It appears the Kraken requires tribute: rubber, sweat, ejected water bottles, sealant, the footbed of my cycling shoe. Some of these you’re happy to give up and continue; some of them you’ll really miss but don’t become ride-ending sacrifices. But most often your ride gets ended, one way or another. The story goes that only a handful of people have been able to finish the entire course — a mere ~100k — and we, alas, would not go on to join that number. At least not this time.

The Kraken is (generously) a gravel route (but really more a mountain bike route) that runs a loop of the surprisingly bountiful trails, gravel, and dirt roads running from one end of Martha’s Vineyard to the other. The route is neither published or marked, but if you go down to Edgartown Cycles and ask for Jon, chances are you can find it. It’s a rather ingenious string of connectors, leaving you riding on actual pavement for maybe only 5 miles or so total. The elevation profile is deceiving: it is both less and more climbing than you think it’s going to be. Much of the climbing is short, steep off-road sections like you might get in a lot of parts of New England, and it is not their length but their relentlessness that gets you, slowly sapping the spring in your legs and making you happy you brought a bike with gears.^[1] You climb up to the highest point on the island and then down a valley over to climb up to the second highest point on the island. You charge through the woods and sprint for town lines on gravel. You even get to practice your cyclocross a little on one of the many short sections of sand (as it is, after all, and island). The trails are alternatingly rocky and rooted and flowing. I was riding knobby 700x40c (measured) tires and they were frankly not always enough.

My friend (and former boss)^[2] went down to the Vineyard during his April break to moonlight at the bike shop, since it’s still a little early for the seasonal folks to arrive ahead of the summer. Alex is a wizard on the product and ordering and organization side, and I…​ am capable of counting things.^[3] I more or less ran around counting the things Alex told me to count, and it was a lot like the old days, working at the shop in the North End, except now we were working for Jon instead of with him (thankfully, a remarkably easy transition). We were down to ride bikes and take what for us amounted to a vacation and hang out with our old friend and help out around the shop. All these things were achieved. We drove down, parked, and rode our bikes to the ferry in Wood’s Hole and then down to Edgartown from…​ whatever town the ferry let us off at. The weather was mostly cool and gray but we didn’t get rained on too much, a minor blessing since I still had yet to replace the fenders I’d accidentally destroyed near the beginning of the year.

We arrived at the shop and more or less immediately got to work, and had a lovely, raucous evening afterward. The next day was more of the same but we began discussing what we might ride on the subsequent day off when the shop was closed. Alex was down for gravel, I was in it for the miles (as I had the first 200k of the season to prepare for the following weekend),^[4] and Jon was down for anything. Alex had heard whispers about the Kraken and suggested it to Jon.

"You want to do the whole thing?"

"The whole thing."

"You sure?"

"Why not?"

"If you do it, you two will be maybe the fourth and fifth people to complete the whole route."

"Sounds fun," I said. At this point in my life, 100+k doesn’t seem to daunting a distance. It would only occur to me an hour or so in the following day that it had been a long time since I’d ridden that distance off-road.

So we planned. Loaded a version of the route into our bike computers. Ate heartily. Filled bottles, slept, and woke up far too early the next morning to do the supply drops, since there was no reason — no need — to go into town if you didn’t have to.

And then once we’d had our coffee and breakfast and all bodily needs taken care of, we were off.

I wouldn’t consider myself a bad off-road rider, but I would also not consider myself particularly skilled, either. When I go play "mountain bikes" with my friends I’m riding the Wednesday, a fat bike, whose 4" tires more than make up for most of my deficiencies in skill. I do like to take the Straggler on the local trails from time to time, and I’ve even lately taken to taking the fixed gear off-road, but I’m still no mountain biker.

Jon, on the other hand, is very much a mountain biker, and made the wise decision to ride a carbon mountain bike, whereas Alex and I were on steel gravel/rando rigs.

The weight of the bike was never really the problem, nor was the gearing (though I did notice that my right shifter didn’t always hold the same tension after larger drops or hits), but lord was I beaten up by the roots and rocks. I tend to run my tires too high, too, which doesn’t help. My shoulders, arms — I got a very different kind of workout than what I’m usually treated to on the bike. But it was smiles for days once we got out there. I felt strong and the legs were good. The pace was steady. Despite it being silly to have a box bag on an off-road ride I was happy to have my snacks handy. We stopped for pictures.

And then the trails got a little more challenging. I battled pedal-strike. I hit a rock and heard a crack. My pedal felt a little odd, or rather my connection to it. I noticed a little more flex in my shoe.

We finished the trail section and stopped for a snack. I asked Jon if you could crack a carbon footbed. He said sure, he’d done it plenty. So I looked. And there it was:

These shoes were, I believe, the last things I bought on "pro deal" when I worked at the shop in the North End. They were really, really good shoes, and they don’t make this model anymore. Rest in peace, old buddies.^[5]

It was turning out to be a good, hard day out on the bike. We did a little more road, had made it successfully more or less all the way across the island, and dove into the next trail section. Ambling along nicely. Alex and I walking our bikes on a section that very much could not be ridden on the bikes we were riding (or: at least not by us, and I feel no shame in saying that).

Then a hiss.

Alex and I have debated tubeless for on and off road for a long time. He’s a fan of tubes, and in large part I agree with him: they still work just fine, they make changing tires easier, there’s no mess, setup is simple, and they’re easy to change. But sometimes they’re not easy to change. Especially when you’re running a tight-fitting tubeless tire on a tubeless rim, like he was. I think he’d even talked about switching over to tubeless the night before but we just hadn’t gotten around to it. So we stopped, and Alex picked the thorn out of his tire.

Unfortunately it proved hard to get a new tube in there without pinching it there at the end. I think adrenaline probably had something to do with it (I know this happens to me when I’m trying to fix something out on the road or trail: you’re jittery trying to get it done fast), but mostly I think it’s just fucking hard to fit tubes in tubeless stuff sometimes. Especially in the middle of a trail. Tubes were pinched, patches didn’t hold (and I’d stupidly left my good patch kit back in Boston), and Jon made some calls to find us a ride out of there.

The kraken — and its thorny bush sections — had won.

The wonderfully kind friend of Jon’s who came to the rescue had a two-bike rack and I kind of wanted to ride back anyway. I found a roadish route via the magic of smartphones(tm) and had a very nice, if upwind, ride. Alex and Jon waved at me when they passed me on the road.

I’m pretty fucking extroverted but it’s also good, especially on trips, to take some time to yourself, and the ride back provided for that amply. I thought about the randonneuring season ahead, which wasn’t maybe going to be the season I’d planned for but a good one nevertheless; I thought about work, the work I was doing at Edgartown Bicycles, the shame that is modern labor economics; I thought a little about the novel but not enough, if I’m honest; and I thought about the morning’s ride, about its challenges and triumphs and just how it had been so much fucking fun.

I think all told we did about a third of it. We would go on to ride a reasonable amount of another third the following morning, and I was a little bummed that we didn’t have another free day to try it again (not that that would have been a good idea at all, given the very hilly 200k I was going to do that Saturday). But we’re going to find time to go back. Give the whole thing a go again. Alex might bring his mountain bike. I might set up singlespeed, because why the hell fucking not. We’ll come back and do the whole thing. All of our tires will be tubeless. We will carry plugs and sealant. I’ve no doubt we’ll nevertheless have things to give up along the way — more skin, if nothing else, if I don’t learn how to take sandy corners more competently — but we’ll return. Do battle. Succeed.

(And have a rad fucking time: of that I have no doubt.)