The Cotswold Way
First in a series about a trip that was both pure disaster and profoundly wonderful, in strange, unexpected ways that I still can't quite explain
I have discovered that not all travels are equally well-suited to the unplugged model.
“Discovered” as in: had my ass kicked. Today’s essay is the first in a series about a trip that, in most of the ways that count, was an utter disaster. Although I can’t take the blame for all of it–Mother Nature played a role here too–most of that disaster derived from equal parts of:
1. Not being able to look stuff up on my phone
2. My own stupidity
And yet, the trip was also profoundly wonderful in ways so strange and unlikely that I still have a hard time explaining them.
It started in Chipping Campden, which looks like the kind of place where the children in The Lion, The Witch and the Warlock might find Professor Kirke and his wardrobe: an English village of honey-colored stone and shops too expensive to be considered twee. So perhaps I should not have been surprised that, setting out from there on what was meant to be an 8-day, 102-mile-walk through the English countryside, quickly transformed into an excursion that made me feel as though I had stepped through a portal into an uncanny world of signs and portents.
I had first heard of the Cotswold Way a few years earlier, when I was housesitting in a town not far from its midway point. Now, with a birthday approaching, I thought a week or two of easy-ish hikes through rolling English countryside that ended each day with pints in a village pub and a room in a cozy inn would be the perfect way to celebrate. I also liked the idea of testing the unplugged concept in a new context; until then, I had only tried it in cities. I scheduled the trip for my birthday week and invited a dear friend to join me. We would start in Chipping Campden and end, some seven or eight or nine days later, depending on how much we dawdled, in Bath.
The plan began to go sideways even before it started. The friend who was supposed to accompany me had a last-minute family emergency that meant I would be doing the walk alone. And a delayed train from Birmingham meant I would get to the bus that would take me to the walk’s starting point just in time to see it pull away while, backpack bouncing, I ran futilely behind it like a humiliated turtle.


But no matter: eventually I arrived in Chipping Campden, took a walk down a main street full of people wearing the right kind of Wellingtons, and checked into an inn that looked ramshackle from the outside, but whose rooms were modern and spacious. After a short rest, I went downstairs for dinner in a pub so glowy and convivial that could have been the inspiration for the one in The Holiday. The hard-working waitress called me luv, and sat me in the corner, next to a family of 8 adults putting away a massive amount of food while talking about the even more massive amounts of frozen food—frozen chicken livers, to be exact— they would buy the next day.
Maybe it was the Jude Law/Cameron Diaz vibes or maybe it was a side effect of unexpectedly finding myself doing the walk alone. But as I made my way through my steak and Stilton pie, a rom/com fantasy took shape in my head that was so conventional it would have embarrassed Nancy Meyers. Maybe, I thought to myself, I would meet a handsome hiker along the trail, and maybe, over the course of the next several days, we would repeatedly cross paths, bumping into each other at overlooks and meeting up in pubs at the end of the day. Maybe he would be single and charming and smart. He would definitely be a great nature lover, because why else would he be walking the Cotswold Way. There would be mishaps and misunderstandings along the way, of course, but eventually, we would end up walking the trail together. Maybe it would be fate.
The next morning, I went down to breakfast at 7.30. There was only one person in the place: a fit, attractive man, older than me but still in range, with an air of sadness about him that made me think he was a widower. His pack was on the seat next to him.
I mean, honestly. What are the chances?
Bob was walking the Cotswold Way in a hard-driving 6 days, after having done a similar walk along Hadrian’s Way and finding it insufficiently grueling for his tastes. I got the impression that he disapproved of my more lackadaisical approach to the walk and that he thought it frankly bonkers that I didn’t have my accommodations booked ahead of time, but tension, as we all know, is at the heart of any good romantic comedy. Plus, I got points for carrying all my own gear, while he had organized his trip through one of those outfits that arranged his lodging and picked up and delivered his luggage each day–a fact that I think embarrassed him, until we exchanged the day’s destinations. He would be spending the night in Winchcombe, which was 18 miles away. I told him I would probably stay in Stanton, which was only ten.
