, its old homes and the National Register, Princess Anne is more historic than 84% of U.S. towns, #26 of 261 in Maryland. Its age holds the grade up; its share of homes from before 1940 pulls it down.
A−
HistoryA character grade: shown, never part of Princess Anne’s overall grade.
Few Maryland towns list much on the Register (a typical Maryland town has 0.9 per 10,000 residents, the U.S. 2.4), so Princess Anne’s 745 sits above most of its state (93% of Maryland towns have fewer) while its 266 historic buildings outnumber those of 95% of U.S. towns.
NoteThe founding year comes from Wikidata alone; no second source gives 1733.
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 (±4.1 points).
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 →
What stands out about Princess Anne’s past
Read from the archive, the National Register and the record. The page puts what stands out first.
The town at the head of the Manokin River was named for Princess Anne of Great Britain, daughter of King George II. Established in 1733, it serves as the county seat for Somerset County, the southernmost county in Maryland.
In the mid-18th century, the town became a market center based on the river trade and development of tobacco plantations in the area. Enslaved African Americans were used to cultivate and process this labor-intensive crop, in addition to other farming. The town's trade was augmented by the southward extension of the Eastern Shore Railroad on Maryland's Eastern Shore. At that time, the Manokin River was navigable as far as the bridge at Princess Anne.
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.
Every edition of the U.S. Geological Survey’s map of Princess Anne. Tap a year, or press play to watch the town change.
1942Princess Anne sheet · 1:24,000
U.S. Geological Survey historical topographic maps (public domain), via Esri’s collection of the scans. The red ring marks the center of Princess Anne.
Every building
Princess Anne, building by building, 1894–1911
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 1
Edition
Sheets
BrickWoodStone
Sanborn Map Company, via the Library of Congress. Editions published in 1930 or earlier, which are in the public domain.
Then & now
Stand where they stood
No then-and-now pairs yet. Take a photo from the same spot as an old one and they appear here side by side.
Retake this viewMaryland - Point of Rocks through Salisbury, 1917
Find the spot, match the angle, and add your photo. It becomes the first then-and-now pair on Princess Anne’s page.
Princess Anne’s post office has been open since 1792.
Gone or out of use
Manokin Bridgebridge
1cemetery inside Princess Anne
Antioch Methodist
US Post Offices dataset (Blevins & Helbock, CC0). Places and cemeteries from the USGS Geographic Names Information System (2021).
Questions about Princess Anne’s history
What year was Princess Anne founded?
In 1733, according to Wikidata. Princess Anne’s post office opened in 1792, and the census of 1870 counted 805 people here.
How does Princess Anne rank for history?
Princess Anne is more historic than 84% of U.S. towns, #26 of 261 in Maryland. 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 Princess Anne?
8 listings: 6 buildings, among them the Teackle Mansion (listed 1971, the first), and 2 historic districts, the Princess Anne Historic District and the University of Maryland Eastern Shore, with 250 contributing buildings. 266 historic buildings in all.
How old are the homes in Princess Anne?
4% of Princess Anne’s homes were built before 1940 (Census estimate, ±4.1 points), against a typical 3.3% for a Maryland town; the median home was built in 2000.
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 (18), the National Register of Historic Places (8), 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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