A 310-mile ride will chew you up and spit you out. No matter how much I told myself to cool my jets, keep the powder dry, not go into the red, and any other metaphor with the message “Ted, don’t ride too hard too early”, I had a tough time doing so.

Let’s backtrack. It’s 11pm on Saturday night at the end of a dirt road in way way northern Vermont. There’s a steady pelting rain as I make the checks to my gear, lights, computer, clothes. If we started trudging through the woods north past where the road ends, we’d meet the Canadian border in a matter of minutes. Instead, I’m about to set off south to the Massachusetts border. 310 miles of pedaling are ahead of me, 90% of it is gravel, where the pre-ride mapping software tells me features 31,000 feet of climbing, but it will actually tally just shy of 35,000 feet. I’m as fresh and ready and eager as ever. Time to get #DIYgravelDK going!

Rain pools on my computer screen already bright with glare from my headlamp, so I have a hard time taking the information in. Anytime I get a clear reading I’m pushing power just shy of threshold. It feels easy. Weird. Is it calibrated? Yup. I guess I’m just itching to go. The climbing starts from the very get-go and the road deteriorates from “tame gravel road” to “backwoods of rural Vermont” quickly. Really quickly.

I’m an early-to-bed, early-to-rise kind of guy, so setting out at 11pm is well past my bedtime. I took a nap Saturday afternoon, May 30 — Dirty Kanza Saturday. Those will be the final 90 minutes I’ll sleep for the next 33 hours. I’m so brimming with adrenaline (or coffee), though, that I’m also wide awake here in the early hours of Sunday. In any other context, namely if I were off my bike making my way through this heavily forested woods, I’d be spooked. The way my handlebar light shoots a cannon of light forward, bouncing off puddles and into the woods feels like an eerie black and white kaleidoscope miles from any civilization.

The first six hours are pure novelty. I’ve ridden at night, I’ve ridden in the woods, I’ve ridden in the rain, I’d ridden in ferocious wind. Throw them all together, however, and this is something unlike I’ve ever experienced. The rain increases as temperatures drop. At the top of every climb where the wind is the most intense, it’s no wonder that there are trees down sporadically across the rough gravel road. There’s so much climbing, in fact, that my estimated 15mph is optimistic. It’s slow on the uphills for obvious reasons; I’m slow on the downhills because the roads are harrowing in the best of conditions, made all the worse with the weather.

The sun is still behind a wall of clouds at sunrise, but it lights up the world as I roll into Ian Boswell’s driveway somewhere around 6am. He has hot coffee and Pastry Chef Boswell has even prepared sausage cheddar muffins, where I take five minutes to warm the mind and soul. I feel like this first 100 miles of riding in the wet darkness are a closed chapter with nothing but sunshine and tailwinds ahead.

And then we start climbing.

Here I am 7 hours into the ride when I meet a fresh-faced, fresh-legged Ian. I bite my tongue as we go up and down and up and down and up and down on ever deteriorating roads.

Mind you, this is not a complaint whatsoever. This ride is breathtakingly beautiful. I’m just the nincompoop who decided to link the start and finish together in one fell swoop. It was originally designed to be done over four to six days.

It’s somewhere around my tenth hour on the bike that Ian says, “Geeze Ted, this route is super hard!” I breathe the biggest sigh of relief of the day. It’s not just cumulative pain that has me deep down Struggle Street here in the heart of central Vermont.

This route is the brainchild of Joe Cruz. Joe and I were distantly connected, but I knew of his mapping prowess and penchant for an adventure — plus his Vermont citizenship — when I reached out to ask if he’d ever connected the northern border of Vermont to its southern border… on gravel. It’s a dirty-200-on-100, if you will. He hadn’t, but that sent him on a mission.

Joe is meticulous and doesn’t just study ridewithgps.com, but searches public town records for the best public access roads — ahem, “roads” — available. It’s no wonder his hobby is at bikepacking.com, but his career is in academia.

I say goodbye to Ian, who’s in for a century of his own, at my mile marker 142. Sweet, not even half-way done. I take the advice that’s been barked into an earpiece in Pro Tour races all throughout my career, “Eat and drink, eat and drink, eat and drink”. Over the next thirty miles as I roll into Sharon, Vermont where I know my wife Laura and baby Hazel are waiting for a quick hello, I slowly come back to life.

To be honest, the next hundred miles are a blur. No matter how much momentum I get going, I can’t break 15mph. The climbing is relentless. If the hills ever get shorter, that just means they’re steeper. The one definite standout of this section is that people are out. I’m broadcasting the route with a traceable Garmin inReach, so a few dozen people are out in their front yards, at intersections, or join me for a pedal down the published route for a mile or five. If that doesn’t raise my spirits, honestly nothing will.

The longest climb of the day is about 260 miles into the ride. A six mile snowmobile trail, this path is rutted, doesn’t see much traffic, and is so bumpy that it’s pretty much suited for a full suspension mountain bike. Or, thankfully, the Cannondale Topstone Lefty beneath me. That’s a take-home message over the entire day: this route is burly and were it not for the plush Lefty up front, the Kingpin in the rear, the fast rolling 48c Rene Herse tires, the 46t x 10-50 SRAM drivetrain, to be perfectly honest I don’t know how I would have gotten through this ride. Certainly not in one day.

Up and over, down the final climb, a lightning fast six-mile descent, never has the final 10% of a ride felt so far. And so tantalizingly close. 30 miles to go, two bumps in the road, plus one pitch that’s much more significant. I’m well past my 8pm estimated arrival. Thanks to the tracker, more and more people are out cheering me on. A few cars shuttle ahead of me where people pop out, cheer, hop in, shuttle ahead, pop out, cheer; there are uplifting signs on the road, there a half dozen people who join me to pedal lengthy stretches at a time. I really can’t think of a time that company on a ride has been so welcomed. I know I’m not up for deep conversation at this point. I’m sure my exchanges are brief, but especially looking back in hindsight, everyone is so friendly. If you rode with me on this ride, and especially in the final few miles, thank you.

There’s a 20mph sign at this sliver of the Vermont/Massachusetts border. Directly on the other side of the road is a big marble slab that denotes Massachusetts on one side and Vermont to the other. Based on messages I receive later in the day, there would have been more people out if I had arrived as my estimated 8pm. It’s now well past 10pm and still a handful of people are there to cheer me in. I’m empty. I’m sleepy. I’m hungry. I’m at a loss for words. Also based on the messages I receive that day and dozens more the next, I’ve offered up a bit of light, a welcomed distraction in an otherwise sad day. That’s entirely unintentional as I’ve had this ride planned for weeks, but I won’t deny any fringe benefit to a bike ride.

Superlatives are a strange thing when they’re subjective. Is it the longest ride I’ve done? Sure, absolutely yes, by nearly 100 miles. Is it the hardest? The worst? The best? The coolest? The gnarliest? All good questions. I’ll tell you what, Paris-Roubaix is hard. Dirty Kanza is hard. 200 on 100 is hard. #DIYgravelDK is definitely in the running for hardest. This ride was, perhaps, the most legendary.

—All photos @NickKeating and @AnselDickey of @VermontSocial. Stay tuned for the King of the Ride video. It’ll be one for the ages.

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