Felicity Buckwinder | On the Road

There are so many ways a woman like Felicity Buckwinder aligns with Pilgrim’s virtues. One of the most prominent reasons being Cheryl’s relationship with the open road. Going through her journal entries in the ’70s reveals a young woman as obsessed with roadtrips and Mother Nature as we are. In a time when internet and cellphones were borderline nonexistent, Cheryl was traveling through the United States, Europe, and lesser traversed countries like Peru. She even found herself on the frontlines of a humanitarian crisis in Ethiopia; a place not many westerns traveled unless they were part of aid relief. Her courage and resourcefulness is the true embodiment of every Pilgrim we know and love.

Cheryl was a pioneer of her generation—blazing the trail for other women to rise as professional journalists—but her legacy doesn’t end there. She was a curator of stories; her life wildly cinematic. She was a staunch activist for women and children often using her platform to write about issues that mattered but may have been taboo at the time. Her assignments took her to far corners of the world, but she seemed to breeze from one location to the next as if it were as simple as breathing.

We are so honored Jessie was willing to bring her mother’s story home to Pilgrim. Both of these women embody a sense of adventure and interconnectedness in their travels we aspire to maintain in our own. We hope their adventures will encourage you to embrace your own wildness and independence on the road. In sharing their stories transparently, we hope you’ll tap into your own potential and find your way; just as Felicity Buckwinder found hers.

  • September 20, 1972

    In view of my life, I am not really surprised to find myself stranded about 35 miles in between Lovelock and Winnemucca, Nevada today.

    Susan and I have been here nearly 24 hours in a desolate rest area called Humboldt Canyon where the car inconveniently threw a rod yesterday. We are waiting for Norm to bring his truck to tow us back to Nevada City where I will attempt to rebuild the engine.

    We started out from Relief Hill yesterday morning on our way to Detroit and got about 250 miles when it happened. Norm got a ride going to SF, and Sweet Sue and I settled down to wait. After some time, we hitched to a bar about 5 miles down the road where we drowned our sorrows in beer and hot chocolate, respectively.

  • October 1, 1972

    I’ve learned the lesson of traveling this summer. It’s best to hang loose and do your miles alone unless you have a partner who is hanging loose and digging the same people. Russell is about the only person I know who could fill this position at this time. But that’s out, so it goes.

    Oh yes, I got propositioned by a dyke in a bar last night. She offered me $1,000 to spend the night with her. She hated Russell instantly and really got on his case and generally ignored Jan and Norm. I got a bit uptight when she started holding my hand and rubbing my thigh. I could not have dealt with her if I’d been alone.


    JM: Pictured left is Don Russell.

  • October 16, 1972 | Detroit

    The trip through Montana and South Dakota was depressing. I can’t imagine how people can live (and be happy) in such barren, desolate places, devoid of all vitality. I can’t imagine what it feels like to be young in those towns. I can’t imagine why anyone stays. Why does anyone stay in Detroit for that matter? Inertia is a pretty powerful force in the universe I guess.

    Cyndi and Molly both had shocks for me upon my return. Both are three months pregnant and having the kids as well as buying houses and settling down. I feel slightly deserted and betrayed by my “sisters in the struggle” because of these developments. Perhaps I have betrayed them too by constantly deserting them for my wandering. I suppose most women depend on a man for the stability in their lives rather than other women.

    I don’t have one person in particular that provides me with a stable base, but I do have my friends, Russell especially when I need something like that.


    JM: This entry is all too relatable. I find that my life on the road, though stable in its own right, separates me from my friends who have steady lives in Portland. Those in partnerships are making plans together to move, buy houses, and are forming regular habits. They have all been gracious to me when I am home and readily include me.

    Nonetheless, my vagabond ways keep me from being any kind of true dependable constant in their lives. I have my very own “Russell”—he is a friend I can always count on to be on my page. Perhaps because we are both single or because we have similar careers and lifestyles? I think at the end of the day we do gravitate for support and camaraderie to those whose interests and way of life are like our own.

