Listening / Travel & Tourism / Chasing the Headless Horseman
Chasing the Headless Horseman
The History, Hijinks, and Halloweens of the Real Sleepy Hollow
- Written by
- J.W. Ocker
- Read by
- Dustin Naylor
- Length
- 9 hrs 8 min
- Rating
- 5.0 / 5
- Publisher
- Tantor Media
- Released
- 2026-09-29
Shelved under
What it is
A spirited look at Sleepy Hollow's haunted corners, local lore, and its connection to one of America's most famous ghost stories.
National bestselling and Edgar Award–winning travel writer J. W. Ocker investigates the town that inspired Washington Irving's famous short story, "The Legend of Sleepy Hollow." Ocker dives into the storied history of the Headless Horseman's stomping grounds, visiting the village's graveyard where Irving himself is buried and exploring all the present-day spookiness of one of the strangest towns in the country.
Blending travelogue, cultural criticism, and behind-the-scenes reporting, Ocker uncovers the tensions between tourism and tradition, profit and preservation, fiction and fact. With wit and curiosity, Chasing the Headless Horseman tells the story of how one small town reinvented itself as America's Halloween capital, complete with statues, street signs, and an eighteen-foot-tall Headless Horseman. A must-listen for anyone who loves ghost stories, Halloween, or small-town drama, Ocker's new book does for Sleepy Hollow, New York, what his A Season with the Witch did for Salem, Massachusetts.
On the charts
Last charted October 3, 2026. Its best position was 1 on New releases in Travel & Tourism, reached September 30, 2026. Seen on 4 charts over 4 days of readings, the first on September 30, 2026.
| Chart | Best | Days | Last seen |
|---|---|---|---|
| Travel & Tourism | |||
| New releases | 1 | 4 days | October 3, 2026 |
| Bestsellers | 2 | 3 days | October 2, 2026 |
| Apple Books | 10 | 3 days | October 3, 2026 |
| History | |||
| New releases | 7 | 2 days | October 2, 2026 |
If you liked this
- A Season with the Witch J.W. Ocker Tom Beyer14 hrs 58 minunrated More by J.W. Ocker Where to buy
- Call of the Dead Serena Valentino VillainsBook 13 5 hrsunrated Also about sleepy and hollows Where to buy
- Ghosts of Salem Sam Baltrusis David de Vries3 hrs 30 minunrated Also about ghosts Where to buy
- Hawaiian Myths, Gods, and Legends Ocean Breeze Adventures Robert Dale Brown jr4 hrs 39 min5.0 (16) Also state & local Where to buy
- The Only Plane in the Sky (Revised and Expanded Edition for the 25th Anniversary) Garrett M. Graff, Holter Graham A Full 45-Person Cast18 hrs 7 min4.9 (3,105) Also state & local Where to buy
- The Boys in the Boat Daniel James Brown Edward Herrmann14 hrs 24 min4.8 (43,776) Also state & local Where to buy
- The Gales of November John U. Bacon Johnny Heller10 hrs 53 min4.8 (1,490) Also state & local Where to buy
- MeatEater's American History: The Mountain Men (1806-1840) Steven Rinella MeatEater's American HistoryBook 2 Steven Rinella7 hrs 32 min4.8 (948) Also state & local Where to buy
More in Travel & Tourism
The whole shelf →- Zen and the Art of Motorcycle Maintenance Robert M. Pirsig Zachary Quinto12 hrsunrated Where to buy
- Travel Beyond the Landmarks: Discovering Authentic Places Through Local Culture and Everyday Life Skylar Robson S. L. Powell32 minunrated Where to buy
- One Man In Christian Craighead Christian Craighead5 hrs 26 min4.9 (534) Where to buy
- Learn Spanish with Paul Noble for Beginners – Complete Course Paul Noble Paul Noble13 hrs 21 min4.8 (1,470) Where to buy
- The Yacht Kayte Nunn Beth Lilly8 hrs 27 min4.2 (1,998) Where to buy
- New England's Unexplained Mysteries: Ghosts, UFOs, Cryptids, & More (Unexplained Encounters) Tony Urban Unexplained Encounters Benjamin Hunter3 hrs 37 minunrated Where to buy
- Into the Wild Jon Krakauer Philip Franklin7 hrs 5 min4.4 (10,739) Where to buy
- High Erika Fatland Samantha Desz20 hrs 15 minunrated Where to buy















