The Cleveland Way Group Trip Summary

It’s been a couple weeks since we returned from our fun-packed trip on the Cleveland Way. It was as exhausting as it was fun. Each day we made memories that I am sure each one of us will fondly recall for decades to come. Buckle in, there’s a lot of highlights!


Helsmley, seconds before starting

York: The House of Trembling Madness

Our flight to Heathrow was delayed just enough that we missed our train to York. We purchased new tickets for a later train and found ourselves with about an hour to kill. So we jumped in a cab and headed towards a pub that I’d discovered before my last walk. The Brie Louise, next to Euston Station, boasts an impossibly vast selection of real ale; we counted 22 casks. We each had a couple of outstanding pints and walked 2 minutes to Euston Tap to enjoy one more pint before our 2-hour ride up to York.

York was brimming over with well-heeled drunk revelers. Britain’s largest horse race had just wrapped up. As we stepped off the train, a throng of wobbly-legged, whimsical hat laden, equestrian enthusiasts staggered on. We dropped our stuff off and met up at The House of Trembling Madness, an aptly named second story medieval pub replete with the skulls of scores of dead things. Perhaps the most well-stocked beer retail store (on the first floor) I’ve ever seen in the UK, we spent the night drinking cans of British and continental NE IPAs and dry hopped sours. Halfway through the night, Bobby, my Australian walking buddy that I met on the Dales Way, joined us. Great reunion and a perfect preamble to the amble of the next dozen days.

As midnight approached, some of the group, exhausted from the trip, retired. Pete, Dennis T. and I headed out into the now quiet cobblestone streets of old York. York is an enchanting place. Its history runs as deep, if not deeper, than any other city in Britain. What makes York so amazing is that it has maintained more medieval architecture than any other British city. The zenith of this old worldness is concentrated on The Shambles, a medieval butcher’s street (coincidentally the street that inspired Diagon Alley). In that brisk midnight air, we sauntered alone down the incandescent lane, buildings slouching toward each other, pinching the visible night sky into a skinny river of stars.

We eventually ran into a couple who were very enthusiastic about the night’s second biggest sporting event. After the horse race, all anyone was talking about was the McGregor/Mayweather fight. The bars in York were reopening at 4am for fight fans. After the usual “oh you’re American!” conversations, they wanted to talk about the fight. Despite the couple having strong yet contradictory opinions about who would win, the husband, the best looking ice cream man I’ve ever seen, put £1,000 on McGregor. The next morning must have been rough for him.


York, midnight

Helmsley: The Night of the Broken Rib

The next morning, a few of us headed out and walked some of Wall Walk (a walk on top of the medieval rampart around the old city) and eventually met up with the rest of the crew, totaling 6 (me, Pete, the two Dennises, Jeremy and Bobby). Before we knew it, the streets of York were absolutely choked full of tourists.

Cleveland Way (2 of 16)

Getting Lost in Yorks Shadowy Places

It was with a bit of relief that we found ourself in a private hire van speeding away from the throngs of people towards Helmsley, the official start of the Cleveland Way. For 45 minutes, urbanity gave way to countryside as our driver instructed us on the subtle nuances regarding the various and numerous pejoratives for gypsies.

On the way into Helmsley, we spotted a tiny brewery, and that’s exactly where we headed after we dropped off our stuff. It was a fortuitous stop. Despite Helmsley Brewing’s slightly-larger-than-homebrewers’ set up, they brew some fantastic beer. The first noteworthy beer was a blonde dubbed “Striding the Riding” (“Riding” is an obsolete word that refers roughly to a Yorkshire county), the official beer of the Cleveland Way. Secondly was a stout named “Jacky Boy.” We sat in the uncomfortably warm Helmsley sun happily sipping pints of Jacky Boy, which we later decided, after encountering it at a few other stops along the trail, was the best beer of the trip. Turns out this was their first batch of the beer which they only released a week before we showed up.