  • November 15, 1972 | San Francisco

    The overall result of this week was to convince me—once again—that being alone allows a person so much more dignity and I’m anxious to leave for Europe soon. Alone I won’t have to deal with jealousy and anger because there will be no one to induce those emotions. Freedom from that is well worth the loneliness that will eventually afflict me at times. It is so much nobler to be lonely than to be torn apart and reduced to raw nerves in a relationship.


    JM: This short wild love affair with Philip ended tumultuously as the free love movement of the ’70s didn’t guarantee that people walked away unscathed. Mom ended up sleeping with her close friend, Tom. Philip slept with Jennifer while mom was in the room downstairs, only after they had spontaneously driven cross-country to rescue his dogs together. He attempted to sleep with some of mom’s friends while in her company. He became jealous and cold and that’s when mom decided the whole thing had taken a terrible turn. Once again she felt cheated and was ready to get on the road to bigger more important things.

  • December 1, 1972 | Big Apple

    What price does one have to pay to keep from going through all these things twice? I’m ready to bolt for the door and keep running until I’m across the ocean where I foolishly and blindly believe life will be simpler.

  • January 10, 1973 | Somewhere Over the Atlantic Ocean

    It is painful and difficult to relate the events of the last week but perhaps by writing of them here I can put it all behind me and start to view this step at last as an adventure and not as a drudge.

    It is astounding that only yesterday I was in Vermont and then in Kinderhook last night. Early this morning I caught the train to New York City and spent the day shopping for last-minute items, doing laundry, packing, banking, and sleeping before finally boarding this plane at 8:30 p.m. In a matter of hours, I will be in Luxenberg and eventually in Denmark.

    Russell is not with me nor will he be. We parted ways in Vermont and the shock and sadness have not yet worn off. We both feel that we’re doing the right thing and what we must do, but that is of little consolation at this time. I couldn’t promise to love him and be his lover and he couldn’t promise not to get strung out because of that. And so I’m alone once again and on my way to Europe, feeling not afraid or excited, just numb. And sick and exhausted due to strep throat contracted in Vermont and three hours of sleep last night.


    JM (03/07/17): By this time next week, I will also be flying over the Atlantic Ocean on my way to Denmark. A happy coincidence that I had discovered this entry only after booking my own flight over to Europe. I begin my five-week journey by visiting a childhood friend in Malmo for a few days. Then I hop over to Zurich to join up with a tour bus of folk musicians. 

    It’ll be a fast 3 weeks of breezing through many cities. I’ll have mom’s next journal with me—one where she describes her time living in London scrounging for work and reconciling her choice to be there in the first place. I conclude my Euro trip with a few days to spare in “The Big Smoke.” There I’ve arranged to meet up with “Sweet Sue,” as mom used to call her, where I intend to pick her brain and search for further insight into this beautiful puzzle.

  • January 26, 1973 | Helsinger, Denmark

    Going through living with pretenses of sanity and well-being can sometimes get one through the hard times but even perpetuating that simulacrum can become extremely painful. As Shirley so aptly observes, sometimes it’s just a matter of putting one foot in front of the other until you get through a difficult period.

    And so this week has found me visiting Hamlet’s Castle, The Louisiana Art Museum, hanging out at Kalories almost every evening with Jon and Kenan, and shopping in Copenhagen with Kenan, having dinner there and a lib evening with Kenan and Bettina (his friend). That’s one way of doing it.

    A cease-fire was announced this week as well as LBJ’s death, and both caught me by surprise. At this stage, I wouldn’t have thought that a declaration of peace could have a very profound effect on me, but as I read the paper, I had to hold back the tears. I still hesitate to believe it, but I am harboring the hope that it is true. The war has changed all of us so much, and the politics that sprang from the opposition to it changed my life so radically that its effects are irreversible.

    I will never trust the government or believe in authority again as I did until the age of 18. My lifestyle was formed by those politics, my aspirations and ambitions altered drastically, the friends I have, and my relationships with them were brought about by those politics and their accompanying ideas. If not for the war, I would have been more hesitant to embrace sexual freedom and women’s liberation. Once the new consciousness is attained, the eyes can never be closed in those directions again. I lost innocence, optimism, naïveté, trust, and faith in the radicalization process and gained cynicism, paranoia, and hate in the trade.

