Join our Team

We’re on a mission to make people happy and connect them on a deeper level with themselves, others, and the planet. We do this by getting them into unpredictable situations. Sound like your cup of joe? Come join us. We need a few more folks to help row this canoe.


Ambassadors help get the word out about our trips and make money doing it. If you get excited about energizing other people to do something crazy, this gig’s for you. Only the adventurous and creative need apply.

How it works: You will be working side-by-side with us to get people excited about The Driftless 250. We’ll hook you up with the physical and digital assets you need to be successful. We’ll also provide the fancy internet tools needed for you to track your work.

What you get for it: Lost Travel swag, Cash money for registrations, discounted entry to events, gratitude, and other neat perks.

Year Round

UnSupport Crew

You might be qualified to join our crew if any of the following sound like fun: scouring craigslist for a working tandem bike at least 20 years old, driving a trailer full of canoes on winding roads, frantically searching for a taco truck.

How it works: Help out with whatever nonsense comes your way.

What you get for it: Lost Travel swag, Food and your favorite tipple at the kickoff and finish parties, discounted entry to a future event, blood, sweat, tears, and so much more.

May 2020 - Driftless 250 - spring Edition

Sign up for any/all of the following dates: May 16 (Sa), 17 (Su), 20 (We), 13 (Sa).


Contact Us Below

Let us know how you’d like to get involved in the message body. We’ll follow-up real quick like.

Name *