It was a sunny, mercifully dry day in August, and I asked a family friend, twenty-year-old Olivia Lew of Oak Bluffs (heading into her junior year at Middlebury College in Vermont), to accompany me. I thought the adventure required a sidekick, and across the gulf in our ages, we could appeal to drivers from seventeen to ninety-five.

We began our trip south of Circuit Avenue. That first experience of thrusting out our thumbs was as much a torment as the first day at a new school. Would anybody stop for us? Did we look okay? One thing we decided was that we needed a backstory. It wouldn’t do to let people know we were engaged in a journalistic lark; they might think their kindness was being taken advantage of. Besides, we wanted the experience to be as real and raw as it could be.

We waited seven minutes for our first ride – in hitchhiker time, an agony of rejection. Why was everyone passing us up? We were so wholesome, so cute! Olivia, like the girl from Ipanema, tall and thin and tan and lovely, had on an apricot-colored shift over a bathing suit. I wore a cotton blue and white paisley summer dress and a straw-boater hat. We realized almost immediately that if people are primed not to pick up riders – and apparently the majority of Americans are primed not to pick up riders – then Shirley Temple in tap shoes would not inspire them to stop. And then – yippee! – our first driver pulled over, a youngish guy in a battered Toyota Tacoma pickup truck.

“I’m only going as far as the hospital,” he said.

“We’ll take it!” we cried, clambering onto the passenger seat, where we squeezed in together. It was sort of in the direction we wanted to go.

Our benefactor lived in Vineyard Haven and worked at the hospital monitoring cardiograms. He told us he only picked up hitchhikers on-Island. Well, sure.

We said we would never attempt this anywhere else.

“When was the last time you hitched?” Olivia asked me as we waited for our next ride in the turnout west of the hospital.

I hated to break it to her, but it was back in 1969. I was traveling down from San Francisco with my boyfriend, and we stuck our thumbs out on the shoulder of Route 101 at the outskirts of San Jose. A Buick as big as, well, a Buick stopped for us. Two thuggish guys, each weighing an easy 280 pounds, glared over the dashboard. The man on the passenger side lumbered out of the car and gestured for my boyfriend to take the seat he’d been warming, whereupon it was understood that I was expected to sit in back with the fellow. How irregular was that?! Comparing notes later, my boyfriend and I both had the idea we’d be dead inside a quarter of an hour.

As we stood that distant day, petrified, at the side of the road, a cop car pulled up behind us. The standing thug yelped, “It’s The Man!,” piled back into the passenger seat, and the car peeled out in a cloud of outlaw dust. The cop motored us to the next off-ramp, all the while chiding us for hitching on the highway. He drove home the seriousness of the misdemeanor with a ticket for each of us: in this way, guardian angels can sometimes behave like nasty humans.

“So that’s why I haven’t hitched in the past thirty-six years,” I told Olivia.

“When was the last time you picked someone up?” she inquired.

“Nineteen-seventy. And that’s an even scarier story.”

But just then a vehicle slowed for us that looked like something from a poster for a movie rated R (for excessive violence). It was a demobilized Brink’s truck, gray, with medieval bolts protruding from all sides. The driver, a young man with a stubbled beard and wearing a Gilligan-style straw hat, peered out at us through the doorless aperture. I could tell Olivia was leery about climbing into the truck, so I hopped in first. I headed towards a ledge in the back, but Olivia very nearly lifted me off my feet to plunk me down closer to the driver. Turned out he was an apprentice in the plumbing trade, which you could have guessed from all the copper pipes and tools strewn about the truck. A mayo jar of murky-brown water sloshed around on his dashboard, but when asked what it was, he identified it as herbal tea. That was a relief. I had wondered whether he kept body parts pickled in it.

