Sean Mayo is a 54-year-old trans woman living in Burlington, Vermont.

The first time I hopped a freight train any distance was on my seventeenth birthday, February 24, 1987. Me and my friends had tried to drive up from the Grateful Dead shows in San Francisco to Canada to sell LSD, but the car crapped out. We hitchhiked back to Portland, Oregon from Hazel Dell, Washington and all got jobs at the Magic Kingdom on Ice selling snow cones, and occasionally LSD.

I was with my friend Doug, the son of the head of public relations for Union Carbide. He was a little street rat. He wore a pork pie hat. He was adorable. The first time I met him was on Telegraph Avenue in Berkeley. He was lying in the gutter, literally, asking for spare change, but he still had a space bag of wine with him. I went up to him and I go, “Just keep looking up at the stars,” an Oscar Wilde reference, and we became best friends. He told me about growing up in Hong Kong and how he tried heroin when he eight. He used to be an underwater welder and had shark bites all over his torso. He was a total Neal Cassady.

It was Doug and his girlfriend. I don’t remember her name, so let’s just call her Sunshine, a white hippie girl who never put out. There were tons of those on Dead tour. Poor Doug.

In Portland, Doug was like, “I just met all these cool hobos under the bridge.” So we went under the bridge. They’re all gathered around this big guy. He’s got a giant brass bed right by the tracks, old school. He’s like, “I’m here because I keep oversleeping my train. I keep setting my alarm. I’m gonna catch this one.” We took LSD and then we gave LSD to all the hobos. There was a guy who didn’t speak English. They called him Frenchie. He must have been French Canadian. He sure talked like it. He goes, “It’s your birthday?” And he leaves. He comes back an hour later with an entire shopping cart full of Thunderbird wine. Every single person got their own bottle of Thunderbird wine.

They’re giving us advice, which is all conflicting, about getting on the train. But, finally, the train comes by and I just follow Doug, because Doug’s the man. We hop on the back engine and then the whole train stops. A railroad worker comes over to us and goes, “You can’t hop the engine. You can’t do that.” We’re like, “Oh, we’re sorry. What’s going on?” The guy explained, “Just follow these tracks about two or three miles and there’ll be empty box cars. There are a bunch of them. They’re going to take you back down to San Francisco.” By the way, lots of railroad workers totally think you’re cool, as long as you act cool.

We got off, in humility, and were walking down the tracks when the LSD really started kicking in. Thank God railroad tracks are easy to follow. You just stay in between the two rails. That’s fine. We just kept walking and we did find the boxcars. We ended up getting in there. Then some guy jumped on from some other place. We said, “No, you’re getting off.” Some random person trying to jump on your car that you don’t know, maybe that’s a bad idea.

We went down through Oregon. The train yard at Eugene is right next to town, so we get off the train and, all of a sudden, we got a ton of muffins from some weird Christians. Free muffins? Sure.

We were going to split it into two parties and hitchhike. I was going to hitchhike alone, but then we met this guy and he talked like this. I couldn’t understand why. I thought he might have got kicked in the head by a mule when he was young. He spoke in a monotone. I found out after talking to this guy for a while, he was a paint huffer growing up. Back where he grew up, that’s what all the kids did. So that would explain it. He said, “I don’t know where I’m going. The last people I traveled with ditched me here. Will you let me travel with you?” Of course, I went, “Ah, sure. Let’s do it. We’re just going to San Francisco. We’re going to a Grateful Dead concert, buddy.”

We ended up hopping together out of there. There were no open containers, so we’re on top of this giant thing full of lumber, in the indent at the end with some shorter beams. It was still my birthday and I was still tripping balls. The train was going and I just couldn’t help myself. I wanted to stand on top of that train and I wanted to train surf. I went up there, with my big old long, blonde hair, which was probably twice as thick as it is now. I stood on top, surfing that train.

And then they stopped the train. They said, “You can’t stand on top of the train. You all gotta get off.” They gave us bottles of water, which was very nice. They were kind of laughing about the whole thing when they threw us off about seven miles from the road to Santa Rosa. Me and that weird paint huffer had to walk all the way there. It didn’t take us long to hitchhike to San Francisco.

He was so happy when he got to Grateful Dead land. He’d never experienced such a thing like that before in his life, the poor little paint huffer from rural Oregon. I left him there. He said, “I don’t ever want to leave.” I always wonder what happened to him.

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