Oct 27 2015

Halloween is this Saturday night, so here's a little something spooky and mysterious... The painting below by Jenny Joyce hangs at the Gearhart Hotel on the coast. It depicts an old town tradition, in which a headless horseman rode through town scaring kids every Halloween. But who was it, exactly? Well, the headless horseman may actually have been a headless horsewoman. But no one seems to know for sure.

Read a few excerpts of emails that Tim Hills has received and interviews that he did with town residents about the legendary nighttime rider.

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"Dear Tim: I recently became aware of the Jenny Joyce painting of the Headless Horseman at the Gearhart Sand Trap restaurant. I had not known that when I rode as the Headless Horseman in Gearhart in the ‘60s, it would become a ‘legend' worthy of a painting hanging in a McMenamins restaurant 50 years later!

I am interested in your research of this subject. I know of the article and picture of the Headless Horseman in the Seaside Signal since I'm the one who put them there (I worked for the Signal at the time). But the information that there was a headless horseman riding in the 1950s I believe to be wrong. I was a child in that time period living in Gearhart, riding my horse everywhere and knowledgeable of most horse-type activities. I never heard of a horseman riding in that decade. My husband, born in Gearhart, trick-or-treating in the 1940s and 50s, never heard of or saw a headless horseman either. I believe that my rides in the 1960s were the only rides of the Headless Horseman until that time."- Nancy Cheney Brown, 2013

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"Dear Tim: My mother, Fern Beeman, was the headless horseman of Gearhart. During the ‘40s and ‘50s, she would pull a black shirt up over her head, mount her black Morgan horse, and gallop throughout town terrorizing all of the Halloweeners! She did this for years and no one knew who the horseman was." - Jake Jacobsen, 2008

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From an interview with the Osburn family in 2008, who owned and operated the old Gearhart Hotel through the 1960s. They also had a stable of horses that could be rented for beach rides, etc. Jon B = John Blissett (cousin to the Osburns)

Q: Another great story I heard about was the Halloweens where the Headless Horseman ran through town.
Jon B: That was me. Not at first. I think the first one was Ted Klee.
Jim: Yeah, Ted. Then you, and then me.
Jon B: And I did it, I came home from college, and Elaine, Burr's mother, was talking about somebody keepin' the thing going. The uh... tradition going, and she said, "Jon, you, you're gonna be the Headless Horseman!" I said, "Baloney! You don't have a horse I could ride!" "Oh yeah, yeah, you can ride that thoroughbred. You can ride the thoroughbred." ‘Clarion' or some freakin' thing.
Jan: Did it get rid of you, Jon?
Jon B: Oh, no! But damn near! Those kids were throwin' water balloons at me and all this stuff, and I said, "Boy, that's enough for me." Another woman that did it before me too, was Nancy Cheney. Nancy Cheney. She did it.
Blake: Mom never did it?
Jon B: No, your mom never did it.
Q: See, everyone I've talked to thinks it was your mom.
Jon B: Elaine?
Q: Yeah.
Burr: [unintelligible,01:1Jan:38]. [Tim laughs] She was smarter than that.
Jim: I did it two years, and that was enough for me, too.
Q: You guys scared the hell out of a lot of people, that's what I've heard.
Jon B: Oh yeah! It was fun!
Jim: But they get down in the bushes and they just wait for you! [Tim laughs] Right along Ridgepath, you were in trouble. I mean, you had water balloons comin' both ways, and... Yeah, I did a couple years. ... And then, the cops told me I couldn't do it anymore.
Q: Really?
Jim: Yeah!
Q: Why?
Jim: Oh, we got this new Gearhart cop. I didn't have tail lights.
Q: [cracking up] Are you serious?
Jim: I'm serious! Didn't have tail lights! And I said, "Tail lights, I don't even have headlights!" [all laughing] I said, "The horse knows where he's goin'!"

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From an interview with childhood friends and Gearhart residents Sally Valade and Steve Earle in 2007; they were also close friends with the Osburn kids and helped out in their stables:

SV: ...every... October, we would take the horses and put up the tack and take them out to the pasture! Halloween was like the last possible day that you could be able to put them out there.
SE: ‘Cause storms like this had started happening.
SV: Yeah. Right. And so, you didn't want to really take any chances. You wanted to get it out there, but... Elaine [Osburn] always kept one of - or two of her best thoroughbreds in the barn all year round. ‘Cause she would jump and show, and... whatever. And, so, Halloween, we, in Gearhart, it wasn't like today where the parents take the kids around from door to door. It was "Here's your bag, here's your costume, see you later, we're going to a party." And, the parents would go to their parties, and we would go around... And pretty soon, you'd have a herd of 30 kids running around together, because you'd hook up with everybody, and then... It was just wide open! And, so, Elaine would get - well, we never knew for sure. We always suspected that it was Elaine, but we could never prove it. But she had this costume that literally was a headless, black... with a cape, and the whole - I mean, the black boots, the cape, everything. And she and this big, uh - like a cane, but not - it had a [unintelligible] to it.
SE: I didn't know about this.
Q: You didn't at all?
SE: No.
SV: And she would get on her horse, and she had, you know, flashing lights, flash lights, and she would flash them like, you know, that, and she would ride at a gallop, ‘cause she was one hell of a horseman! And she would ride at a gallop through town, and just absolutely scare the shit out of all of us kids! [Tim and Steve laugh] We'd see her coming, and we would... you know, we'd see the headless horseman, and we would... go hide, and then, you know, and she'd buzz the hotel, and run through the parking lot, and run across the golf course, and um... And up and down Gin Ridge, and up and down Marion Avenue, and down through Gearhart, and... you know, [unintelligible], and then be gone in the darkness! And, nobody ever knew who she was! I mean, that it was her, and we couldn't prove it, and she would never own up to it ...

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