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Nov 5th Update – Driftless Challenge Grand Prize Winner!!

One Last Ride?  Probably Not 🙁

If you read last weeks post, you know that we have been tied up at home with our puppy’s recovery.  This weekend is still a no-go because although her stitches are out, she is still healing.

Even though we can’t take a big riding trip, I’m hoping it will warm up enough to take a few day trips locally yet this year.


Here is a gratuitous shot of my bike in warmer times!!

Changes on the way:

As we mentioned last week, we have begun to make some changes to many aspects of Driftless Road Adventures.  We are doing our best to test changes as we go, but we need your help too!  If you notice a problem or a broken link, please take the time to let us know so we can fix it ASAP.



Also, if you have any ideas for changes you would like to see, new routes or roads,  recommendations for the Driftless Challenge or something else you would like to see on our website, send us a note.  We would love to hear from you and will consider all suggestions carefully.


Driftless Challenge – October:

The October Driftless Challenge is over and the winner was once again Nat P.!  Thanks Nat for all the great pictures you shared with us this year!  Nat’s final entry was a picture at the Rock in the House which is located in Fountain City, WI, and is exactly what it sounds like…a rock in a house.  Here is Nat’s picture as well as one of our own:

Rock in House.jpg


Driftless Challenge – Grand Prize Winner:

Our 2019 Driftless Challenge is over and we want to thank everyone that entered and congratulate all of the monthly winners.

Each of the monthly winners was entered into our Grand Prize drawing as well.  We are excited to announce that the 2019 Driftless Challenge Grand Prize Winner is Doug M. (below).  Thank you Doug for sharing all of your wonderful pictures with us.


Remember that you can view all of the Driftless Challenge entry photos here.

When we created the Driftless Challenge, we wanted to find a way to get people to explore the Driftless Area, and based on the results and the feedback we received, we think it was a success!

We are looking forward to the 2020 Driftless Challenge and have begun to scout out new challenge locations.  Look for the 2020 Driftless Challenge rules and locations in the spring!

Upcoming Driftless Events:

Jan 31st/Feb 2nd 2020:  Progressive Motorcycle Show – Minneapolis, MN

Feb 7th/9th 2020:  Progressive Motorcycle Show – Chicago, IL


  • Planning for next years rides?  Our paper maps make great planning tools!
  • Need help planning a trip?  Driftless Road Adventures can custom design a route anywhere you want, just send us an email and let’s talk.
  • Shopping for a friend who rides?  Our paper maps and pre-loaded SD cards make great gifts.
  • Please visit our Driftless Store.   Remember, all sales go directly to website maintenance and improvements.


Hope you are having a great week!  Ride Safe!

Dale and Renee

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