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300 Miles on Drifty No. 3

Well, shucks. We’re going to have to throw out all of our Driftless “250” signs. On the 3rd edition, teams got their miles worth by pedaling and paddling for more than 300 miles. This is exactly the sort of effort that makes us blush. What started as a double-dog-dare to get teams to struggle their way to Beer’s Hometown in Potosi, WI, resulted in a rather respectable ramble through southern Wisconsin.

Chief of the Lost Trumpet Corps, rallying the troops.

Chief of the Lost Trumpet Corps, rallying the troops.

This September’s Drifty was held exactly one year after the inaugural trip of Lost Travel and it turned out to be an anniversary celebration of the most hilly proportions. It started by welcoming the participants with libations and a salute to the team that traveled the furthest. In this case it was Mr Mojo and The Ripps who flew in all the way from Alaska to punish themselves in the Driftless Area. That record is likely to stand until we fire up our marketing efforts in Brazil.

The expedition got underway with the half-formal pomp and circumstance that teams have come to expect from the Drifty.

As the five minute countdown was sounded by the Lost Trumpet Corps, teams moseyed over to the start line. Some were still packing bags, some were nursing mild hangovers, and at least one person was staring at their bike as if it had done something wrong. Then “Reveille” blared from the bell of the trumpet, the airhorn was raised, and poof. The annoying honk we were hyped up for was replaced with a spurt of white smoke. The trumpet corps recovered by playing a quick fanfare and a few people yelled CHARGE! Laughter subsiding, the teams looked left, then right, and then walked/biked their way off into the streets of Madison.

A great way to sample the Driftless area at a pace that is challenging enough to be satisfying but still leaves enough time to enjoy the scenery and do some exploring.
— The Ripps, basically summing up the entire trip while politely leaving out a mention of the thunderstorms.

For the first time, teams took a southerly route through SW Wisconsin.

For the first time, teams took a southerly route through SW Wisconsin.

They pedaled into the Driftless region under cloudy skies that only Londoners could love and The Brewery Challenge played a role from the minute the trip got started. We honestly thought Luftegrof was lost after only two miles in but it turns out he was actually plowing his way through a detailed, 12 brewery route, that had been plotted on a map.

Luftegrof’s brewery planning map dubbed the “SPS” (Sharpie Positioning System). With this level of precision and preparation, we should have asked him to solve a cold case.

Luftegrof’s brewery planning map dubbed the “SPS” (Sharpie Positioning System). With this level of precision and preparation, we should have asked him to solve a cold case.

A few other notables from the first few days on the trip:

  • 6 attendees got lost before the race even started and almost missed the starting gun.

  • We learned a new way to carry a canoe (Between your legs?)

  • “If I have a red bull right now, I’ll sh*t my spandex.” – Penguiño refusing additional caffeine at the Start Line

  • Mr Matt lugged an iron anchor along on his bike ride because he was the last person to sign up for the Drifty and he was late to the kickoff party.

  • “Well, I’ll see you Wednesday I guess.” – Mr. Griep unceremoniously surrenders his bike at Transition Number A.

  • The Missouri Tavern got its usual rush with thirsty bikers, minutes after opening its doors

  • The age-old debate over which end of the canoe is the front continues… more than one team got into their canoes backwards.

An incredible trip where you’ll learn more about yourself than you anticipate. The perfect combination of relaxation and exertion.
— Penguiño

Photo credits go to our hearty adventurers.


The rest of the trip was quite literally a blur of thunder, lightning, sunshine, and rainbows. Mother Wisconsin gave it her all. These teams battled the worst weather on the Drifty yet, and they did it with smiles that didn’t fit the misery they had just been through. To go through that amount of thunderstorms and come out smile, you’d have to either be delirious, drunk, or have a few spokes loose.

While getting stomped on by a thunderstorm on night two, Mr. Penguiño began running around on an island doing a top notch Lieutenant Dan impression while trying secure the rain fly on his and Mr Griep’s hammock.

You’re the first human’s I’ve seen all day.
— Mr. Matt, paddling up to Transition Number B.

