Chestertown’s historic district, a National Historic Landmark, takes in 484 buildings
More historic than 98% of U.S. towns · #6 of 261 in Maryland. What drives it
14 places in town are on the National Register, among them the Chestertown Historic District, a National Historic Landmark, and two historic districts with 485 buildings between them. Below: 18 old photos and papers, maps from 1885 on, and the census since 1860.
Founding year: Wikidata. First post office: 1776.The full story ↓
History grade
What drives Chestertown’s History grade
On its age, its old homes and the National Register, Chestertown is more historic than 98% of U.S. towns, #6 of 261 in Maryland. All 3 inputs are above most U.S. towns; its National Register listings ranks highest and its share of homes from before 1940 lowest.
A+
HistoryA character grade: shown, never part of Chestertown’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 Chestertown’s 905 sits above most of its state (95% of Maryland towns have fewer) while its 506 historic buildings outnumber those of 97% of U.S. towns.
NoteThe founding year comes from Wikidata alone; no second source gives 1706.
How sure. Graded on any two of the three inputs instead, the letter would range from A to A+. The pre-1940 share is a Census survey estimate (±8.1 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 Chestertown’s past
Read from the archive, the National Register and the record. The page puts what stands out first.
The country’s official list of buildings and places worth saving. One is a National Historic Landmark, the highest tier. Boundary changes and added documentation are counted with their listing.
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.
Indigenous peoples have lived in what is now Chestertown for thousands of years. At the time of European colonization, the primary tribe on the Eastern Shore was the Nanticoke. In Nanticoke oral tradition, their ancestors migrated south from "the land of snow and ice" through the Ohio Valley and the Allegheny Mountains until they reached the Eastern Shore. The Nanticokes spoke an Algonquian language.
Passages that mention Chestertown, cut from the printed page as they were published.
History of Kent County, Maryland, 1630-19161916 · page 155Read the page →
Read the text
History of Kent County, Maryland 155 erected and a church built for that parish at the present site of Christ Church "I. U." Its "Chapel of Ease" was built at Chestertown where the present Emmanuel Church now stands. It is authoritatively stated that the chapel at Chestertown was made the "church" of Chester parish about the year 1809, "I. U." becoming the "Chapel of Ease."
Text read by machine from the scan; it may contain errors.
History of Kent County, Maryland, 1630-19161916 · page 96Read the page →
Read the text
Fifteen years after the Christmas conference, in 1784, the Methodists of Kent, who had increased wonderfully in numbers and influence, especially in Chestertown and the region round about, resolyed to construct a house of worship in Chestertown. In endeayoring to secure a grant of land on the public square in a day before this stone of Methodism, which the builders rejected, had become the head 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.
Timeline
Chestertown, 1706 to 1970
Woven from the archive, old maps, post office records, the National Register and the people born here.
Every edition of the U.S. Geological Survey’s map of Chestertown. Tap a year, or press play to watch the town change.
1901Chestertown sheet · 1:62,500
U.S. Geological Survey historical topographic maps (public domain), via Esri’s collection of the scans. The red ring marks the center of Chestertown.
Every building
Chestertown, building by building, 1885–1915
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.
In 1706, according to Wikidata. Chestertown’s post office opened in 1776, and the census of 1860 counted 1,539 people here.
How does Chestertown rank for history?
Chestertown is more historic than 98% of U.S. towns, #6 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 Chestertown?
14 listings: 11 buildings, 2 historic districts, the Chestertown Historic District and the Lauretum, with 485 contributing buildings, and 1 structure. 506 historic buildings in all.
How old are the homes in Chestertown?
22% of Chestertown’s homes were built before 1940 (Census estimate, ±8.1 points), against a typical 3.3% for a Maryland town; the median home was built in 1982.
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 (14), 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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