“I’m starting slow,” I said, trying not to sound defensive.
“My wife always tells me to do that,” he replied.
Ah. So much for Jude Law.


I left Chipping Campden around 8.15, so enthusiastic to be off that I completely forgot to seek out the monument that marks the start of the Cotswold Way. (I did, however, come across a house that Graham Greene once lived in). It was gray and foggy, but the air was warm and I was soon sweating my way up the first hill. I checked my map––a pocket-sized booklet with the walk helpfully broken into stages–and realized I was headed up and quickly down Dover’s Hill–an annoying habit on the part of whoever designed the Cotswold Way to add roundabout and often difficult diversions in order to take in a view. In this case, the trail led across a road and then steeply to a view rendered nonexistent by the fog. Later, I would learn that the view was so expansively spectacular that the hill was still referred to as an amphitheater and that, in the 1600s, Mr Dover himself initiated some kind of English Olympic Games there that included fierce matches of shin-kicking. Apparently people came from miles away for this.
If I had known that at the time, maybe I would have liked the fog better. Instead, I just trudged back down to the same road I had crossed a few minutes earlier. According to my map, I was to go right, but here, the trailmarker pointed left. It made no sense, since the marker was clearly leading me back the way I had come. I walked a few meters along it, but everything in me was screaming that this was the wrong direction, so I turned around and went back to the turn-off point to see if I had missed something. I checked my map again, and confirmed that it was definitely pointing in the opposite direction. I circled the area to see if there wasn’t another arrow pointing in another direction. Finally, I decided to head in what intuitively felt like the right direction.
Which is how, less than 30 minutes into my 102-mile walk, I got lost. I walked about a half a mile down a steep decline before I realized the mistake and had to reverse course, walking back up what had magically turned into an even steeper incline.
Once I reached the actual trail and had stopped cursing myself, the next few miles were uneventful. I came across what I at first took to be some rare species of exotic English rodent that turned out, on closer inspection, to be an escaped guinea pig. A long, flat expanse along farmland opened magically, at one point, to a field carpeted in flowers. I passed enough 50-something men hiking alone to make me think that the Cotswold Way was some kind of IRL Bumble for the middle-aged.


A climb through open sheep pasture led to Broadway Tower, a wind-whipped folly designed in the 18th century by a landscaper with the excellent name of Capability Brown and augmented in the 20th, as was all the rage, with a nuclear bunker. From there, a long descent led to the pretty town of Broadway, bubbling with tourists browsing antique shops and eating ice cream. I stopped in a supposedly artisan bakery that served me a fridge-cold mini-pizza, and got instructions for regaining the trail from the sweet ladies in the tourist office who somehow turned the instructions to “go right, then left” into a 10-minute exegesis of Talmudic complexity.
It was a long, hot climb out of Broadway, and both the heat and the incline were intense enough for the next few miles, that I tossed aside the possibility–first entertained that morning over breakfast with Bob– of continuing any further that day than Stanton. It was early afternoon when I arrived, my boots coated in the thick mud that had made the final descent treacherously slippery. The town was acutely lovely, with the same gorgeous architecture as Broadway, and none of the touristy shops. Which is another way of saying there were no tourists. Which is another way of saying there were no places for tourists to stay. I kept looking for signs that might mark a hotel or bed and breakfast, but could find none. I paced the town looking for someone to ask, but only met two German guys who were also hiking. They were continuing on to Winchcombe, but they had read that there was a place to stay in one of the towns a mile or two up ahead.
“One or two, which was it?” I wanted to scream, because by now my feet were seriously hurting. But that seemed uncool, and in any case, the Germans had already walked on. Reluctantly, I followed suit.