We opted for a lackluster Indian dinner. Happily full and slightly lubricated, we set our sights on Helmsley’s two pubs. The first pub turned out to be way too high brow for a bunch of rowdy foreigners so we settled in at the Royal Oak where were we made friends with a funloving couple on a date weekend. We drank and laughed and sang. When the pub closed I wanted to wander. I love wandering villages at night. They are quiet and dark and mysterious. And while it often takes very little imagination to transport yourself back centuries in daylight in these country villages, at night, it takes absolutely none.

We stumbled into a Norman church graveyard, laid down and giggled and waxed drunkenly about the stars and times forgotten. It’s at this point we most certainly upset a ghost because an unexplainable force pulled Dennis T. from upright to ribcage-first over a tombstone. It must have hurt but Dennis played it off. We went back to hotel and we went to sleep. That ghost would haunt Dennis for the rest of the trip. He was in obvious pain every morning. We all worried and guessed at what that ghost did to him: torn cartilage, broken rib, bruised liver. By the end of the trip, not without some reason, Dennis posited that it was his rib AND liver giving him pain. Post-trip Xrays have determined it was a ghoulish and severe bruised rib.


Here Lies a Vengeful Ghost

Helmsley to Kilburn: Night of the Nine Pints

Our first day of walking was glorious. The terrain transitioned every half an hour. We toured the most romantic abbey ruins I’ve ever been to and reveled in the cool August air. We happily rolled into Kilburn, addressed our many minor pains and made our way to the only pub in the village: the Forrester Arms. A great meal was had.

Towards the end of the meal, the seventh of our merry band appeared. Jon had been in Buxton on business but couldn’t arrange to meet us in Helmsley. We retired to the patio, started smoking, and began with an odd ritual that has developed on all my previous walks.

It’s been my experience that the first night of a walk is always among the best, and this was no exception. As fate would have it, this modest three pull pub had beer from a tiny brewery I’ve only encountered one other time. On the Dales Way after an 18-mile day, I walked into a very isolated inn with one pull. They just opened the cask: an IPA from a Yorkshire brewery called Pennine Brewing. It was the best beer I’ve ever had on any of my walks. I had three pints in the course of 30 minutes and would have had more if I didn’t have another two miles to walk. It was so good that I unsuccessfully tried to get the brewery to send a pin of the beer to one of the pubs on the Cleveland Way. The beer at the Forrester Arms was not that IPA. It was a pleasant by-the-numbers golden ale. But it was perfect. Quaffable and moreish.

Here’s some math for you. A firkin is a cask with a volume of 10.8 gallons. That’s roughly 1,400 ounces. Due to the nature of casks, you can knock 10% of the total volume off for spillage and murky beer. So the effective volume of a cask is roughly 1,250 ounces. An imperial pint is 20 ounces. We calculate that six of us had nine pints each plus two for Bobby (he’s a wine guy). That’s 56 pints or 1,120 ounces. They opened that cask that day and it’s entirely conceivable that we were the only ones drinking out of it. We put a 90% dent in that firkin. So close, yet so far.

Dennis M. and I, the last standing, lolled on the patio talking to the locals after closing. I finished up a cigar to repeated and exasperated claims that “THAT’S QUITE A BLIFTER!” (in the most slangy English accent, pronounced “bliftah”), a phrase that I have repeated at least a hundred times since.

Kilburn to Osmotherly: Beautiful Walk, Low-Key Night

A beautiful walk that took us through the first dirty purple heather-clad moors, forests, fern-filled magical valleys, and bucolic hamlets. The approach to Osmotherly was particularly beautiful with the best-maintained trail I’ve ever walked, which lead us through backyard gardens, mysterious alleys, and dropped us quite suddenly in the town square. We enjoyed another decent meal but, perhaps mercifully, the beer was not great.

Jon and I walked around after everyone else retired. Drank a couple Auchentoshans in a nod to our British adventure last year and called it a night.

Osmotherly to Clay Bank Top: 404 Drone Not Found

This stage of the Cleveland Way overlaps with the Coast to Coast Walk. It was a strange experience to be on the same trail that I just walked in May. I’ve often wondered if I would be willing to rewalk a trail. Walking on the Coast to Coast again made me lean much further away from that possibility. Truthfully, this was one of the most stunning days on the walk but the surprise of newly discovered vistas was lost. Some of the magic was dulled. I knew what I was in for.

