Cumberland Gap’s post office opened in 1803, and 25% of its homes were built before 1940
1 place in town is on the National Register, among them a historic district with 34 buildings. Below: 3 old photos and papers, maps from 1891 on, and the census since 1910.
The Cherokee and Shawnee Native American tribes traveled through a game trail known to the Shawnee as Athiamiowee. The tribes often fought each other and white settlers called the trail The Warriors' Path. The area that came to be known as the Cumberland Gap was a gateway on the trail through the mountains. Although many settlers had traveled through the pass and their reports had traveled back east, Thomas Walker is credited as the settler who discovered the pass. Walker was hired by the Loyal Land Company to search for a suitable site for a settlement on the western side of the mountains. It became a postal town in 1803, and was officially incorporated as a city in 1907.
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 Cumberland Gap. Tap a year, or press play to watch the town change.
1927Middlesboro 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 Cumberland Gap.
Every building
Cumberland Gap, building by building, 1891–1913
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.
1891Sheet 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 viewView of Cumberland Gap, from the south, 1862
Find the spot, match the angle, and add your photo. It becomes the first then-and-now pair on Cumberland Gap’s page.
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). How TownRatings grades history →
From Wikimedia Commons (9), the Library of Congress (3), the National Register of Historic Places (1), 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.