Headless Horseman Rides Again, This Time For Charity

BENNINGTON – The Headless Horseman, or “The Hessian”, has been the stuff of nightmares for almost 200 years. But the Sleepy Hollow rider says his ghouling days are long past.

Having relocated to Bennington area in the 1970’s, the decapitated horseman, who now goes by Bill Hessian, lives in a quaint cabin on the edge of the Green Mountain National Forest. “There’s just so much more room here for me and my horse, Mr. Bones” Hessian says about the decision to move to Vermont, “Plus the people here love Halloween. I can walk around downtown the whole month of October and get high fives from people because they think it’s just an awesome costume.”

While Hessian, or “The Hess” to his friends, spent the 200 years following the American Revolution looking for his lost head. He says the last 150 of those years were pretty dark “You know, the first 50 years I was really just looking for my head I mostly left people alone. Then the book about me came out and all the sudden there are Headless Horseman hunting parties and people wielding torches. I got bitter, and yeah, I took a few peoples’ heads but I was in a really dark place. I regret those days”

With the move to Vermont Hessian says he feels like he’s been given a new lease on life, again. “A lot of those years I felt like I had lost a piece of myself. When I moved to Bennington area in October of ‘73 everyone was so welcoming and through their warmth I learned to accept that head or not, I was whole.”

To give thanks to the city he loves Hessian spends the entire month of October entering Bennington area costume contests, donating all of his winnings to local charities. Unsurprisingly he wins a lot.

“Bill! The Hess! That guy has been coming in the same costume for almost…fifty years? That can’t be right. Anyway, no one can come close to the quality he presents,” says Bennington High School principal and Halloween costume contest judge Bob Crane. Mr. Crane confirmed that “The Hess” has never accepted any prize money and instead directs the contest organizers to donate any winnings to a local children’s charity. “He’s a class act who really cares about the kids” Crane added, “It’s nice to know there are still a few people out there with their heads on straight.”

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