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We believe in a good adventure. The kind of trip that challenges you and has more unknowns than most people can stomach. It’s a different kind of travel, and we think more people should experience it. Sign up for our next trip to taste it yourself.

The Driftless 250

250 miles, 7 days, Bike + Paddle + Camp. Across the beautiful Driftless Region of Southern Wisconsin.

Late Summer Edition

Sept 07 - 14, 2019

Spring Edition

May 16 - 23, 2020

“The Driftless 250 is what I imagine going through the laundry is like. You get kind of dirty, then get sort of wet, then you kind of get the shit kicked out of you for a little bit but at the end you have this really warm and fuzzy feeling and you want to do it again.” - Walker

Sponsored by our adventurous friends at:

Driftless 250 Sponsors



Late Summer EDITION: Sept 7TH - Sept 14TH, 2019

  • Kickoff Party - Sat, Sept 7th - Downtown Madison, WI

  • Start Line - Sun, Sept 8th - ???

  • Finish Party - Sat, Sept 14th - Middleton, WI

What’s included?

The entry fee of gets you…

  • 7 days of beautifully unscripted travel

  • A mostly sea-worthy canoe for your whole team

  • Paddles and life vests for your whole team

  • At least one bald eagle sighting (We stopped counting at 20)

  • One week’s worth of RX Bars and nut butters courtesy of RX Bar ($25 value)

  • One week’s worth of backpacking meals and more courtesy of Alpine Aire ($100 value)

  • Transportation and secure storage for your bike while you're drifting down the river

  • We’ll even throw in some fire wood for you

  • A start line party (food + drinks)

  • A rager of a finish line party (food + drinks)

  • Shiny piece of metal to commemorate it all

  • Satisfaction that you're helping preserve one of the most beautiful areas of the Midwest

  • Stories your coworkers will drool over

What do I need to bring?

You must bring your own bike (It’s BYOB). You also need to bring your own camping equipment; we recommend you pack light. Don't bring more than you can carry on a bike. Click here if you want help with outfitting.

You will need to bring/buy your own food and water but our sponsors have done most of the heavy lifting for you. You’ll never be more than a few (dozen) miles from civilization so if you’re running low on cheese curds you can stock up pretty easily.

We also recommend you bring a bring a map and compass. Don't bring GPS unless you want everyone to laugh at you.

If you’re traveling from far away (Toronto, San Francisco, or other faraway lands) and need help coordinating a bike rental let us know and we can help, we’ve got a bike guy. 

The Driftless 250 | The Drifty | Wisconsin River