    Would I have been happier as the innocent? Married perhaps, a steady job? It’s hard to say. I don’t think my mind could have stayed closed to all the forces and ideas that did change me or that I could have escaped the traumas that formed (deformed?) me. It’s a moot point.

    The fact is that I am what I am. I now only have to discover the essence of that and then learn to live with it.


    Editor’s Note: Though this photo was taken in front of Notre Dame in Paris, I felt it was a beautiful representation of the era; especially a woman traveling through Europe in the ’70s.

  • February 16, 1973 | London

    Perhaps I have yet to define what a relationship should mean or be, what should be shared, and what should be kept. In each, it is different except for the mutual appreciation of the pleasures of the flesh. But with these pleasures inevitably comes pains, and, with the joys, the sorrows. Even if by some miracle of shuffling and the scale is even at the end, what was the point? Except to have experienced a little more of all of it. Perhaps they do not negate each other if that is what life (and love) is about.

    One cannot help but hope to cheat the scorekeeper or dodge the odds and somehow emerge with the balance in one’s favor, or at least unscathed by the wretchedness of it all. I suppose that it is that hope that lures me into the arena and bars me from the spectator stands. I seem to live a full, eventful life in comparison to most of my friends and acquaintances but still, it is not enough. Anger at myself for my own ingratitude still does not prevent its presence.


    JM (04/06/17): Today is my last day in London and this Euro/UK adventure. Turns out it’s hard to keep up with posting while on the road working. I had one day on tour to sort through a few entries and this particular one jumped out at me. I have carried Gregory Alan Isakov’s music with me through love and heartache. As we toured and I heard him play the songs that were my therapy during hardship they started to become my soundtrack to independence and self-discovery. I was reminded of the emotional ups and downs we’re all meant to endure. It was as relevant in 1973 as it is now in 2017. Forever trying to find the balance.

  • May 17, 1979 | Enroute from Hong Kong to Canton, China on a Train

    We got 30 minutes of shopping in yesterday so everyone hit the streets with a vengeance by 9:30 this morning. I bought a bigger camera bag and a calculator. Many bought watches and gold chains. Eva bought four calculators. I also bought a small purse. Everyone seems pleased with the bargains we’ve been finding. I sent 15 postcards to friends in the US, having stayed up past midnight to write them.

    This train, which we boarded at 1:30 in Hong Kong, is great. We are in “soft class,” a cut above the hard which only means the seats are farther apart. We have white lace curtains and doilies and Chinese paintings on the walls. Sometimes there is Chinese Muzak playing, which amuses me for some reason. The landscape has gone from hilly and sparsely populated to flat and sparsely populated. We’ve seen people riding water buffaloes or plowing with them, and others stooped over in rice patties with their coolie hats and Mao suits. The villages are picturesque, of course, but also seem to be in partial ruin. Nothing seems completely intact so far. Maybe it’s the advanced age or the dank planes that have wreaked such havoc…

    I’m about to brave the toilet situation, which is straddling a hole in the floor. We arrive in Canton in 45 minutes.

  • February 2, 1980 | New York City

    After a few hours of driving around the city looking for a toaster in secondhand stores, and getting the car washed, I’ve spent most of the day in bed because it’s so fucking cold in this apartment.

    . . . Last Saturday I was on the bus from Flagstaff to Phoenix with Willie’s band, smoking dope and drinking beer, and having a wonderful time. After the concert, we re-boarded the bus for an all night, 10-hour drive to Las Cruces, NM. Bee and Chris were passing the guitar back and forth, writing new tunes with B.C. humming or whistling along. We kept getting higher and higher on dope and beer. After I fell asleep I was awakened by Grady Martin trying to feel me up. After trying to ignore him I finally got up and moved. That was the only bad experience. I got along really well with Chris, Snake, B.C., Jody, and Bee.