It took another four rides to deposit us at the Gay Head Cliffs in Aquinnah, one from a twentysomething guy in a Mini Cooper who was working as a nanny for a family in Lambert’s Cove; another from my pal Molly Finklestein, in her hydrangea-filled SUV; the third from an art professor from Castleton College in Vermont, traveling in a battered Dodge Caravan with his part-German shepherd Jono, groggy in the back seat. We had him drop us at the Chilmark Store because only days before Olivia had encountered a guy there so gorgeous, she was literally tongue-tied in his presence. Now that she’d had time to ratchet up her courage, she was ready to talk, should she see him again. Gorgeous Guy was nowhere to be found, however, so we hitched a ride in another Tacoma, this one driven by a young-lady-T-shirt designer from the East Village. She asked if we’d mind if she smoked, and who were we to refuse? Hitchhikers must be the most amenable breed of people in the world. She dropped us at the steps to the Cliffs.

Total travel time: One hour and twenty-five minutes.

One thing to keep in mind: If you hitch in one direction, you’re probably going to be hitching back in the other. After a bite to eat we headed down-Island again. State Road east from the Cliffs was so quiet, and the occasional passing driver so uninterested in two ride-seeking femmes, that we walked a good couple of miles. We began to wonder whether we had the stamina to stroll, if need be, all the way home, and the forced march gave new meaning to the second word in hitchhike.

Finally Olivia and I got a lift from a couple from Washington, DC, in an air-conditioned Lincoln Continental. Olivia had us dropped off at the Chilmark Store again, where she patrolled the porch and the interior for Gorgeous Guy, but he was elsewhere. A man in his forties, driving a Honda Pilot, took us the mile or so to the turnoff to Lucy Vincent Beach. He told us he and his wife, based in New York, had been renting in Chilmark for the past eleven years. I couldn’t resist the joke, “Isn’t it time to go home?”

Friends of Olivia’s, Crystal and Ryan, gave us a lift east on State Road and would have taken us all the way back to Oak Bluffs, but we thought we had to troll for fresh rides: we had them drop us at Alley’s General Store in West Tisbury.

There, four young guys in a van skidded to a stop. The two in back slid open the door and yanked down a seat for us to face them riding backwards. Just as I was forming the words, “Uh, I don’t think so,” Olivia hopped inside, and I reluctantly followed.

The guys turned out to be grad students at the American Film Institute in Los Angeles. We yakked about earthquakes, traffic, movies, with even a drop of metaphysics thrown in, because guys like that have the chops for it. When I learned the driver’s name was Charlie McDowell, I said, “Oh, your parents are movie stars!” (Malcolm McDowell from A Clockwork Orange and Mary Steenburgen, now married to Ted Danson.) The boys had to make a stop at the post office in Vineyard Haven, but they were willing to whiz us all the way back to Oak Bluffs. Cute as they were from Olivia’s point of view – I was the designated chaperone at this point – we declined. By now we were addicted to the changing panoply of drivers.

Two more rides got us home – another buddy of Olivia’s; a young Oak Bluffs woman in a Honda Accord, who apologized for her hanging catalytic converter (from the car, not her); and a couple of florists from Rhode Island in another Pilot, who let us out at the base of Circuit. Although Olivia lived a mere block away, we considered thumbing one last ride, because at this point we were hitching junkies.

Then Olivia remembered that I hadn’t told her the story of the last time I’d picked someone up: It was in the spring of 1970. I was heading north on Sepulveda Boulevard from UCLA. Although I’d sworn off hitching myself, I was still enough of a flower child to pick up riders wherever they presented themselves. That afternoon it was a short, spry guy in the usual layers of leather and bangles. He had scraggly, long, brown hair and beard. The minute he climbed in the car, he told me to hang a left onto Sunset and head for the beach: Government agents in a brown van were hot on his trail, and his life – and now mine – were in mortal danger. As he ranted, I realized I’d picked up some species of paranoid psychotic, and my brain went into overdrive trying to figure out a way to unload him. He pointed to a hilltop and ordered me to stop while he did reconnaissance from above.

“Stay here!” he barked before alighting from the car and scampering up the slope. I bore down on the accelerator and the car fishtailed back onto Sunset.
The following November news broke of the arrests of the killers of Sharon Tate and her friends. When photos of the suspects were flashed on TV screens across the nation, I recognized one of them: “Holy moly!” I cried, “I gave a ride to Charles Manson!”

I never picked up anyone again.

But as I scooped up my bike at Olivia’s, we made a date to hitch again to Aquinnah, same time next year. It’s easy, it’s fun, and your chances of running into Charles Manson are slim to nil.