The Driftless 250

By now, you might’ve heard of The Driftless 250 (also known as The Drifty 250, an alliteration we aboulutely love), a 250-mile, 7-day, bike, paddle and camping event.

What started as a small group of friends out on an adventure became a twice-a-year event located in Madison’s own backyard. It also inspired a business. We recently got acquainted with Jake from Lost Travel, an adventure company that him and his wife, Larissa, created after the inaugural event. There’s a great article here for more on that backstory. Lost Travel also creates/curates multi-day events for adventurous souls outside of Wisconsin.

Here’s how Lost Travel describes the Drifty:

“The Driftless 250 is a 7-day, unsupported adventure that takes place in the beautiful Driftless Region of Southern Wisconsin. It’s like a triathlon, kinda. There is some biking, but no running. There’s camping, there’s no route, and you only have to swim if you fall out of your boat. So, nothing like a triathlon. Grab some teammates and come get lost for a week. You’ll help raise money to preserve the environment while you’re at it. Money from this event goes directly to organizations that help preserve the Wisconsin River for future generations. When it’s all said and done, you’ll have some kickass stories that’ll make your coworkers jealous.”

For a little more insight on the trip, here’s an entertaining interview with Jake on what to expect, which is the unexpected. When we first heard about the event, we joked about it being quite possibly the worst bike-shuttle we’ve ever heard of. To which Jake replied, “It’s also been called “the best way to start a terrible bike ride,” “miserable,” and “the best and worst week of my life, at the same time.” That cracked us up.

That said, it’s a crazy unique event and surely to be a memorable experience – because as we’ve learned, it’s the unexpected stuff that happens during our own paddling trips that make them memorable (for better or worse). Best yet, by participating you’ll help raise money to support the River Alliance of Wisconsin, which we think is an extra special benefit since we’re quite smitten by the work they do.

If you’re interested or know somebody who might be, the fourth iteration of the Driftless 250 is set for May 2020 and signup is already underway. There will also be a fifth in late-summer 2020, but the dates aren’t finalized just yet.

The Driftless 250
May 16th – May 23th, 2020
General Info Here

Some Photos to Love of The Driftless 250:

“The Driftless 250 is what you make it. If you want to drink good beer, eat morels, milk a cow, stay in a communal farm, play mario kart, and join a tractor parade… the Drifty has you covered.”

On the Wisco…

“You will get no cheers for finishing first because it’s not a race. Last place will probably have the best stories.”

“Being present requires patience and reminders, but is worth every second in this crazy world we live in.”

“On the Driftless 250, some teams didn’t carry a single source of water. Not much need for it when you’re floating on the Mississippi River with a BeFree bottle.”

“The Driftless 250: Voted the best way to start, and end, your Summer.”

“This Drifty has put teams through the ringer. Or rather, teams have been wringing out their clothes because they get rained on every day and sleep in flash floods. Sound like fun?”

“A beautiful sunset on the Wisconsin River.”

Relaxing at Wyalusing State Park.

“Reason No. 14 to do the Driftless 250: Waking up with no other purpose than getting from point A to point B.”

Not a bad bike lane.

“Train > Bike.”

“Sage advice from a Driftless 250 veteran.”

“The level of fitness for the trip is a matter of personal preference. The hills of the Driftless Area are no joke but we have had teams take them on with little more than blind ambition and curse-words.”

“That pretty much sums it up!”