Cleveland Way (12 of 16)

Along with being a popular day hiking stretch, there’s a third long-distance trail that overlaps this section. As a result, the trail was more crowded than any other rural portion of the entire trail. We met a brother and sister from California spreading their father’s ashes along the Coast to Coast, which he walked 10 years prior. A wonderful tribute and testimony to meaning these walks imbue to those who embrace the challenge.

Cleveland Way (13 of 16)

Penning Dirty Limericks

Early on during the walk, Jeremy and Jon lagged behind. Jon brought a fancy drone to shoot video. The resulting video is stunning and there’s a palpable thrill watching the little machine whip through the sky. As the remaining five of us lounged at the Wainstones waiting for Jon and Jeremy we heard the unmistakable buzz of the drone zip above us and fly back to a peak about a mile away. At the top of the peak, we could barely make out the silhouettes of our two friends.

And we waited. And waited. Then the strangest scene began to unfold. We squinted at the ant-sized silhouettes. One of them was climbing down the steep hillside – a few degrees shy of a cliff face. We waited. The cliff figure was gone, presumably in the forest at the foot of the hill. The other figure started lumbering down the path (which was dangerously steep itself) at an excruciatingly slow pace. A few dozen paces. Sit down for a few minutes, repeat.


Wainstones Waiting

At this point, we had been waiting well north of an hour. We eventually made out that Jeremy was coming down the path carrying two packs, stopping every now and then hoping Jon would reappear. Jon was nowhere to be found. The drone had malfunctioned, dove in the forest, and Jon went after it.

The Wainstones was a 20-minute walk from the road where we were to be picked up for our accommodation. When Jeremy finally arrived, it was decided that I would go find Jon with his pack and the rest of the gang would go and relax at the inn.

I rigged Jon’s and my packs together and set off down to the forest, calling for Jon at regular intervals. After about half an hour I heard him call back, found him, and joined him in the forest for a fruitless hour-long drone recovery expedition. Jon was staying at another village, the driver for my inn was picking up his last guests for the night, and it was starting to get dark. I left Jon and headed for the pickup point jogging for half of it. Honestly, it was one of the best feelings of the walk, running on the path, pack on and sweating profusely after already hiking over a dozen miles. I have a tendency to view trail runners critically but I kind of get the rush.

I plopped down at the pub just as the boys were ordering. The Buck Inn, owned by an English/German couple specializes in German lagers. A few lagers later and life was back on track. Our food was German-inspired and locally sourced. The portions were enormous. Then we ate ice cream. We retired to the patio, convinced the owner to let us buy the unopened bottle of Monkey Shoulder, and drank and smoked. The bottle empty, we all remarked on all the beautiful things because, at that moment, life was perfect despite (or perhaps because of) the blisters, bruised rib, sore feet, aches, and pains.


Clay Bank Top to Great Ayton: Ukelele Amateur Hour

This day’s walk began in the purple desolation of the moors. It was an endless sea of dull purple from the flowering heather, which only flowers for a month each year. The path was wide and easy. Right around 1pm, we exited down and out of the moors into a little hamlet where we ate a packed lunch on the side of a country road and chuckled at Bobby as he made friends with a curious and hungry horse.

It started to rain just as we entered another forest. We picked handfuls of wild blackberries, every other berry just ripe enough to be more sweet than tart. A few of the party straggled behind so those of us up front sat down under a large tree and listened as the heaviest rain of the whole trip fell. The sound was soothing. Wild berries, rain on leaves, great company in no hurry – bliss.

When the group was whole and the rain let up, we made our way a quarter mile up to a particularly prominent Captian Cook monument, and one our Australian was thrilled to visit. We called our innkeepers, and they came to pick us up in two comically small vehicles.

