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The Legend of Barefoot Brad

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Start – Stop: Brattleboro, Vt – Hoosac Tunnel, Ma

Distance: 39.8 mi

Elevation Gain: 4138 ft

Riding Time: 5:00

Time Awake Spent in Pursuit of The Trip, Roughly: 8:00

Weather: When we started it was sunny but cool, and then the wind picked up, and then it rained for a while and the wind didn’t stop. In fact the wind didn’t stop at all while we were in Vermont.

Day 01 Objectives & Points of Interest

  1. Enjoy a morning coffee before riding out of town.
  2. Avoid attracting a haunting.
  3. Lay eyes on some of Vermont’s wonderful New England architecture.
  4. At all cost avoid contracting Lyme’s Disease.
  5. Walk inside the haunted Hoosac tunnel and survive.

Vermont. So green. So artisanal. So Vermont. This would be my first time doing any riding of note on the East Coast. Having talked to friends about the area, I was expecting a flogging. Though ancient and relatively low in altitude, the mountains of Vermont are supposedly steep and generous, incessantly jabbing you like a flyweight, unlike the haymakers thrown by Western heavyweights. This land is not flat and we expected to be going up and down constantly, resulting in an elevation profile akin to the EKG of a high strung athlete.

Fortunately our experience on the first day was much gentler than this. It could have been that our route took us into Massachusetts, or that Benedict—with an eye for the pastoral and experiential—guided us around the more arduous climbs. I can’t say, I don’t know the area. What I do know is that it only takes a few minutes of riding through this countryside to understand where the artisanal influence comes from. Like a watershed that feeds a river, this region is saturated in the artisanal, and the gravity of culture focuses this artisanal abundance in the farms, hamlets, towns, and cities of Vermont.

“I could make a failed attempt at a W.G. Sebald-esque description of the region but we have all these wonderful photos that will save me the shame and you the disgust of reading such a travesty, so scroll down when you want to go on a virtual artisan safari.”

Today’s stated destination was the Hoosac Tunnel, a known and mapped location on this Earth. But our real search was for the lost hamlet of Zoar. According to legend, Zoar exists in the green hills of southwestern Vermont. Believers hold that it is an artisanal Shangri-La, where the finest yogurts gurgle up through the earth and form fantastic pools throughout the township. The yogurt is always fresh, clean and ready to slurp. In Zoar everyone wears hand-tooled sandals and intricately-woven ponchos. Avocados grow year-round and high-grade coffee, coconut water, and juiced wheat grass pours from the town’s many fountains. The denizens read Hawthorne, Poe, and Melville aloud in the town’s square and it is maple syrup that that binds the whole works together.

The problem is no one knows what the entrance to Zoar looks like. Is it a tombstone, a dead end road, a P.O. Box in some random post office squat? We kept our eyes open (to no avail) for drops of yogurt and streaks of syrup because legend holds that those who know of Zoar and travel freely to and from that land leave a slight trace of these exquisite substances in their wake. So keep your eyes open fellow travelers, and if luck is on your side you might find yourself bathing in the mystical yogurt pools of Zoar.


There was no rush to start. Of course we were excited to ride but there was a real fear of setting a precedent of early to rise, early to ride. Daniel in particular was terrified of establishing an early start time. So today was casual, what we’re calling a "comfortable departure." Sarah and Mary played checkers in the foyer of the motel and the rest of us calmly squirreled Clif Bars and snacks into the various stash spots around our bikes. This was easy, this was fluid, we accepted this additional time as a gift. #blessed
Påtz tucking a little away for later.
Maddwikkedtouah Starter Pack #2.
Bryan is happy to oblige. He'd be tearing our legs off in no time.
The tour has officially begun.
The mighty Connecticut River. To your left is New Hampshire, to your right is Vermont. This is as close as we'll ever get to NH. Sorry.
Where there are rivers there are bridges.
We’re already breaking the law by creeping through a closed, off-road construction site. But that’s who we are, born rebels and heretics. Paladins of the counterculture. You can’t block the road. We OWN the road!!!
Covered Bridge! And we haven’t even left town. We hit our first covered bridge on the way out of Brattleboro and it is glorious.
"My cute feet!" Benedict auditions his new shoes—an artisan is as an artisan does.

