The Driftless 250

The Driftless 250 is a 7-day, unsupported adventure that takes place in the beautiful Driftless Region of Southern Wisconsin.

Funds raised from this event go directly to supporting the River Alliance of Wisconsin.

Funds raised from this event go directly to supporting the River Alliance of 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.

The Driftless 250 is supported by these excellent organizations:

Driftless 250 Sponsors

Driftless 250 Testimonials

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
“Prepare to experience American culture while torturing your back and ass. Best week of your life!”
— Brent
...expected the paddling portion to be a little more leisurely but we were constantly paddling for 5-7 hours per day in between a lunch or piss break. And I didn’t realize there were so many fucking hills in the Driftless on the biking portion. I also thought there would be more gnats.
— Jerry

Entry Fee

What do you get for your money?

  • 7 days of beautifully unscripted travel

  • A mostly sea-worthy canoe for your whole team

  • Paddles and life vests for your whole team

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

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

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

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

  • We’ll even toss in some wood for the canoe portion

  • A start line party (food + drinks)

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

  • Shiny piece of metal to commemorate it all

  • Donation to River Alliance of Wisconsin

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

  • Stories your coworkers will drool over

Unroute - The Drifty

The Unroute and Dates

Spring EDITION: May 16TH - May 23rd, 2020

  • Kickoff Party - Sat, May 16th - Downtown Madison, WI

  • Start Line - Sun, May 17th - ???

  • Finish Party - Sat, May 23rd - Middleton, WI

The Driftless 250 will start somewhere in Madison, Wisconsin, USA. The exact start line is a secret but about a month before the event we'll mail you a hunk of wood with the latitude and longitude engraved on it.

There will be no arrows to follow or mile markers. We recommend you bring a compass so you have something more to go on than, "I don't know, maybe that way?"

After the starting gun, the event has three legs:

Leg 1: Bike from the start line to somewhere near Sauk City. The route you take is up to you. This will take less than a day if you're a less than average bicyclist. (~25 miles)

Leg 2: Canoe down the Wisconsin River to the Mississippi, at Wyalusing. Again, the route you take is up to you but we recommend not paddling against the current. This leg could take 3-4 days. 8, if you lose your oars and have to paddle with your hands. (~100 miles)

Leg 3: Bike from Wyalusing to the finish line. The route you take is up to you. By this point you should be a pro. This leg is probably 2-3 days; more if you paddled fast, less if you paddle slow. (~125 miles)

The finish line details are a bit of a secret, but we'll tell you at the start line. It'll be somewhere near Madison, Wisconsin, USA and you'll be greeted with a cold beer.

Support (or lack thereof )

This is an unguided and unsupported event. If you get lost, get a flat tire, fall out of your canoe, or run out of rum, it's on you to figure it out. You carry your own gear, plan your own pace, forage for your own food, dig your own toilets, etc. Things might go wrong. That's the whole point.

The only support we'll provide is:

At the end of Leg 1, we will collect your bikes and issue your team the canoe. We'll then store your bikes.

At the end of Leg 2, we will collect the canoe and give you your bike back.

Other than that, you are literally on your own. Watch out for bears.

The fine folks at Wisconsin Canoe company are helping with the logistics.

The fine folks at Wisconsin Canoe company are helping with the logistics.



You must bring a bicycle for each team member and any necessary safety equipment for biking. You are also responsible for bringing the necessary camping gear to survive in Southwest Wisconsin for 7 days. We offer outfitting services if you fancy or just want some pointers on what to bring.

We'll provide you with a canoe, paddles, and life vests. We'll take care of all the logistics (see 'Support' above) for the bike, canoes, etc.

Additional questions? Ask a Pioneer or our crew at

It’s a unique journey with amazing people where you brave the elements, test yourself physically and mentally, and get drunk with the locals.
— Farshid

Questions People Ask

  • Can you help me find a teammate?

    • Yup. There are plenty of brave souls out there looking for a partner. Post a note on our facebook community and we’ll help connect you.

    • Worst case? Just show up at the Kickoff Party and act friendly.

  • Is this a race?

    • No. You will get no cheers for finishing first. Last place will probably have the best stories. Just try to finish before the snow hits. Wisconsin gets chilly in the winter.

  • Seriously, where does the race start?

    • Seriously, we will mail you a chunk of wood (probably cedar) with the latitude and longitude of the start line carved into it. You'll receive this about a 4-6 weeks before the event starts. Plan on being within 10 miles of downtown Madison, WI, USA on the day of the kickoff.

    • If you're flying in, book tickets to/from MSN (Dane County Regional Airport). You can also catch a bus up from Chicago’s O’hare (ORD).

    What do I need to bring to the event?

    • You must bring your own bike. If you want to arrange a bike rental, get in touch with us or snag one here. We know a guy.

    • You also need to bring your own camping equipment; we recommend you pack light. We also offer outfitting services if you fancy.

    • A tent or hammock and anything else you need to camp with would be useful too. Don't bring more than you can carry on a bike.

    • 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.

  • What about food?

    • 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.

  • Bike you say?

    • Hybrids work well because things get a bit unpredictable out there. Road bikes are fine but we’d prefer you take on the Drifty with Jerry, our tandem. Anybody doing it on a unicycle gets in for free.

  • Where will I sleep?

    • Sand bar, corn field, Motel 6... It's your call.

    • Camping is available along the entire route. Camping on the islands of the Wisconsin River is free and doesn‘t require a permit. Wyalusing State Park and Governor Dodge State Park are good spots to pitch a tent when you're back on dry land.

    • If you're looking for something more posh, we recommend a night at The Don Q Inn or Honkers.

  • Do I have to bring my printed ticket to the event?

    • We don't care. It will make for a good fire starter, so maybe bring it?

  • I’ve got a whole crew, what can you do for me?

    • Sounds like a party. We’ve been known to do discounts for groups that sign up together. Send us a note!

  • Are there ID or minimum age requirements to enter the event?

    • You must be at least 18 years old to take part in the event.

  • What's the refund policy?

    • Don't ask for a refund. You'll regret not doing The Drifty. But if you have to cancel, send us a note at least 30 days before the event and we'll let you off the hook.

  • How can I contact the organizer with any questions?

  • Is there anything else I need to know about the event?

    • There will be a surprise or two. That's all we can say.

  • I am a veteran of a Driftless 250, do I get any special treatments? 

    • Yes, veterans of the Drifty get a healthy discount and Pioneers get in fo’ FREE. On the back of your finish line medallion there's a code engraved. Type that in at checkout. ;)