This was the low point of the trip. Everyone seemed to have some sort ailment. Pete was fighting a nasty flu/cold and his feet hurt, Jeremy’s boots were causing him serious grief, a ghost was constantly stabbing Dennis T, Bobby, nearly a septuagenarian, was starting to feel all the miles, and Jon was crestfallen over the loss of his drone and fighting a fierce case of plantar fasciitis. Dennis M. was holding up but that was to be short-lived. There was talk of some people bailing out for the next leg.

Despite all the physical issues, spirits were high. We had a wonderful meal and settled into our inn for the night. We were delighted to see what looked like a folk band coming in for a good old-fashioned foot-stomping country jamboree. Our enthusiasm slowly dissolved into disappointment when we realized the gathering consisted of nearly a dozen ukelele beginners playing American songs – over and over. Ugh.

Despite the setback, those of us not sick or exhausted made do. We convinced the bartender to let us coach him through making us a round of something resembling old fashioneds. It was truly a cultural experience. By the end of the night, Dennis M., Jon, and I were sipping out of outlandish goblets full of berries and gin, making friends in perhaps the drunkest pub I’ve ever been in. We sipped as the pub closed (this was becoming a habit) and headed to bed.

Great Ayton to Saltburn: The Night of Questionable Decisions

We woke up that Friday morning ready for the day. Every single person was going to hike, no matter how bad they hurt. True grit.


Early in the day, I fell behind with Bobby and we talked about life and his art. Dennis T.’s hip flexor went haywire. He told us to go ahead and he would go at his own pace. At lunchtime, we reassembled at a strategically placed pub on the trail. Dennis M. rolled in with his hand taped up. He slipped in some mud and sliced his palm open. While he was cleaning his wound, Dennis T. hobbled in and called a cab for the day’s last five miles. The rest of us set off for Saltburn, eager to see the coast and say goodbye to the moors.


The Stretching of the Dennis

Right before we walked into Saltburn we crossed under an impossibly tall Victorian red brick viaduct.


Saltburn is a cool place. A Victorian city with a grand train station, beautiful main street, an old-school funicular, and a bunch of seaside restaurants. Jon and I bought whimsical hats on the way in.


The Poo PSA is Out of Control

One interesting nugget the people in Great Ayton told us was that the women of Saltburn could be characterized by a marked lack of moral virtue. Of course, this information was bundled in colorful English slang. Whether the good people of Great Ayton’s assessment of Saltburn was true, we never found out. But we did manage to have a fantastic night in Saltburn, regardless of the moral fiber of the ladyfolk.

Saltburn was the biggest town on the path thus far, so we’re hoping for some Friday night live music. We were in luck. One of the seaside pubs was hosting a band called the Beer Dogs. Perfect. The band was great and by the end of the night, almost everyone in our party had been on the dance floor.

As the pub closed, Jon and I wanted to find another spot to party. We ask a number of people where to go. A single theme emerged: Redcar. The problem was that half the people said Redcar was where the party was and the other half adamantly advised we not go there. We got the distinct impression it was not a nice place. So we asked a cab driver who was waiting for her rider. She said it was fine and she could get us there in half the time that anyone else could.

We started to head aimlessly down the quiet streets of Saltburn when that same cab came flying around the corner: “I’ll take you to Redcar. Get in.” Jon and I shrugged at each other and jumped in only to discover that there was another rider: A 20 something woman that lived in Redcar. I got the impression we were the cab driver’s way of giving the local a free ride home.

Not knowing where we wanted to go other than the name of the town, we solicited the woman’s advice. She suggested someplace and said that she could take us. Score, a local guide.

We rolled up to a modern bar with a DJ and dance floor and a ton of craft beer and liquor. Total score. Jon and I, bedecked in hats could have had two heads for all the staring we received. It became apparent that Americans were a bit of novelty in Redcar. Our guide suggested we get some shots of tequila, so we got a round and sat down to watch the gyrating Redcar locals do Friday night. Jon and I downed our shots (which I should note are half the volume of American shots). Our guide took a sip and her face went all twisty. “Have you ever had tequila before?” Her “No.” I guess she suggested it thinking that’s what we do in Arizona. A sentiment that was somehow echoed in the drunken “There’s a sneck en my boot!!” yelled repeatedly at us in an incongruous southern accent from our booth neighbor.


