Jason S. of Chicago tells Twisted Road about the well-known roads he's ridden and some surprising ones that just might make you head to the Midwest to rent a bike and explore them for yourself. 

How long have you been riding, which bikes have you owned and how did you become interested in riding?

I've been riding for over 20 years. I started on Dad's "borrowed" Harley. First bike of my own was a 1957 Vespa that was given to me; I restored it lovingly and eventually sold it to a well-known Indian collector who had always wanted one. Then I was on to a Sportster of my own, promptly torn down, metal flaked, and chopped the fenders.

I've always loved the freedom that riding provides. I started on Sportsters and Vespas, but when I discovered adventure riding, I was absolutely hooked. I've owned a half-dozen bikes since then, from cafe racers to my beloved Africa Twin. Since then I've been all over the country on my bike and plenty of others from Twisted Road.

What moto trips have you taken (long or short). Where did you go, stay and explore? Tell us some highlights.

I've done several trips out West. I have family in Las Vegas and my brother and I have headed off road to the Bonneville Salt Flats, ridden the Slickrock Trail in Moab, the North Rim of the Grand Canyon, Toquerville Falls, Death Valley and into the California Sierras.

Here in the Midwest, we've done the Trans Wisconsin Adventure Trail (TWAT) the Great River Gravel Ride (GRGR) and the Cheese County Trail in Wisconsin -- all highly recommended dirt rides. It's great to have friends that love adventure riding too.

What hobbies do you enjoy when you're not riding? 

Anything outdoors! I love camping with my family; we're on a quest to hike every waterfall in Illinois (there are surprisingly a ton of them!). I love boats all summer and we ski in the winter.

Tell us some more about you - where do you live? What kind of work do you do?

I live in the north suburbs of Chicago—which has a great motorcycle community but not a lot of great rides nearby—but the alphabet roads of Wisconsin are never far. For work, I run a healthcare company providing physician care to senior communities throughout the Midwest.

What do you enjoy about being part of the Twisted Road community?

I was a rider before I was an owner. I've found that the coolest people ride motorcycles. I've had the most fun random conversations in driveways about bikes, talking about the trips we are about to take or the best rides we've had. My bike has been out to run the Twisted Dragon and crossed the country a few times more on rentals. A few have taken it off-road on the trails and into the sand dunes.

Twisted Road Inside Scoop: Jason's bike has been rented by a few of our very own Twisted Road Staff (see below).

What are your favorite rides near your hometown?

Within a few hours, the best rides are the Trans-Wisconsin Adventure Trail, the Great River Gravel Ride, and the Cheese County Trail. Of course you can't beat taking a day to ride up Sheridan Road along Lake Michigan or cruising the rustic roads of Wisconsin.

What location is on your moto trip bucket list?

I'd love to do a trip in Baja, Mexico or an extended trip to Patagonia!

Check out Jason's Bike Available For Rent On Twisted Road:

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