Driftless Challenge 2021

The Driftless Challenge is starting a month early for 2021!  This year we have a list of 66 locations located on our routes in the Driftless Area. We have added a twist for 2021!  Any sign with the word "Driftless" in it can also be used as an entry!


Driftless Challenge participants will choose the locations they wish to visit and take a photo with both their motorcycle and the location in the shot (safety first, don’t walk into traffic for a photo). Participants will then submit their photos to us.

The contest will run April 1st through October 31st, with one lucky participant winning the random drawing each month. Every picture a rider sends us equals one entry into that month’s drawing.

Riders can enter as many pictures that they want in any given month. The more pictures, the better your chance of winning. However, if you want to enter the contest for more than one month, you must send in new pictures (no recycling).

As mentioned above, there will be a winner every month for 7 months. At the end of October we will have a drawing for the Grand Prize from among all of the monthly winners.

How much is it to enter? It’s Free! You can’t beat that price.

Where do I send the pictures? DriftlessRoadAdventures@gmail.com.

How will I know if I win? We will notify the winners by email. We will also post the winners on the site and on our Facebook page.

Other questions? Send us a note through the contact form, or send us an email at DriftlessRoadAdventures@gmail.com.

So, gear up, grab your camera and hit the Driftless Area. You will have a great time, and who knows, you could win some cool prizes!  See below for all of this years locations!!

For a download of the Specific Locations click here.

August 2021 Winner.png