The Haunted Chester InnSouthern Ghost Story and Appalachian Folklore
Origin
The Chester Inn was built by Dr. William Chester as a frontier stop along the Great Stage Road - the main route through East Tennessee before railroads. Known as "the finest inn on the Western Frontier," it welcomed countless travelers, politicians, and soldiers, including President Andrew Jackson, who lodged there during his early military years.
The building survived fires, wars, and the slow crawl of centuries. But the stories say not everyone checked out. Some tell of a tragic fire that once swept the upper floors, where the laughter of children was last heard. Others whisper that certain guests - particularly a tall man in old boots and a long coat - still walk the halls as if waiting for their carriage.
They say if you walk past the Chester Inn after dark, you can hear the boards creak like somebody’s pacing upstairs. Folks say a child’s laughter sometimes drifts down from the second floor, and every so often, a shadow crosses the window that ought to be empty.
Notes
One story claims that on quiet autumn nights, a deep voice says "Good evening, sir" near the front door - polite, formal, and unmistakably old-fashioned. Folks figure if it’s not Dr. Chester greeting you, it’s Andrew Jackson himself.
Legacy
Today the Chester Inn is a Tennessee State Historic Site and museum, open by day to tell Jonesborough’s early history - and by night, to tell its ghost stories. The blend of truth and tale has made it one of Appalachia’s best-loved haunts, where the frontier past still lingers just a breath away.
Every October, as the leaves turn and the air cools, Jonesborough’s storytellers gather out front to remind folks that even the oldest walls remember - and sometimes, they answer back.
Kin Topics
Related Pages
- Folklore: Bell Witch Cave - Tennessee Ghost Story and Southern Folklore
- Folklore: Mothman - Appalachian Folklore and West Virginia Legend
- Folklore: The Bell Witch - Famous Southern Ghost Story and Folklore
- Folklore: Wampus Cat - Appalachian Monster and Southern Folklore
- Folklore: White Screamer - Tennessee Legend and Southern Folklore
How to Cite This Page
- APA (7th edition)The Hillbilly Dude. (2025, October 24). The Haunted Chester Inn
Southern Ghost Story and Appalachian Folklore . HillbillySlang.com. https://www.hillbillyslang.com/folklore/the-haunted-chester-inn-jonesborough-tennessee - MLA (9th edition)"The Hillbilly Dude." "The Haunted Chester Inn
Southern Ghost Story and Appalachian Folklore ." HillbillySlang.com, 24 Oct. 2025, https://www.hillbillyslang.com/folklore/the-haunted-chester-inn-jonesborough-tennessee. - Chicago (17th edition)The Hillbilly Dude. "The Haunted Chester Inn
Southern Ghost Story and Appalachian Folklore ." HillbillySlang.com. October 24, 2025. https://www.hillbillyslang.com/folklore/the-haunted-chester-inn-jonesborough-tennessee.
Dislaimer
What you're reading here is old Southern folklore and storytelling - not medical advice, and not meant to guide health, or pregnancy decisions (especially pregnancy decisions!). These tales are part of how folks once made sense of the world, passed down from grandparents and midwives.
If you have any medical questions or concerns, talk with a qualified healthcare professional.
Learn more on the Folklore hub page.