Luckily, this part of the walk was lovely: grassy meadows dotted with ancient oak trees that glittered in the sunlight. Unluckily, the next town, Stanway, was even smaller than Stanton, with an ornate Jacobean manor house but, yet again no place to stay. I sat on the gates to the manor house and took off my boots, just to let my feet breathe while I studied my map despondently, willing it to suddenly display a charming little B&B or even a grim, cinderblock Travelodge. Needless to say, it failed me. There was nothing to do but continue to Wood Stanway, another mile on, and hope that that was the place the Germans had meant.
The sun disappeared, and the skies opened just as I crossed into a field marked with a warning that it contained a bull, which is not really the mental health boost one needs after 11 miles of hiking. Still, it spurred me to pick up the pace into Wood Stanley, which, it turned out, was not even a village, more a tiny collection of houses. I went from one door to the next, looking hopefully for an indication that it took lodgers, but found nothing, and frankly few signs of life. But as I stood there, miserably contemplating my options, a woman emerged from her home and began loading the trunk of her car. I asked if there was a B+B nearby, and it turned out there was one practically next door. I had passed it before, because it was unmarked. I went over to knock, no answer.
It was about this time that I realized that the Cotswold Way was perhaps not best suited to unplugged travel. Had I had my phone, I would have just looked up the B&B and called it. I would have looked up all the B+Bs that were almost certainly lurking in all those other towns I had passed through, and called them. Maybe, I would have even booked them online and they would have sent me instructions on how to find them. It had just not occurred to me that an establishment that depends on passing travelers for its business wouldn’t actually identify itself to those passing travelers. What do you mean, it’s your home?
I trudged back to the woman at her car, and she kindly offered to call her neighbor. But the neighbor didn’t answer, and I had no choice but to accept my fate. At least I knew the next place along the trail, Winchcombe, had actual accommodations since both Bob and the Germans had told me that was where they were staying the night. I must have looked dejected though, because the woman put down the crate of dog food she was carrying. “Do you want me to give you a ride?” she asked.
I paused. On the one hand, I was tired and sweaty and I had a feeling my toenails were starting to turn unseemly colors. On the other hand, accepting the ride would be cheating. On the other, other hand: cheating who? I wasn’t walking the Cotswold Way to prove anything; I was walking the Cotswold Way because I thought it would be fun.
I got in the car. As we drove, Debbie told me how she had moved to the Cotswolds from Cornwall 23 years earlier, and although she liked the area she missed the sea. It wasn’t her first time driving bedraggled hikers onward; she had a habit of picking them up and depositing them a little further down the line. I told her she was a kind person, and she didn’t demur. “Why wouldn’t you be?” she replied. “Kindness doesn’t cost anything.”
Debbie deposited me in front of the pub in Winchcombe where she and her husband liked to go for dinner. It had rooms, but they were fully booked. It also, however, had Bob, who seemed a bit peeved to see me. “How did you get here so fast?” he asked with an edge of suspicion or competition, I wasn’t sure which.
I confessed the truth, and we were friends again. I still had to find a place to stay though, so I headed back out. The two other inns in town turned out to be full as well, and I wasn’t stumbling across any obvious B&Bs. I had learned my lesson about them though, and this time stopped to ask the salesperson in a clothing shop if any existed. It took her a minute, but she recalled one about five-minutes’ walk away.
I had gone far enough up the street that I thought I must have passed it when I came to a red-haired woman talking to her neighbor on the sidewalk. “You must be looking for me,” she called out.
Sarah owned the B&B I was standing in front of, and ran the place with a no-nonsense moxie I immediately liked. She was disconcerted to learn that I didn’t have a reservation, but quickly set her mind to the task of finding me one. The ensuite room was booked by a gentleman. The other room was taken by a couple who were—and here she paused to whisper—religious. That left the Pink Room, but I’d have to share her bathroom.
I’ll take it, I said.


Sarah needed time to clean the room, so she sent me back to the pub. I seated myself at the bar and amused myself with their shelving system as I drained half a pint. Someone tapped me on the shoulder; it was Bob, holding a book out, his finger on the page. He asked me if I could speak French, then asked me to translate a line, though I had the distinct impression he could have done it himself: à chacun son goût.