Making Friends With Redcar Drunks

The night ended in a shrug and a 3am McDonalds drive-through visit. Here’s something you may never have considered: speeding home in the back of cab at 3am after drinking too much is not made any more enjoyable by roundabouts.

The next day, by far the longest day of the walk, was not made any more enjoyable by our late night shenanigans.

Saltburn to Robin Hood’s Bay: The Long And Winding Road

Saturday was a day shrouded in uncertainty. We wanted to walk to Whitby, which by itself would have been a very long walk, but because it was a weekend and Whitby is a popular vacation spot, all the accommodations required a two-night stay. Our solution was to book two nights in the next destination (Robin Hood’s Bay), reasoning that we could walk to Whitby and bus or taxi down to Robin Hood’s Bay and bus or taxi back up the next morning and hike the trail back to Robin Hood’s Bay. It was a clumsy solution and one that became impractical for everyone.

Bobby was already booked into a different village entirely. No one, myself included was willing to commit to the 28-miles of the undulated coastal path in a single day. For my part, I wanted to do as much as I could, at least try for Whitby: about 20 miles. But I was operating on too little sleep and had partied a little too hard the night before to make any solid commitments. Feeling a little antisocial, I pulled out from the group, breaking into the stride I usually walk. It took about 10 minutes. I was happy and energized.


I chewed up the miles. I flew. I was undeterred. At mile 9, I rushed into enchanting Staithes, picked up two meat pies and some juice. The butcher laughed at me for thinking I was going to make it to Robin Hood’s Bay before nightfall. The rest of party stopped for lunch in Saithes resulting in only Jeremy and Jon continuing the day’s walk.



I don’t drink red bull. Like seriously, I don’t think I’ve ever had one. I drank two. Holy shit, I flew. I ascended hills like they were nothing. I felt superhuman. I logged my fastest walking mile ever: just shy of 14:49 minutes (no jogging). Other than the drinks and pies, I only stopped briefly to buy an ice cream cone from an ice cream truck parked on the path.



It was a beautiful path. The path drove straight up to a plateau for a couple miles and then plunged down into a hidden coastal village, scenery fit for adventure novels. Hidden beaches, caves, waterfalls. It had everything. But I wasn’t stopping for anything. I was going to try for Robin Hood’s Bay.

Luckily, I’d been to Whitby before so I knew where to go. I had to fight the urge to push the ambling holidaymakers out of my way, I was so single-minded.


At mile 26 the gas in the tank began to go. I walked this small portion on the Coast to Coast – in fact, it was the last three miles of the Coast to Coast. I remembered the frustration of knowing that Robin Hood’s Bay was so close but yet unseen.

At almost exactly nine hours (6pm) after I left Saltburn, I arrived in familiar Robin Hood’s Bay, phone at 1%. I was tired but after a shower and some facetime with the fam, I was ready to eat. The Dennises, Pete, and I had a wonderful meal outside while we waited to hear from Jon and Jeremy. Jeremy stubbled in around 8:15pm, went to his room and passed out.


Dinner in Robin Hood’s Bay

The remaining 4 of us made our way down into the old part of Robin Hood’s Bay and discovered 3 bars I managed to miss on my previous two night stay there. The night ended when Jon showed up at 10:30 (having spent some time in Whitby), much too late to check into his B&B. Luckily (or unluckily as it turned out) it was the same place I stayed at in May so I hoped I could smooth things over with his host by being a familiar face. Not so much. I don’t recall ever being so thoroughly dressed down by anyone. His host was PISSED – and not entirely unreasonably. After a tense tongue lashing, he let Jon in. In the morning the two made up and everything was rainbows.


Jeremy’s app calculated 28 miles, mine 29 and Jon’s 27.5. We’ll call it 28 miles.

Day of Rest: I Hate Fish and Chips

Sunday was a much-needed respite day. We took the bus up to Whitby. Jon and I stopped into the first legitimate cocktail bar on the trail and had some late morning Singapore Slings then met up with everyone else (sans Bobby) at Whitby Brewing, right in the shadow of Whitby Abbey.

