The Drifty

An 8-Day 250-Mile Kayak & Bike Challenge Starting In Madison, Wisconsin, and Covering the Driftless Region.

hAPPENING ON

Aug 2

-

Aug 10, 2025

PRICE STARTS AT
$575
REGISTER
overview

A Ride Through the Wild Side of Wisconsin

This isn’t some neatly packaged, influencer-approved itinerary. The Drifty is eight days of sweat, grit, and borderline poor decision-making through Wisconsin’s Driftless Region—an outlaw’s paradise of rugged hills, winding rivers, and roads that seem to exist purely to punish your legs.

You’ll bike through landscapes most tourists never see, paddle down rivers that feel untouched, and sleep under stars so clear they’ll make you question why you ever paid for a hotel. Sandbar camping? Check. Encounters with oddball locals at backwoods bars? Absolutely. The kind of stories that start with, “You’re never going to believe this, but…”—yeah, you’ll have plenty of those.

And just when you think you’re too beat to go on, we cap it all off with Drifty-Fest—a finish-line party where the beer flows like the Wisconsin River and the legends of the week get properly exaggerated.

  • Total Miles: 250ish (give or take a wrong turn)
  • Transport: Bikes, kayaks, canoes, and sheer willpower
  • Lodging: Camping under the sky or whatever hotel bed you’re lucky enough to find

It’s not a race. It’s not a tour. It’s an adventure. And it sure as hell isn’t for everyone. But if you get it, you get it.

register
What Makes It Great

Safe-ish

While it’s very unlikely you’ll die, there is always the off chance that you flip your canoe, run your bike into a cow, or get attacked by an eagle. We won’t be holding your hand, but we will do our best to keep you out of the hospital.

Unconventional

While our event does require physical activity we are more about the fun than the run. Wear a chicken suit? Encouraged. Hit every dive bar along the way? It’s a strategy. Your goal is to have fun & make it to the finish line.

Camaraderie

Nothing bonds total strangers like a shared struggle and positive attitudes. Our events bring together unique outgoing folks from all over the world with a passion for unscripted fun.

Drifty-Fest

We want you to finish with a bang. That’s why we host the Drifty Fest. An epic party with live music, great food, local brews & hilarious awards. This is an event you can invite your friends and family as well!

THE ROUTE

the Loose route

The Drifty isn't about following some pre-planned, boring route.  We'll get you started, point you in the general direction of awesome, and then... you're on your own (mostly).. We'll handle the logistics – bikes, boats, the occasional 'don't die' pep talk – but the rest is up to you.  Feel like paddling down that sketchy-looking creek?  Sure, why not?  Think that abandoned logging road looks like a shortcut?  Knock yourself out!

THE RATES

pricing

What’s included?

Can you put a price on lifelong memories and friendships?  Probably not, but we can put a price on the Lil' Drifty, and it's a steal!  You get: entry into the adventure, your trusty kayak or canoe, bike transport at the transition points, luggage storage, some sweet swag to show off your Drifty cred, a shiny medal because you're awesome, some other surprises and food & drinks at the epic finish line party a.k.a. DRIFTY FEST.

(1) PERSON
(1) KAYAK
INDIVIDUAL
FOR ONLY
$ 300
register
(2) PEOPLE
(1) CANOE
TEAM OF 2
SAVE $50!
FOR ONLY
$ 550
register
(3) PEOPLE
(1) CANOE
TEAM OF 3
SAVE $150!
FOR ONLY
$ 750
register

NOT YET READY TO BOOK?

LOCK IN YOUR SPOT
FOR ONLY
$ 50
reserve
What’s included?

Can you put a price on lifelong memories and friendships? Probably not, but we can put a price on the Lil' Drifty, and it's a steal!  You get: entry into the adventure, your trusty kayak or canoe, bike transport at the transition points, luggage storage, some sweet swag to show off your Drifty cred, a shiny medal because you're awesome, some other surprises and food & drinks at the epic finish line party a.k.a. DRIFTY FEST.

(1) PERSON
(1) KAYAK
INDIVIDUAL
FOR ONLY
$ 575
register
(2) PEOPLE
(1) CANOE
TEAM OF 2
FOR ONLY
$ 999
register
What’s included?
price: $1900

Can you put a price on lifelong memories and friendships? Probably not, but we can put a price on the Lil' Drifty, and it's a steal!  You get: entry into the adventure, your trusty kayak or canoe, bike transport at the transition points, luggage storage, some sweet swag to show off your Drifty cred, a shiny medal because you're awesome, some other surprises and food & drinks at the epic finish line party a.k.a. DRIFTY FEST.

