It’s not as classic an image as his 1858 painting, mostly because it doesn’t feature the Headless Horseman. 12 years,19 toons and still no HH mount! 11 Likes. The Horseman’s Reins are only going to be found inside of the Loot-Filled Pumpkin.You left out the Headless Horseman’s Night Charger which is dropping.Headless Horseman's Mount Unlike the Raven Lord, this is a very cool mount because despite of it's looks at first glance, this horse actually scales with your riding skill. Sinister Squashling's and the Hallowed Helm can drop off the Headless Horseman as well be a very rare Trick or Treat from an Innkeeper. The death spell, Headless Horseman, deals 530-590 base damage. (Obtaining this mount gives a Feat of Strength achievement.