After a couple of failed attempts for lunch (Whitby was an absolute zoo), we settled on some nondescript fish and chip shop. I was hoping they had a fish sandwich, a Whitby favorite, but we were all stuck with fish and chips. I really don’t know who likes this stuff. It’s greasy even when it’s “not greasy” and bland. No amount of vinegar can fix that problem. Blech. Can’t stand it. I vow to never eat it again.

After lunch, we hit up a “micropub” I’d read about but missed on my last visit. We each had a well-served pint and chat with the affable owner. He gave us a few tips about Scarborough, the next town on the trail.


Whitby Crew

After a beer, we were all feeling a bit sluggish so we boarded the bus back to Robin Hood’s Bay. The remainder of the day and night consisted of meeting back up with Bobby, pub hopping, a solid meal, and an embarrassing showing in the local quiz night. After the pub closed, Jon and I entertained a young woman and the pub bartender on the patio of our BnB.


Robin Hood’s Bay, Album Dropping Next Year

I hauled some sour beers from York and I was happy to share with two very strange people. The girl who, despite being in England for two weeks, had developed a distinct English accent, was the poster child for millennials. Full of opinions, lacking any factual basis for said opinions and oozing victimhood despite clearly coming from a very privileged background. She was on her way to “work with the land” on her family’s Scottish estate for 6 months. The bartender was a misanthrope who defined his world by naming the things he didn’t like. It was a weird hour.

Despite this minor hiccup, Robin Hood’s Bay charmed us. It’s a place that defies accurate description. I’ve stayed there a total of 4 nights now, making it my most visited place in England after London. It’s full of secrets and ghosts. An old smuggling port, the winding dark alleys, the bulwark seafront, the old weathered shops- it’s enchanting. I’d love to go back.

Robin Hood’s Bay to Scarborough: Parsley, Rosemary and Surprise Cantillion

The walk to Scarborough was a pleasantly uneventful stroll along the coastline. Jon, Jeremy, and I pulled ahead of the group. When we reached the outskirts of Scarborough we stopped for some delicious ice cream and sauntered to our hotel. Scarborough is not currently a nice place. At one time the town was a bustling vacation hub, the very center of sophistication of the Yorkshire coast. The sad town has all the infrastructure of a once prominent destination but now feels like a rustbelt town. Like Pittsburg meets San Francisco.


We met up with Jon’s Buxton buddy Jamie at a little beer bar, had a beer or two, and hunted down some dinner. I think we must have been particularly loud that night because we caught a few servers snickering at us. It could have also been that we ate a staggering amount of food.


Dennis T. had read in an old beer guide that there was a pub that specialized in Belgian beers. Tired of English beer, we happily trudged to the pub. “We read you have Cantillon. Is that true?” Bartender: blank stare. “Let me ask.” The affable lady publican enters. “Ya’ll got any of that Cantillion.” Publican: “Oh no. We stopped trying that. No one here ever bought the Cant-a-Lon. Sorry.” Bummer. Publican: “Let me check downstairs and see if there’s anything laying around.”

A few minutes pass…

The Publican enters with her arms full of Cantillion and Gueze Boon. Publican: “I found these but I’m afraid they’re all dusty so I can’t sell them to you.” Blank stares. “So, just put some money in the charity jar over there.” Us: “Wait. What?” Publican: “These are out of code. I can’t sell them. Just leave a donation.” Disbelief.

Sit down, check date codes, roughly 5-8 years old. Where the hell are we? What is this magical bizarro world? Commence drinking.

20 glorious minutes later, enters Publican with another armful of sours: “These are out of code too. Just leave a donation. I can’t sell these here. People just complain about them.” More drinking, more disbelief.

We left the pub in a state of stupid wonder. We wanted to check out another pub we had heard about but it was closed, so the group broke in two. Jeremy, Jon, Jamie (jinglehymershcmit) and I headed heedless into the heart of the town while the rest of group went back to a pub we passed a few blocks back.



