The Headless Horseman cards.
updated Aug 28, 2026
Every The Headless Horseman card we price, most valuable first. Prices are what copies actually sold for, updated daily.
2The Headless Horseman - Terror of Sleepy HollowWhispers in the Well · 125/204$18.69
1The Headless Horseman - Terror of Sleepy Hollow (Enchanted)Whispers in the Well · 232/204$264.27
3The Headless Horseman - Cursed RiderWhispers in the Well · 174/204$1.21$264.27▲0.2%The Headless Horseman - Terror of Sleepy Hollow (Enchanted)WHISPERS IN THE WELL$18.69▼-5.3%The Headless Horseman - Terror of Sleepy HollowWHISPERS IN THE WELL$1.21▲2.5%The Headless Horseman - Cursed RiderWHISPERS IN THE WELL
$0.26–The Headless Horseman - Relentless SpiritWHISPERS IN THE WELLWhat a The Headless Horseman card is worth
The most valuable The Headless Horseman on this list is The Headless Horseman - Terror of Sleepy Hollow (Enchanted) from Whispers in the Well at $264.27, and the 4 priced copies across 1 sets are worth $284 together. Most of that sits in a handful of printings: the older the set and the scarcer the print run, the wider the gap to the rest.
The highest PSA 10 on record for The Headless Horseman sold for $551.30.
If you are trying to identify which The Headless Horseman you have, the set name is printed on the card and the collector number sits in the bottom corner. Open the card here and the page carries every printing of it, the graded prices, and whether grading the copy is worth the fee. Sets to start with: Whispers in the Well.