We chatted some more. Often when I travel alone, I am protective of my solitude, eager to guard my own experience of a place and reluctant to be pulled into someone else’s. But that has changed on these unplugged trips, and I’ve marveled at how much more expansive I feel; more curious about other people’s experiences, more open to just seeing where things take me. Bob was gruff, a bit judgmental, and probably terrible dinner company. I invited him to join me anyway.
First though, I needed a shower and a rest. It was approaching the time when Sarah would let me in, so I agreed to meet Bob back at the pub in a couple of hours, and took a quick tour of Winchcombe. I liked the town. Less precious than Chipping Campden, and less touristy than Broadway, it felt like a real place, with dentists and hardware shops. I bought some superglue to repair a place where the rubber sole of my boot was gapping, and picked up some fruit and chocolate as reserves. There was a community center too, where a sign advertised a concert that evening by an ‘80s and ‘90s cover band called The Mashers. As I stood reading it, a man came out and unloaded a drum kit from his car. “I hear they’re very good,” he said with a wink.
Finally, I arrived back at Sarah’s. I opened the door, unlaced my muddy boats, and looked up to find her seated on the carpeted staircase, a kettle at her side while she talked to…Bob. When I had run into him at the pub, I had assumed—well-organized traveler on a booked tour that he was—that he was staying at the coveted inn. But no, he had just been hanging out until Sarah let him back in, like I was. He was the gentleman in the ensuite room.
Sarah was in the middle of a story about John, who lived a few towns over, ran his own B&B, and had a wife who rode horses and put on airs. There was clearly some rivalry between them, although to be fair, John–who apparently barked orders at his guests and took away their walking sticks because he considered them to be weapons—did sound like a tyrant. I invited Sarah to join Bob and me for dinner, but it was the season premiere of Strictly Come Dancing that night, and she wasn’t budging.
And so Bob and I went back to the pub, where the food was surprisingly good and the conversation surprisingly comfortable. We swapped stories of that day’s hike, and I tested my theory that ‘real’ trails with a purpose—old pilgrimage routes like the Camino, or ones that traversed a massive geological feature like the Appalachian trail—are better than ‘made up’ ones like the Cotswold Way, whose sole intention seemed to be meander around showing you some things. I’m not sure he bought it.
We were very different in other ways as well. There was an austerity to Bob–he liked to cook but didn’t eat much, and when I suggested we order a starter to share along with our mains, he rebuffed the idea in a way that made me think he found it wildly extravagant. We did bond over shared loves for reading and Warren Zevon, but mostly, we talked about his travels. Later, I would hear from Sarah and two other guests in her B&B that they found him arrogant, but to me Bob just seemed well-defended. He liked pushing himself at the gym, he liked going on onerous hikes, and he liked diving. It was something that he and his wife had done a lot of, before she died. That was seven years ago, but he still sometimes spoke of her in the present tense.
(That murmur you hear is the sound of my intuition saying ‘I told you so.’)
I asked him if he wanted to go see The Mashers with me. By now, the concert was well underway, the tables full, a few women dancing up front while the band played Heart of Glass. Bob bought me a drink. The beer was warm and flat, and although I noticed that the lead singer was the same man who had winked at me earlier, The Mashers, it must be said, were not very good. Still, it was fun to stand there in the back, watching a roomful of middle-aged people pretend, for as long as the music lasted, that they were still young.
We walked back to Sarah’s and said goodnight. I saw Bob the next morning at breakfast where, just like the day before, he had arrived well before anyone else. That day, he planned to walk 15 miles to Seven Springs, where the tour organizer had arranged for a car to pick him up and drive him to a hotel in Cheltenham where he would spend the night. We were soon joined at breakfast by the “religious” couple, who turned out to be an Episcopalian priest from the US named Jamie, and his wife Mary, just retired from teaching. Their itinerary was more leisurely, and they were scheduled to spend the night in Cleeve Hill, which was only 8 miles away.
