FEW FORMS OF TRAVEL can be as frustrating, or as serendipitous, as hitching rides. This is particularly true in the sun-baked, windswept, thinly populated place that is Wyoming. Despite being the self-proclaimed Equality State, Wyoming has outlawed hitchhiking. I found this plenty ironic while waiting for hours alongside Highway 191 outside of Rock Springs on a simmering July afternoon in 2001. A state trooper had already run me off as I tried to catch traffic coming off I-80, so I had humped to the edge of town, hoping he wouldn't follow. I was en route from Denver to Jackson to do some camping, and I sat on my pack by the roadside, sticking my thumb out for every passing 18-wheeler and overloaded RV bound north toward Yellowstone. Nobody stopped. Men in cowboy hats glared as they flew by. The wind kicked the dust up and I was hit in the chest by a tumbleweed.

Finally a huge SUV skidded to a stop in the roadside gravel. I climbed in, profusely thanking the driver, a bearded, weathered man with gray hair. We rode through the parched landscape in silence until his cell phone rang:

Hitchhiking 101

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His daughter was in the parking lot at Denver's Red Rocks Amphitheatre for a Phil Lesh show, had forgotten her tickets, and wanted some strings pulled with "Uncle Bobby"—Weir, that is. Apparently this was no ordinary rancher. When he hung up, I asked him his name. "John Perry Barlow," he replied. Rancher, yes; as well as poet, essayist, political activist, lyricist for the Grateful Dead, and, in a strange twist, a campaign manager for Dick Cheney's 1978 congressional bid. (Today Barlow focuses his work on "cyberlibertarianism"—promoting individual liberty on the Internet.)

We drove a hundred miles to Pinedale, the conversation drifting between animal husbandry, Internet access in the developing world, and jam bands. I crashed at his house in a room with gold records adorning the walls. The next morning he told me he'd found me a lift to Jackson. We drove a couple miles and swung into a tiny municipal airstrip. A pilot friend had offered to pop us over in her single-engine Cessna. I was crammed in the back with Barlow's hundred-pound Samoyed as we lifted up over the barren landscape, the Tetons looming to the north. Barlow took the stick, navigating by the ribbon of highway two miles below us. His friend touched us down at Jackson airport, and we parked right next to Air Force Two. I still have a snapshot of myself, dirty with travel, grinning next to Dick Cheney's nose cone.