The Greenriver Bridge

A covered bridge so nice we road through it twice and then made our way into the countryside.
The roads, especially the gravel ones, are SO impressive. How they exist without a hint of washboard is beyond me. Are there road gnomes? Do they have unique Vermont-only grading machines? These roads weren’t what I was expecting. Even more so when you consider that mud season has only just passed. From what I understand, mud season is distinguished by the frost heaves which turn the unpaved roads of Vermont into nearly impassable mires. So there has to be something magical about these roads considering that after all the mud season strife they settle into these kind, gray paths, smooth and gentle as velvet.
Bryan just came off of placing at the New York State Criterium Championships. The rest of us just came from casual group rides and pizza tours. Who's smiling now?
Well, Moi was probably smiling.
Benedict's already had Lyme’s disease twice and shows a blatant disregard for the tick's territory that we Westerners find absurdly bold.
But he is a hardy man, and his frolicking makes for good imagery.
We eventually figured out that the bridge was in fact closed.
Guys… this zone is haunted AF. Add to this the fact that Benedict keeps repeating quotes from the movie The Witch throughout the trip: “Do you like the taste of butter?” or “Do you want to live deliciously?” and he’s saying them in this insidious/satanic voice. Six out of seven of us haven’t seen the movie, but that doesn’t mean we can’t be terrified by his references. Without having seen the movie our imaginations run rampant, conjuring scenes and situations possibly even more horrifying than the film. Plus there are these ancient graveyards with thin and spindly tombstones; they’re nefarious, they’re decrepit. None of them have those pictures of the dead person smiling, a black and white visage on a slab of stately black marble. No, these deals are gothic and imbued with the phantasmagorical. Its obvious they need/require new blood. It feels like they’re watching us. It is all very upsetting.

A Late Afternoon Timber-Pile Picnic

We lunched on a pile of timber that is without a doubt a brown recluse condo development.
This is that Brown Recluse condominium I was telling you about. Lovely right?
Trail Essentials. "Cholula was started by the Harrison family, originally of Chapala, Jalisco, who now reside in Dallas, Texas. The image on the bottle is a portrait of Harrison family matriarch, Camila Harrison. She is survived by son, Roberto Harrison, and granddaughter, Callanita Harrison." ~ Wikipedia

The Post Office Squat of Rowe, VT

We talked shop with a fantasy couple, found the best water in Vermont, and continued our search for Zoar.
By post office squat I mean some sort of hamlet where there is a post office and a few other buildings but no stores, no library, no gas station. It baffles us why and how people survive out here.
We talk to some kid chopping at weeds along the shore of the pond adjacent to the post office. He tells us that we we can get water from a faucet at the post office. More specifically he tells us, “I don’t care if you get water from over there.”
WHO WHO you looking at.
Gahhhhh. This hunk was pretty damned sick for the entire Vermont ride. That didn't stop him looking like this, in that light, for eternity. Dat Moi doe.
Her hubby tells us we can find way better water just down the hill. “Best water you’ll ever taste,” claims the old dude (unfortunately they wouldn't tell us where to find Zoar). He also says he’s been trying to hit 60 miles per hour on this local descent that we’re unfortunately going to have to miss. He’s hit 57 but can’t break 60. I look at these two and they make me want to move to Vermont, they make me want to be old, they move me to tears.
This lady is wearing the best outfit we've ever seen. If you don’t agree or don’t know who I am talking about then there is something wrong with you and I recommend that you change your homepage from to something like,, or
Whatever it was, it wasn't Zoar, so it wasn't important.

Surviving the Hoosac Tunnel

Subterranean trespassing, drunkards in ponchos, and a game of chicken with a freight train.

