Driftless Challenge 2018

Driftless Road Adventures is proud to present the 2018 Driftless Challenge!

The Driftless Challenge is a non-timed road rally that requires travel throughout the entire Driftless Area at your pace, on your schedule.  There are three levels of achievement.

  • Gold:  Ride ALL 33 of our routes…yup, that’s 7,500 miles in a single season.
  • Silver:  Ride at least 22 of our 33 routes in a single season.
  • Bronze:  Ride at least 11 of our routes in a single season.

The season for this challenge runs March 1st through October 31st.

Along each of the 33 routes there are 3 specific locations which must be visited and photographed.  Some of these locations may be businesses, but no purchase is ever required.

So how does it work?

  • Enter with the form below
  • Pay your entry fee of $25.00 per person ($50.00 for 2 up) by using the Paypal donation button.  Entries are accepted at any time…you do not have to start March 1st.
  • You will receive  a reply from us with the following:
    • A file so you can print a placard with your number on it.  (We recommend you laminate it since it has to be with you for the whole journey)
    • A file with all of the specific points of interest that you must stop and photograph.
  • Included in each photo submitted must be:
    • The specific site or item…this could be a building, a sign, an actual item or natural phenomenon…just something that tells us you were there.
    • Your placard
    • Your motorcycle NOTE:  If you can’t get your motorcycle close enough to the item, take a close up picture of the item AND a picture farther away that does include your bike.

What you will receive if you conquer the challenge:

  • Hours of enjoyment from riding the greatest roads in the Driftless Area.
  • A sense of accomplishment for achieving something that few others have done.
  • Your name on the Driftless Challenge Finishers list.
  • A Driftless Challenge T-shirt to show off to all of your riding buddies.
  • A Driftless Road Adventures sticker.
  • A certificate of completion.


  • First and foremost, BE SAFE, don’t stand in traffic to get a picture!
  • Photos can be emailed, or can be shared through a digital photo gallery.
  • All questions and final photo submissions should be emailed to driftlessroadadventures@gmail.com
  • Photos must be submitted no later than October 31st, 2018.


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