The day before, when I had found Sarah chatting on the staircase with Bob, he had said that I should walk to Seven Springs too. I got the distinct impression that this was something the two of them had already discussed—an answer to the supposed problem of this kooky American woman traipsing around without a plan. I hadn’t responded then, and now, when he asked how far I was going, I said I still wasn’t sure. But I wondered if there wasn’t more to the question.
I sensed that what he was really asking was whether I wanted to walk with him. And while I would have been happy to meet up with him again for end-of-day pints somewhere down the line, I didn’t actually want to walk with him. I didn’t want to have to keep up with someone powering his way down the trail as quickly as possible. I didn’t want to lose the meditative quality of walking long distances in silence, and I definitely didn’t want to have to make conversation while I heaved myself up and down hills. More to the point, I didn’t want to be pinned down to a particular arrival destination. Rain was predicted all day—it had already started falling quite heavily—and I wanted the option, if I was soaked or tired or just not feeling it, to take a shorter day and spend the afternoon curled up somewhere, cozily reading a book.
But he hadn’t actually asked me if I wanted to walk together, so all I’d said in return was that I wasn’t sure how far I’d get that day. I got up from the table to finish packing, assuming we would say our goodbyes before we each left.
While I was still putting together my gear, a door opened downstairs, and I heard Bob saying goodbye to Sarah. I ran to the stairs to find him already in the doorway, his pack and raingear in place. “Bob,” I called down. “I hope we run into each other down the line.” I meant it: I would have loved to encounter him again in the pub in Birdlip or Painswick or any of the other curiously named towns that lay ahead. But he just mumbled a goodbye without turning around.
I realized then that, in my unwillingness to give a fixed answer on my day’s destination, I may have wounded him. Or maybe it hadn’t even gotten to that point, and he had walked out without saying goodbye in order to stave off even the possibility of rejection. In the moment of his departure, it definitely felt like Sarah’s door wasn’t the only thing he was closing. But I remembered something he had said over dinner the previous night. I had told him the story of Debbie, and what she had said about kindness as she drove me to Winchcombe. Bob had nodded thoughtfully. “There are a lot of different forms of kindness,” he said. “Sometimes, it just looks like talking to a lonely man in a pub.”
Maybe, that had been enough. At least for the first day.
The Addresses
Below, paid subscribers will find a list of the places where I ate, drank, and stayed along this first part of the Cotswold Way. But, a gentle reminder: wouldn’t it be more fun to find your own? (Paid subscribers also get access to The Unplugged Traveler’s chat).
Accommodations
The Lygon Arms: High Street, Chipping Campden. Not to be confused with the far more luxurious (as in Prince Harry was known to hang out there luxurious) hotel of the exact same name in Broadway, but still very nice. Spacious, stone-walled rooms with modern bathrooms and pretty textiles. I paid 145 pounds for bed and a very ample and delicious breakfast.
Blair House: 41 Gretton Rd, Winchcombe. A homey bed and breakfast in a graceful Georgian townhouse, overseen by the warm and wonderful Sarah, who is rightly proud of the breakfasts she serves, including scrambled organic eggs fresh from the neighbor’s chickens.
Restaurants, bars, cafés, etc
The Lygon Arms: High Street, Chipping Campden (again, not the Broadway one which, with its Michelin star, is probably good too). A popular dinner spot with locals, with solid versions of classic dishes, warm service, and a lively atmosphere, all of it served up in large portions
Otis and Belle Artisan Bakery, High Street, Broadway. The first place I came to on entering town from the Way, and a clear reminder that you should scope a town before just falling hungrily on the first place you see. The pide with nduja and olives I ordered was fridge cold, and when I asked for it to be heated was told, in this artisanal bakery, that they had no oven. They also had no toilet, which was my other reason for stopping. In my/their defense, I will say that their sourdough breads looked nice.
The White Hart Inn: High Street, Winchcombe. Accomplished pub food, including a properly crisp porchetta, a tasty roast chicken, and some of the best ‘chunky chips’ I’ve ever eaten.
Love this! Can’t wait to read more.
Loved this. Love even more that there's more to come!