Driftless 250 in Review

Driftless 250

Team More Bars, Less Hills

“The Driftless 250 is a perfect cocktail of adventure, endurance, local flavor, and a whole love of Wisconsin.”

The second edition of the Driftless 250 was an adventure of the most royal proportions.

Attendees came in from five different states to take on the Drifty and they brought with them varying degrees of preparedness. One hadn’t biked more than 12 miles in a day; one hadn’t been on a bike in 10 years. We had a brother-sister pair, our first all female team, and our first solo participant. True to form, Wisconsin weather didn’t disappoint. 50 degree temperature swings, a hail storm, and blinding sunshine were all present.

Unlike our Pioneer event, no attendees had a broken foot. Also, no teams were brave enough to ride our tandem, Jerry, through the hills of the Driftless Region. That’s a pity but we’ll save that gripe for another time…

The best vacation days I have ever used, and I worked harder than I do at work.
— Lucy and Ethel
Driftless 250 Route - May 2019

Reality Sets In on Leg 1

Nothing brings us more joy than seeing the mixture of emotions on the face of somebody staring down 7 days and 250 miles in the Driftless. It is difficult to distinguish between the laughter that comes from unbridled excitement and the nervous laughter that disguises fear. Questions we overheard at the start line:

Should I have brought bike shorts? How many is too many AlpineAire’s? Does anybody have a map? Why is my tire bent? Which way do we turn when we leave the park? Where’s Keegan?

When the air horn blew, teams lumbered out into their journey the way livestock cautiously sneak through a gate left open. One person went first, a few others followed while looking over their shoulder, and the rest of the teams strapped down their bags and wandered their way out onto the pavement about 20 minutes later.

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Lucy and Ethel astutely describe their situation on day 1:

“We are lost and have a flat tire.”

The first 3 hours brought about a visit to the bike shop for a bent rim, a counter-clockwise navigation of Lake Mendota, team “More Bars, Less hills” stopped at a bar at the 10 mile marker, and Blarence ate his entire ration of RX Nut Butters. There was a quest for fishing licenses that took over an hour and team Backwards Bikeseat stocked up on more beer than one bike could handle.

The most appropriate start to the Driftless 250, however, came from Lucy and Ethel. 20 miles into the trip they took a wrong turn while trying to find Transition number A. Somehow they found a long, straight gravel road straight out of a horror movie and to double down, they decided to get a flat tire on it.

Leg 1 came to a close with team Kileyboo and Blarence completing the slowest bike-to-canoe transition in the history of the Drifty. Two independent observers confirmed that it took them over two hours to place their bags in a canoe and then set off on the river. Some teams arrived at the transition after them and pushed off into the river before them. Was it nerves? We may never know.

All of this happened before the first canoe touched water.

Sunshine on Leg 2

The teams set off down the hardest working river in the nation on canoes loaded with gear and campfire wood.

I sat on and ripped my paper map the first day on the river.
— Sam of Team Backwards Bikeseat, stating the facts

The first night on the water, some teams found themselves camping in hammocks as temperatures dropped to a balmy 34 degrees Fahrenheit. If you think that sounds miserable, that’s because it is miserable. The only thing keeping them warm was their AlpineAire pasta and whiskey. Not to disappoint, temperatures and morale soared on subsequent days which left our hearty adventurers contending with sun burns. Other notables: temperatures hit a high of 80 degrees Fahrenheit, one fish was caught, participants got acquainted with pooping outdoors, one team fashioned a sail out of a garbage bag, and the bald eagles in the bluffs kept their watchful eye on the teams.

On the second day on the river Han Solo reported that on his 45 miles of paddling, he saw over 5 bald eagles, a flock of 17 pelicans, and not a single human. If that doesn’t push your buttons, you’ve spent too much time in the city.

Click, tap, or swipe to see the teams in action


The last evening on the water, two teams paddled a mile upstream on a tributary that feeds the Wisconsin River in search of a bar and aloe vera. They got much more than they paddled for and what followed was a seven layer salad of the most Wisconsin proportions.

No amount of training, planning, or imagination will prepare you for what you find up the Kickapoo.
— Team More Bars, Less Hills

Through some series of phone calls between a gas station attendant and locals they found a bar that was open.

They were plied with beer, frozen pizza, got schooled on the ways of the river, and then one person of team Backwards Bikeseat got completely lathered in white vinegar by a local woman as a remedy for sun burn. How this exactly happened, why she had 2 gallons of vinegar in her truck, and how it feels to have white vinegar applied on top of aloe, on top of sun screen, is a story for another time. All we know is that they showed up at the Transition number B reeking like a jar of pickles.

Flat Tires Rule Leg 3

The third leg of this adventure is where things really got interesting. Having just endured near-freezing temperatures, sun burns, beautiful campsites and awkward treatments for their maladies, the teams reached Wyalusing. At the transition they looked as if they’d been at sea for months.

The teams scattered off into the Driftless area within hours. Some wouldn’t be seen until the finish line. The nonsense that resulted on dry land is best described in a series of facts:

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Blarence, with some advice to future attendees

“Remember, there will always be another hill.”

  • Most miles biked in a day: 135

  • Least miles biked in a day: 4

  • Lucy and Ethel racked up a total 4 flat tires

  • More Bars Less Hills successfully plotted the least hilly route through the Driftless region

  • One night spent at a farm/commune/hostel/place.

  • One cow was milked

  • 7+ miles pedaled with a bike seat on backwards

  • Two pints of fresh milk drank straight out of a cow tank

  • One team camped in a pasture

  • 4 trees in a local man’s back yard saved the night for two hammocks

  • Hitchhiking happened; exact trip count varies on who tells the story

  • One team was invited in a house while wearing a garbage bag as rain gear

  • One free ice cream cone served up in Montfort

  • Blarence and Kileyboo clocked 50 miles of hills in a day

Click, tap, or swipe to see the teams in action

Fittingly, the finish line was just as unexpected as the 250ish miles that lead up to it. Han Solo finished three days early. Team Backwards Bikeseat finished at the Madison Airport by biking right up to the terminal and getting onto a flight. The rest of the teams finished on Saturday within 30 minutes of the finish line time, each approaching from entirely different directions and with entirely different stories of their time in the Driftless.

Job well done.

Jacob Gafner1 Comment