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Mar 5th: 2022 Driftless Challenge!!

Driftless Challenge:

We are excited to announce the 2022 Driftless Challenge 2.0 is starting April 1st!

Want to ride some new roads, see some new and interesting sights, and maybe win some prizes? Then the Driftless Challenge is for you.

Here is 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. Enjoy some of our entries from last year:

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. Here is a list of previous winners:

​​​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!

New Routes:

As you may know, we are working hard on adding new routes and working with our test riders to get them verified. We are currently working on routes in the Ozarks, Arizona, Colorado, and the Great River Road.

If you are looking for a route in a certain area, let us know. We might be able to move some planned routes higher on the priority list.

Don't forget that we also create custom routes for riders that want a special one-of-a-kind ride. Drop us a note with any questions and we can set up a time to discuss exactly what you are looking for.

Have a great weekend!

Ride Safe

Dale and Renee

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