Triple J and I found something resembling a cocktail bar. It had respectable cocktails on the menu but the execution was terrible. Cloyingly sweet and undrinkable. We hit a couple more unremarkable pubs and turned in for the night to charge for our last day of walking.

Scarborough to Filey: Sometimes, You Make the Fun

Our last day of walking was our shortest day. The forecast promised rain but delivered relatively dry dramatic and overcast skies. We walked slowly along the coast, only stopping for an occasional picture. As we reached the marker for the end of the walk, I think we were all glad to be done.

Cleveland Way (16 of 16)


Everyone worked hard to finish. Not a single person didn’t have to overcome some ailment but by the end, everyone had worked past the pain and made it to the finish. It’s cliche but true: it’s not the pain that we’ll remember from this trip. It’ll be the mosaic of memories we intentionally forged by getting out there and doing something different and challenging.


That night was fantastic. It was our last night with Bobby, a man our entire group grew to love and admire. We had a lovely tapas dinner, administered by the wonderfully attentive Spanish owner of the restaurant. It was a blur of amazing small dishes, banter, and wine. Later, we came within one tiny point of tying for first in the local pub quiz. We made friends everywhere.

As the end of the night drew near, we knew we had one last hurrah left in us. But where to go? There was only one answer. Every single person told us, “this pub is great, that restaurant is good,” but unanimously and forcefully warned us not to go to the Three Tuns. It had to be the Three Tuns. In minutes we found ourselves in a divey pub with terrible beer, glaring natives, a digital jukebox, and a small pool table. It was loud and it was not clean. I think one of us saw a drug deal go down.

But with 5 songs for a pound and hours to kill, we made it our bar for the night, to the chagrin of a miserable looking lot in the corner (although a couple of the locals warmed up to us and joined in on the party). We drank shitty tequila, yelled out lyrics to shitty music, and sent Bobby off with a bang. It was a perfect ending to a great walk. Last call, we staggered to our wonderful BnB and slept the sleep of the satisfied.

Newcastle: Delightful Surprise

In the morning, Bobby left for the states, Jon and Jamie headed to Manchester and the rest of us got on a train headed to Newcastle. Why Newcastle? I have no idea. We looked at a map and saw a familiar name. Newcastle is situated in such a way that you’d never accidentally end up there. It’s not on the way to anything, the last outpost of North East England with a old crumbled wall to keep the barbarians out.

Cleveland Way (1 of 16)

We had absolutely no expectation. As we stepped out of the train we were confronted with beautiful architecture and a city full of bars and restaurants. It turns out Newcastle is a bit of a college town, playing host to two large universities.

After we dropped out stuff at the hotel, we discovered a brand new shiny hip craft beer bar on the ground floor of our hotel building. And then next door to the beer bar was another craft beer bar. We were gobstruck.

Someone in the group found us a promising BBQ joint to hit for lunch. As we walked to the restaurant, the scale and beauty of Newcastle really struck me. It’s a very vertical city where the streets seamlessly incorporated medieval, Georgian, Victorian, and modern architecture. The restaurant was in some sort of medieval building with long winding corridors and tiny rooms. The men’s restroom had an old school fireplace in it.


After a power nap, we hit the city excited to see the nightlife. Turns out though, that school was not yet in session so the city was subdued. We had a few beers, ate at a Greek place and had a few more beers. At this point, the trip caught up to me. I was exhausted beyond measure and called it a night.

I’d love to see Newcastle again.

Darlington: Quiet Bliss

In the morning, we took a short 30-minute train ride down to a charming little market town called Darlington. There’s really nothing to see in Darlington. It was simply the closest train station to the CAMRA national pub of the year, George & Dragon, in tiny Hudswell, 15 miles away.

Nevertheless, we gave Darlington a lazy walk. It’s a charming little place. As we sipped on some coffee, I noticed that the restaurant next door was advertising Mexican food. We browsed the menu and decided some apps didn’t sound half bad.