A smattering of other stories from the field:


Mr. Matt:

“You’re never too old to crash your bike.”

  • Team Ripp got dealt a shit canoe at the start of their adventure. “I never had such a poor handling canoe or one built with so little legroom for the person in the bow” we heard from Fred. After a frustrating 5 miles, they were about to start penning a letter of discord to the organizers until they realized they were sitting in the canoe backwards. Team Ripp is reportedly much happier now.

  • Bald eagle sightings crossed into the double digits.

  • The Alaskan Contingent became the first on a Drifty to enter the metropolis of Lancaster.

  • One of the nights, teams found refuge at a town with a Bar-Gas Station-Campground-Farmer’s stand combination that only Wisconsin could produce.

  • Luftegrof sprained his ankle on a sand bar. The details are a bit misty but it had something to do with excitement and firewood and an impending storm and, well, Luftegrof just being Luftegrof.

  • The Drifty transcended borders as Penguiño and Griep dodged barges to paddle across the Mississippi and set foot on the shores of Iowa.

  • One night a few teams hunkered down at a bonafide campground on land where the going rate for a hot shower was 8 quarters for 5 minutes which isn’t terrible except nobody remember to pack their change jar on the trip.

  • Clever new names were appointed to islands based on the activities that have taken place on them. Our favorites are “Lightning Island” which got a lighting show from Zeus himself and “Poop Island” which… well… you get it.

  • Camaraderie and solitude both played a part on leg number 2 as teams grouped up and separated over the 3 days like an accordion. This carried into leg number 3.

  • Tom said “You can tell the people who plan to bike a lot by how well they pack their bike” while glancing at his unkempt bike.

  • Teams took a liking to our new ‘check-in’ feature on the tracker by sending cryptic messages back to Lost HQ including: “Literally the only open bar in Muscoda,” “Soggy Subway,” “Luck of the Irish,” “Daddy’s Dew Drop Inn,” and “Anchor’s Down.” We’re pretty sure there’s a story behind each of those.

  • Mr Matt crashed his bike, all alone, and his top heavy backpack pulled him down into a ditch. He ripped his shirt, got covered in mud, and then spent the next hour laughing at himself as he biked along. THEN, he told us about it so we can publicly ridicule him.

  • Luftegrof put his entire bicycle in the shower because it hasn’t gotten enough rain over the past two days.

  • The New Glarus Brewery got it’s first Drifty visit as did Wisconsin Brewing company (the finish line of the original drifty).

The back half of the Drifty saw some serious mileage and even more serious hills. Teams christened the hills of miner country with their tires (and footsteps… at the finish line we heard sheepish confessions of walking up hills). Yes, there were a few flat tires but nobody seemed phased by them; much like the rain, lightning, and trees in the road they all encountered. This was the most challenging Drifty yet and you wouldn’t have known it from the smiles at the finish line. As for the Brewery Challenge, Luftegrof won handily. He clocked in a whopping 21.5 breweries over the course of the week. The “0.5”? A winery.

We’ll leave you with some poetry from the Veterans:

“Bike up hills. Camp in rain. Kayak in sun. Turtles on log. Birds in trees. Bugs in ear. Sand in tent.”

“Turtles sit on logs, cows are afraid of bikes and lightning storms in a tent are really loud.”

“Drifting down the Big W and rolling the hills of the South West made for the best way to experience what one of the best regions of Wisconsin has to offer!”

”Don’t camp in a hammock. On an island. During a severe thunderstorm.”

They did it. We had our doubts, considering the fact that less than half of them successfully found the start line, but they turned out to be a more than capable bunch of drifters. They were given medals and have now earned their rightful place in the halls of Lost Travel Veterans.

9 people went into the Driftless area, only 7 came out.

9 people went into the Driftless area, only 7 came out.

The event taught me to enjoy the small towns, local taverns, back roads and sleeping outside.
— Team Coleman

Sound your like your cup of beer? The next two Driftless 250’s are on sale now.

driftless 250

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