  • Fall 1980 | Pampachiri Region of Peru

    JM: Mom on assignment for People Magazine.

    The Chicha Valley sites, stretching over an area of some 70 square miles, were far larger and more diverse than any in recent archeological history. Read the full story on People.com: “An American Woman Discovers An Ancient Empire Lost In The Mountains Of Peru.”

  • June 18, 1981 | Ayacucho, Peru

    This is the second and last night in this Turista Hotel and I’ll be glad to get to the quiet of Andahuaylas tomorrow after listening to this fucking blasting disco music from the bar across the courtyard. This version of civilization sucks.

  • June 19, 1981 | Andahuaylas, Peru

    In Peru, anyone wearing a beard is making a statement about his extreme leftist politics and Michael’s beard immediately qualifies him as a suspicious character. He looks like a “muy peligroso hombre” (very dangerous man) and is treated accordingly. Fortunately, I look like a harmless midget and help to neutralize his impact on the authorities.


    JM: Great español, madre. She used to joke she only knew how to say, “May I please have an ashtray?”

    Reading through her entries from Peru is incredible. All day and night drives in a Jeep she and the photographer, Michael, rented winding up what she describes as the most terrifying roads she’s ever encountered. Trucks and cars tipped over everywhere. Freezing cold climbing to high elevations and arriving in these towns to find that no hotels are available. Streets littered with officials toting machine guns. They removed their windshield wipers after parking and locked their cars with chains through the door handles.

  • June 19, 1981 | Andahuaylas, Peru

    Editor’s Note: I love photos like this of Cheryl. I often wonder what it would have been like to travel in the ’70s and ’80s—perhaps even the ’90s—when internet and mobile phones weren’t available and navigating countries such as Peru required courage and street intelligence.

  • June 19, 1981 | Andahuaylas, Peru

    Editor’s Note: This is another image that I love rooted in my passion for anthropology. The discovery in Peru was an archeological achievement we studied in one of my college courses. Knowing Cheryl was on the front lines writing about one of the few women working in the field of archaeology at the time adds another layer to Cheryl’s writing legacy. It’s been amazing to piece together different elements of her work to see just how far her achievements reached. 

  • July 1981

    Back in New York only a few days and I’m already itchin’ for the road—some story somewhere. It’s crazy after all my longing to be home.


    JM (5/01/2016): Not even a month I’ve been back in Portland after my trip overseas and I’m headed back out east. I love my bed and my creature comforts but there’s some kind of therapy the transience of the road provides that I crave time and time again.

  • August 11, 1981

    The next day we all went out on a 40-foot chartered fishing boat (I finally caught some rays) and Miles and Evans each caught a bluefish. Cicely was seasick and slept most of the time. Miles borrowed my running shorts and made a show of sniffing the crotch before putting them on. When he returned them to me later I imitated him sniffing and we both laughed.


    JM: A small excerpt from a long entry about mom’s days spent with Miles Davis for her article in People Magazine.

  • July 10, 1983 | Auburn, CA

    Last Sunday was Willie’s ‘picnic’ in New Jersey and Stolley and I spent the whole day—from noon to midnight—out there in the sweltering heat. We went in the limo with Connie and the kids and sat right on stage during Merle Haggard, Linda Ronstadt, Stray Cats, Waylon Jennings and, of course, Willie’s show. While they changed equipment, we were backstage on the bus and I got Merle’s autograph for David. Waylon, Emmylou Harris, and the Stray Cats also came on the bus and Stolley was in ecstasy. After the show, we went back to The Carlyle with them in the limo and they invited us up to have a room service dinner. I played chess with Willie (he won again) and Stolley talked to Connie and the kids. All in all, quite a day.

Written by

Hayli is a travel writer and photographer. Since adopting a nomadic lifestyle in 2013, she has traveled to 20 countries with a return to Southeast Asia planned for the end of 2018. From studying orangutans in Gunung Leuser National Park in Indonesia to riding a motorbike through Vietnam, Hayli is always looking for meaningful relationships on the road and ways to share her stories with her loved ones back home.

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