I am still confused about what we walked into. The menu was half Mexican and half Cajun, really playing on some cartoon morbid connection between voodoo and dias de los muertos. But what really threw me was the bar. It had a huge selection of spirits. More bourbon than I’d seen in any British bar. Cocktails? Yes! A true blue, oddly themed cocktail joint.

Before the bouncy bartender handed us the cocktail menu I asked if they could make a Paloma. “Of course.” It was fantastic. A round of cocktails, and maybe a second round for me, and I was right as rain. We walked around the town a little more. Visited a pub or two and went for a nap.

Our cab arrived at 4:30. He drove us to the George & Dragon. We walked into an empty pub, the publican stabbing and stocking the first fire in months (it was a coal fire even). I’d been the George & Dragon before, twice in fact. In May, I learned the CAMRA national pub of the year was a few miles off the Coast to Coast trail, so I plotted a poorly planned path to the pub (say that five times fast). I had such a great time that I spent the following day, my rest day, there as well.


After we’d had a pint, I ran into the publican on the way to the bathroom. “You were here from the Coast to Coast weren’t you?” “Yes. Cool! you remembered me.” It’s the little things in life.

The publican promised there was a brown ale next in line if we blew a cask. So a thunderous applause broke out when the copublican (the previously mentioned publican’s wife) blew one of the beers. It was brown the rest of the night. Fresh, delicious brown, on a cool, drizzly Yorkshire night.


It was a quiet night. At one point while talking to the husband publican: “Your son’s in a wheelchair right?” I don’t remember having this conversation. I must have been extremely comfortable during my last visit. We had a great talk. Such a warm and intelligent couple. We ate and soaked in the peace and analog pleasure of spinning records.

Dennis M. joined me in the cold drizzle while I smoked an hour-long cigar. We talked about some very deep things. Parts of me I don’t share with anyone.  At some point, the publican joined us and taught us about a historic pub game they still play there. It was a special night.


On my way back into the pub, I got pulled into a conversation with two local women. They were extremely nice but man, did they like to argue. With me, with each other, with anyone listening. It was kind of fun.

Our taxi arrived four (or was it five) hours after we arrived and shuttled us back to Darlington. It was 10:30ish, so I wasn’t ready to call it a night. I have a tradition that I like to find an old-fashioned after I finish a walk. I resolved to head by to the voodoo Mexican cocktail place. Dennis M. and Jeremy joined me. We drank our drinks and headed back to the hotel.

But I wasn’t done. Sensing Jeremy and Dennis were too tired for more, I unexpectedly ran out of the elevator and out down the street. Everything was closing at this point, so I asked some locals and they pointed me to a colorful pub up the street.

A local guy, enamored that I was American, proceeded to pepper me with a million questions. That was also kind of fun. As that pub closed, I called it and headed back to the hotel.

London: End of Trip Blues

After a two and half hour train ride back to King’s Cross station, we found ourselves right back where we started the trip. One day left, we dumped our stuff in the hotel, and Pete took off to check out Shoreditch. The Dennises, Jeremy, and I headed the British Museum for a quick jaunt around the exhibits. We then walked around London, hitting a prominent pub before settling on a blues bar that Dennis T. had previously visited. After a good time, we went back to the hotel. I met up with Jon and couple other familiar faces for a couple final cocktails in England. Woke up, got on plane and immediately fell asleep.


Conclusion: A Different Kind of Joy

Truth be told, I was apprehensive to take anyone on one of my walks. I really enjoy the solitude that these walks bring. There was only one day where I felt close to the kind of wholeness that I get on my solo walks but the trade-off was that I was never lonely and I had a ton of fun. My fondest memories of my solo walks occur someplace isolated where I can fold into myself. My fondest memories of this trip will likely be all of us huddled around a dimly lit pub table laughing hysterically. We were loud and happy and ourselves. At its best, we were unrestrained, living life to the absolute fullest. I regard it as a total success.

I crossed my 500th-mile hiking in England on the last day of the walk (cue The Proclaimers) and I am still just as enchanted as my first few miles. I expect I will be satiated for a few months, but come Spring, I know the itch will return. Then, perhaps I will walk 500 hundred more. Until then…