It should be abundantly clear by now that Poppi was our Wikkid Toouah Shepherd. But here’s the thing, most people think being a shepherd is easy. Carry a stick, don’t fuck the sheep (no matter how lonely you get), or do but lie about it, sit in the shade, read books, follow your flock around, etc. And sure, while grossly oversimplified in many ways that’s a pretty accurate rundown of your basic shepherd roles and responsibilities. That is except for one key error: it’s lead, not follow. That’s right, if you want to be a good shepherd you’ve got to be prepared to lead your flock to water and safety. I.e., you lead—not follow—them away from dangers like wolves, hailstorms and your touched cousin Earl. You have to protect your flock. It’s YOUR flock. You have to count them at night to make sure nobody is missing, you have to care for the weak and the sick, you have to round up those among your flock who are lost even if it’s their fault, especially when it’s their fault. Point is, when you’re a shepherd you’re 1000% responsible for the entire flock, every single individual sheep, and sometimes it sucks. But like, don’t be a shepherd then.

“I am the good shepherd; the good shepherd lays down His life for the sheep.”

—JOHN, 10:11

But what happens when your sheep get a little frisky? What do you do when your sheep tell you, “Hey Poppi, let’s spice this ride up, for example, what about a little bit of light trespassing, or like, what if we found a dead body or something, you know, like Stand By Me the movie starring Corey Feldman AND River Phoenix?” What does it mean to be a good shepherd in a situation like that?

“Counterintuitive though it may be, what if when it’s raining and the light is failing, instead of leading your flock to a State Campground with showers and flush toilets, you lead them into a Haunted (active) Train Tunnel, and what’s worse/better, the whole time you do it under the influence of some woefully-inaccurate Train Schedule Timetables? What. If.”

Well first you need to start selling the idea, nice and sly like. Nice and easy. Yes it IS your flock but even sheep will buck if you let ‘em. Watch and learn folks, watch and learn. What follows is a series of email correspondences from Poppi Wheeler, received during the route planning stage in the lead-up to our Mad Wikkid Campaign. Sidenote, these emails are reproduced here for your benefit in the order they were received, and verbatim.

  1. Dan, I’ve also always wanted to ride my bike through the 5 mile long hoosac tunnel, otherwise known as “the bloody pit”. its the most haunted site in all of new england. ive gone in like 15 feet, and changed my mind 3 times now!
  2. yeah dan, we need to do that. ive been wanting to ride through since i found out about it. i know people walk through… and yah, there are 2 trains that go through each day. loooonnnnggg ones. suppose it would be smart to brush up on the times. the more you read on that place the better it gets. and seriously the spookiest place ive ever been.
  3. id really like to make it to the “hoosac hotel” near the infamous central shaft. im sure you read that story ::::
  4. looks like we can hike in 2 miles to get to it from the west portal of the tunnel. the west portal is way more photogenic. it looks like the drawbridge of castle greyskull, and if approached during the right weather, its spewing fog and gloom. the hoosac hotel, 2 miles in is pretty ramshackled with graffiti and stuff, but it holds the lore. its so goth. sure to make our sweet dark swedish prince nice and jello. the write up on the history of the central shaft and the rest of the tunnel is sure to be a page filler.

I know what you’re thinking. Four emails later and the hook is (clearly) set, but can the Hoosac deliver? Which brings me to my next point, is this big-shot haunted tunnel legit or what? It’s a great question and I’m going to answer it, sorta. What I mean is, why don’t you judge that for yourself? What follows is a brief list of the Hoosac’s bona fides (reproduced here without permission from this site):

