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The Driftless 250 - Spring Edition

Lost Travel Company

Saturday, May 11, 2019 at 7:00 PM - Saturday, May 18, 2019 at 10:00 PM (CDT)

The Driftless 250 - Spring Edition

Registration Information

Registration Type Sales End Price Fee Quantity
Ticket for 1 Adventurous Soul May 1, 2019 $225.00 $15.33
Donation to River Alliance of Wisconsin (Optional)   more info May 11, 2019 Enter donation ($)
Outfitting for 1 Adventurer (Optional)   more info May 11, 2019 $150.00 $10.76

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Event Details

Ticket Prices

$199 until January 1st, 2019

$225 until March 1st, 2019

$245 until May 1st, 2019


250 miles. 7 days. Bike -> Paddle -> Bike. 

The Driftless 250 is an 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.


--- DATES --- 

MAY 11TH - MAY 18TH, 2019

Kickoff Party - Sat, May 11th - Downtown Madison, WI

Start Line - Sun, May 12th - ???

Finish Line and Party - Say, May 18th - Middleton, WI


--- ENTRY FEE ---

What do you get for your money?

  • 7 days of beautifully unscripted travel
  • A mostly sea-worthy canoe
  • Paddles and life vests for your whole team
  • At least one bald eagle sighting (We stopped counting at 20)
  • A week's worth of RX Bars and nut butters ($25 value)
  • A week's worth of AlpineAire backpacking meals and Snacks ($100 value).
  • Transportation and secure storage for your bike while you're drifting down the river
  • 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

--- THE (UN)ROUTE ---

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?"

The Driftless 250 will start somewhere near 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 GPS coordinates engraved on it.

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 4-5 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 days; more if you paddled fast, less if you paddle slow. (~125 miles)

The finish line is also 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.


--- TEAM ---

This event can be done as an individual but we recommend doing it as a team. 2 people is probably ideal but it would be more fun if you cram 3 people into a canoe.

--- DATES --- 

Sat, May 11th - Afternoon Check-in and Launch party in the evening

Sun, May 12th - Event kicks off bright and early in the morning, no matter how hungover you are. Don't forget to call your Mom. 

May 12th to May 18th - Biking, paddling, camping, getting lost, arguing with your teammates, running out of booze on day 2, etc.

Sat, May 18th - Finish line is open all day followed by a Finish line party at night.


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. Additional questions? Ask a Pioneer at

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

--- FAQs ---

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 GPS coordinates of the start line carved into it. You'll receive this about a month before the event starts. Plan on being within 15 miles of Madison, WI, USA on May 11th.

If you're flying in, book tickets to/from MSN (Dane County Regional Airport).

What do I need to bring to the event?

You must bring your own bike. You also need to bring your own camping equipment; we recommend you pack light.

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. 

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.

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?

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, 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?

Scroll down and click "Contact" to send us a message.

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 Pioneer of the original Driftless 250, do I get any special treatments? 

Yes, Pioneers of the original Drifty get in for FREE. On the back of your finish line medallion there's a code engraved. Type that in for free entry. ;)

Have questions about The Driftless 250 - Spring Edition? Contact Lost Travel Company

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When & Where

The Driftless Region
2 East Main Street
Madison, WI 53703

Saturday, May 11, 2019 at 7:00 PM - Saturday, May 18, 2019 at 10:00 PM (CDT)

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Lost Travel Company

We're a travel company that caters to the curious. Learn more about us and our 5% for the Planet program at 

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