Welcome to RollingDriftless: Your Guide to the Midwest’s Best Kept Riding Secrets. 🏍️🌲
If you believe that the best roads aren’t on the map and the best meals aren't found in a franchise, you’re in the right place.
I’m on a mission to document the Driftless Region on my Harley Roadglide. The Driftless region is a rugged, un-glaciated corner of the Midwest full of twisting backroads, massive river bluffs, and quaint small-towns. From the switchbacks of Wildcat Mountain and the Mindoro Cut to classic biker stops like Bucknuckles, The Lookout, and Rockton Bar, we’re carving out the best routes so you know exactly where to twist the throttle and stop on your next ride.
On this channel, you’ll find:
- Stunning overlooks and biker friendly lunch stops with great food
- An "Alphabet soup" of roads carving through the valleys and bluffs
- Harley-Davidson Adventure: Trip videos from our motorcycle adventures around the country
Rolling Driftless
Stay tuned for some different types of content in the next few weeks as we wait for the snow to melt and riding season to get rolling.
This coming week, you will see a video about how I do trip planning using a combination of Google MyMaps and Rever. Hope you find that useful.
The following week, we release a video called "Decoding the Driftless". We describe what the Driftless Region is and how it came to be. The video also includes ride video from some of the best roads and overlooks in the State. Look forward to hearing your comments on this one!
2 weeks ago | [YT] | 4
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Rolling Driftless
Here's a link to a bunch of Rolling Driftless Rides on Rever for anyone interested.
go.rever.co/bmRDCnAj2Zb
4 weeks ago | [YT] | 2
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Rolling Driftless
Headline: Who’s ready to do some riding in the Driftless Region?
🏍️
The 2026 Great Lakes H.O.G. Rally is officially coming to our backyard June 11–13th, 2026. We hosted this rally in 2024 and are bringing it back by popular demand.
Follow this group on FB for information about the rally, how to register, hotel information, and weekly ride teasers.
facebook.com/GreatLakesHogRally
We are finalizing the routes now and I’ll be leading rides daily as will other members of the Indianhead H.O.G. Chapter. Come join us as we would love to take you on some of our favorite routes!
1 month ago | [YT] | 4
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Rolling Driftless
Hi everyone, welcome to my new YouTube Community! Now you can post on my channel, too. To get started, let me know what you would like to see more of in my videos in 2026.
Visit my Community: youtube.com/@RollingDriftless/community
1 month ago | [YT] | 0
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