  1. The work crews employed to dig the tunnel were probably very miserable. Conditions in a poorly ventilated tunnel with underlit conditions underneath several mountains over 2,000 feet were probably just as you’d expect; horrible. It was described as “building a sandcastle in the mud”. The rock and earth were so unstable and prone to washouts, that the tunnel was either constantly flooding or collapsing. Eventually, they had to dig canals to get the excess water out of the tunnels, which were also often flooded and over depended on.
  2. All and all, the project took 24 years to finally complete, finally finishing in 1875. During this time, an estimated 200 people lost their lives, others walked off the job, and many people including the federal government wanted to pull the project because of the number of horrifying casualties. However, the railroad company played a sneaky card and purposely didn’t report all of the deaths, pushing the number down to around 75, give or take, which caused the government to agree to allow them to continue.
  3. But the most chilling incident to take place here happened inside the central shaft, which alone is incredible – a giant shaft used as a chimney, boring 1,000 feet, or the length of the Empire State Building, down from the summit for better ventilation and exhaust escape. Because coal was the major powering force behind locomotives at the time, the 5 mile ride through the tunnel got dangerous. Conductors were even reported to wave broomsticks out windows to ensure they were still moving, because they couldn’t see through the smoke.
  4. On October 17, 1867, a team of Cornish miners were hoisted down 583 feet into the uncompleted shaft to continue hacking their way down through the mountain. It was said to be a scary ride down, literally into nothing but blackness. But that day, the dark wasn’t their main concern. Flammable chemicals from a naphtha fueled lamp inexplicably leaked and ignited, causing an explosion that ripped through the hoist that was responsible for lowering equipment down, as well as equipment, flaming drill parts, and splintery wood, raining down flaming shrapnel onto the 13 men at the bottom. Air pumps malfunctioned, leaving the men stranded in the dark without oxygen. Those who didn’t die of suffocation, drowned as the hole began to fill with water. Helpless onlookers, realizing there was nothing they could do, waited until their screams stopped bellowing from the hole.
  5. Though it was thought that no one had survived the accident, when they attempted to eventually finish the shaft, they found a makeshift raft, but the man had also died.

So yeah, we were hooked, and the Hoosac WAS legit. When we got there it was raining, foggy and late in the day, perfect haunting conditions! We parked our bikes against the walls just inside the the tunnel’s mouth. About two minutes later, in the middle of getting our shit together for an expedition into the tunnel’s interior, a train came from behind us, in the direction from which we had just come. We all ran out of the tunnel, scared and panicked and pumped. Our shepherd Poppi said that at least now there wouldn’t be another train for a couple of hours. He also said he wanted us all to hike to the bloody shaft pit in the tunnel’s center. Then later, after about 20 minutes of tunnel spelunking, he said he would be happy to simply go to the point at which you can no longer see light at the end of the tunnel.

Tunnel spelunking is gross. The tunnel is full of trash and tetanus. And dripping water. And, of course, ghosts. Also, walking on tracks is not enjoyable. Nobody was too worried about another train because there is plenty of space on either side of the tracks to safely stand against the wall. That said, NOBODY was in a hurry to test the theory. Kyle, Moi and Bryan went the deepest. Poppi, Mary, Sarah and I went the medium. Patrick waited near the mouth of the tunnel, citing respiratory concerns as his reason to not join us. Obviously he was just scared, but it was smoky AF in there.

“It started as a distant rumble and some light vibratory sensations. We were like, wait, is that a train? Naaaaaah, it’s just our imagination. But then it was like, oh shit, that’s a fucking train and we’re like what, a quarter mile from the entrance still?”

Also, the train is coming from INSIDE the tunnel. For a split second there was panic in our group as we all started to run-walk-scramble in the direction of the tunnel entrance. Then I was like fuck-it we’re never going to make it, also there’s plenty of room on edge of the tracks. I think. But Poppi didn’t believe me, I saw terror in his eyes. That’s when he pushed Mary to the ground, jumped over her and shouted, “I’m sorry, I have to save myself, I have too much life to live Mary, I have too much life to live!!!” He ran and he ran and we never saw him again until the train came past and we walked out after it. Watching the train go by from inside the tunnel is a full-body sensation. Also, the first car pushes a whole big wall of train jizz (water, I hope?) and air ahead of it.

After the train incident we all regrouped near the mouth of the tunnel where we met some locals. One of them was super impressed that we went inside the tunnel because he would never go in there because it’s haunted and also because trains, and we were impressed with him because he had no shoes while walking around the spooky entrance of a tunnel the middle of a serious drizzle. And he was on meth. Also, his drug rug.

