If you are like me when you think of The Headless Horseman your mind may immediately go to the Disney classic The Adventures of Ichabod and Mr. Toad where a segment features the ominous figure chasing after poor Ichabod. However this mythical figure had roots that go back centuries appearing in folklore around Europe since the Middle Ages. The figures traditionally depict a rider upon horseback who is missing their head. Depending on the legend, the Horseman is either carrying his head, or missing it altogether, and may be searching for it.
To help us celebrate the spooky season, elongated coin designer Amy Brennan has released her latest Halloween themed coin. This time featuring The Headless Horseman, with a dead creepy tree and some tombstones in the background and the phrase “Heads will Roll”.
This is another fantastic design from Amy. I enjoy all her designs but these Halloween themed ones have a very special place in my collection and I look forward to them each year. If you are interested in acquiring one of these for your own collection, she can be reached through her Facebook group Pressed Penny Mafia – PPM.
Stay Spooky and as always Keep on Pressing!!

Pingback: Top Voted Privately Designed Coin 2025 | David's Coin Travels