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Driftless Challenge

Here's How It Works...

Driftless Challenge participants will choose the locations they wish to visit, from the list below, 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.  Each photo equals one entry in a monthly random drawing.

The contest will run April 1st through October 31st.  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?


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


So, gear up, grab your camera and hit the road. You will have a great time, and who knows, you could win some cool prizes!  

2022 Winners:

  • April:  Mark H.

  • May:  Greg T.

  • June:  Robin H.

  • July:  Mike E.

  • August:  Mike E.

  • September:  Gary P.

  • October:  Kim L.

  • 2022 Grand Prize:  Mike E.

Would you like a download of all of the 2023 sites?  Just click here to get a free download!

2023 Sites

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