With the passage of this train, we all assumed we had hours to go play in the tunnel.
Based on Benedict’s intel we enter the tunnel, we’ve got plenty of time to explore. Bene has set the bar: we should walk deep enough into the tunnel that we no longer get light from the entrance.
Okay ladies let's go, time to head back into the salt mines.
To someone, somewhere, this means something important.
"Yes, this is Benedict... oh... how'd you find me? Well yes that is all very flattering... yes I understand... but I am on a trip you see... yes... it can't be helped... you understand I am in a tunnel? Well... yes... you'll just need to tell Mr. West that I won't be able to appear on his next album... yes of course I know that my black metal vocal stylings are without don't send a helicopter... no I am totally fine with flying... no... its just that I promised my friends that I'd be on this ride with them, and what kind of person would I be if I bailed out on them now... yes I understand that Kanye has a schedule... that can't be helped... best of luck with the album, tah tah."
Deep in the tunnel a light changes from green to red. The wind in the tunnel abruptly changes direction. The strong wind that had been pushing us deeper into the tunnel was now pushing against us, the cold breath of a ghost dragon. There is a low pulsing humming coming from the bowels of this hole… “TRAIN!!!!!!!” we yell at the others ahead of us while we scurry to a scooped-out section of the tunnel a few hundred yards closer to the entrance.

The Legend of Barefoot Brad

Our crew encounters BFB and we manage to escape only to set up our tents in fear.
Barefoot Brad is dead center. In that poncho. Barefoot Brad is pretty f*+ked up in this photo.

Returning to the tunnel’s entrance, we are greeted by a young man we would later dub Barefoot Brad (BFB). Dressed in a turquoise, gray, and black drug rug and cutoff pants, BFB is obviously intoxicated. Long story short, Barefoot Brad has done quite a few drugs in his 21-ish years on this planet. A few months ago he went too deep and experienced the sensation of having his face stolen. Apparently this affected BFB profoundly, because he escaped to Vermont with his girlfriend in order to regain his face and psyche. Tomorrow he was set to return to Ohio via Greyhound—we don’t know whether he retook his face. The entire time BFB was telling us his story he was stumbling around the very sharp gravel that had been laid down around the tracks. Bryan mentioned, “Maybe you should get some shoes.” To which BFB retorted:


Well the Barefoot King wasn’t alone: his girlfriend was passed out on the steering wheel of her car a half klick down the tracks, and BFB had been taking in the Hoosac’s splendor with his GF’s mom and kid sister. The mom audibly lamented her lot in life while praising our endeavor, while the kid sister wore the resigned face of the doomed.

It's possible that Barefoot Brad is even more f*+ked up in this photo. It was taken only 10 seconds after the last one, but that's kinda how BFB operates.
The water in this river was curiously warm. Like, downstream-from-a-Nuclear-Reactor warm. It was so unsettling that no one dared take a dip, despite the near perfect temperature.
There is a very real possibility that BFB will show up and murder us in our sleep, so we each clutch our sporks and expandable pumps, ready to defend ourselves in the fashion of our forefathers.

Standards for High-Quality New England Architecture

Feat. Poppi

Stopped under a patch of trees on the edge of a small pasture to wait out a little rain tempest, Benedict educates us on some of the preferred qualities of a New England home while recounting some of the things we’ve seen so far in the day.

#1: Monochrome paint scheme, preferably a shade of white.

#2: Slate roof tiles (the slate heats up and helps the snow slide off the roof).

#3: Basically nothing modern. No Kohl’s. No Restoration Hardware. No Bed Bath and Beyond. NO KITSCH–no little angel statues, no koi ponds, no Tuff sheds, no bay windows (there are no bays in Vermont..why the F*#K would you need a bay window?), no decrepit riding lawnmowers slowly leeching into the earth, no outdoor freezers, etc. Benedict gets visibly upset when he sees these sorts of things. And seeing him upset upsets the group. It’s all very upsetting.

To quote Benedict, "UGH"
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