PRE-REGISTRATION
FOR ONLY
$ 50
register
(1) PERSON
(1) KAYAK
INDIVIDUAL
FOR ONLY
$ 575
register
(2) PEOPLE
(1) CANOE
TEAM OF 2
FOR ONLY
$ 999
register
PRE-REGISTRATION
FOR ONLY
$ 50
register
What’s included?

Can you put a price on lifelong memories and friendships? Probably not, but we can put a price on the Lil' Drifty, and it's a steal!  You get: entry into the adventure, your trusty kayak or canoe, bike transport at the transition points, luggage storage, some sweet swag to show off your Drifty cred, a shiny medal because you're awesome, some other surprises and food & drinks at the epic finish line party a.k.a. DRIFTY FEST.

PRE-REGISTRATION
FOR ONLY
$ 50
register
(1) PERSON
(1) KAYAK
INDIVIDUAL
FOR ONLY
$ 575
register
(2) PEOPLE
(1) CANOE
TEAM OF 2
FOR ONLY
$ 999
register
PRE-REGISTRATION
FOR ONLY
$ 50
register
Could not ask for better people to get lost with. The staff is first class to answer questions and help when situations arise. You will not regret doing any trip with this company.

Beth Walker

,

Could not ask for better people to get lost with. The staff is first class to answer questions and help when situations arise. You will not regret doing any trip with this company.

Beth Walker

,

It is a week to completely unplug and to be in nature while testing how “outdoorsy” you really are. It is the perfect trip if you’re ready to do something a little more intense than tent camping at a camp site but are not ready to commit fully to Bear Grylls.

Blake Miller

,

I did the Drifty back in 2021. Wouldn't trade the experience for anything! My favorite quote came from a 60-something year old gentleman named Don. At the closing party he said, "I'd rather wear out than rust out." He's a certified badass.

Derek Riechers

,

We had a blast while Lost in Sicily. We met new friends and made memories to last a lifetime. The trip was perfectly organized to allow for tons of exploring and adventure along with a fabulous guide to manage those of us a little more “type A”. Lost Travel Co.is amazing and Keegan took great care of us while Jake checked in for added support. Highly recommend traveling with this group for a great adventure!!

Julie Creaden

,

what to expect

general itinerary

faqs

infrequently asked questions

Find answers to common questions about our events.
What do I need to pack?

Two panniers are standard and should be sufficient. Bring a slingshot and a pair of fresh underwear, just in case. We'd recommend a tent since that's the most versatile, but hammocks are doable if you want to pack light. Make sure to bring all of your own biking safety gear: helmet, gloves, etc. The kayak/canoe rental comes with life vests, paddles, etc.

On land, you'll have access to bathrooms wherever you go. When you're on the river, the only option is to dig a hole and poop in it, so we recommend bringing a cat trowel. Also, bring a spare tube for your bike tire along with anything you'd need for bike maintenance. We'll have a mobile bike shop at the kickoff, but once you leave the start line, everything is on you, Drifty style.

What meals do I need to plan for?

Kickoff night and finish line meals are on us! In between, you’re on your own. There are ample grocery stores and restaurants along the biking route (no matter which way you go!) so we don't think you need to bring a ton of food to start. Many people will stop at the grocery store before getting on the canoes. This is a good time to stock up on water, drinks, food, etc. At the transition to canoes we'll have some fire wood you can take with you so you can have a camp fire.

What do I do with my car for the duration of the event?

Our best advice is to not bring a car with you. The best car is no car. Ideally, get yourself dropped off at the kickoff camp and have someone meet you at Drifty Fest. We'll even toss them a free beer. If that's not possible, there is paid, secure parking at the Dane County airport. The covered ramp costs $10/day, the surface lot is $8/day, and the economy lot is $6/day. Pro tip: The finish line is only 2 miles from the airport. Alternatively, there's free surface parking at the Dutch Mill Park & Ride, which is 10 miles to the start line and 6.5 miles to the finish line.

Do you have any tips?

Wave at everybody—it's a Wisconsin thing. Avoid Highway 18. Try Spotted Cow—if you haven’t done it, do it. Tie your canoe to something. It's an adventure, get drifty with it.

Are there any rules?

No camping on the shoreline unless you're in a campground. Islands and sandbars are okay! No glass containers. No fireworks. Fun—have it.

What if I sign up alone?

No worries. Your future best friends already signed up for this trip. Our kickoff festivities are all about building camaraderie so you won’t have to ride solo.

Do I need a bike or a kayak/canoe?

A kayak and canoe are included in your registration. We recommend bringing your own bike. However if this isn’t an option, we will set you up with rental options.

exit icon

join the waitlist

Sign up and be updated on the latest news about this event.