Recommended rides

I have a lot of people ask me for the links to routes I have created. Some of the routes were used in events, and some have just gathered a following for being the best the particular area has to offer. I wanted to make a place to catalog a few of the routes most worth sharing, full of the roads I regularly traverse. All of these are in Northern Illinois, as that is where I’ve explored the first 30 years of my life, and the only area I consider myself a knowledgeable authority on.

Silver Springs 106k
I’ll start with the ride closest to my childhood backyard, as I grew up 2 miles away, and served on the fire department that covered this area for 5 years.
I have memories of Silver Springs going back far as any, and as I got older it would continue to be a special place of escape for me.
Lots of people from the city and suburbs have come out to ride this route now, and for many it has become a nearly monthly trip for them. I am glad people seem to enjoy it.
This is probably 25% gravel, wear the appropriate tires.


Rock River 95k
Where I’ve spent the most recent five years of my life is really flat, and rather mundane. When I need to escape but don’t have all day, I go to the Rock River valley.
The rock river valley has a lot to explore. There are Bison, rock outcroppings, natural artesian springs to fill bottles at, and the major reason I drive out from Dekalb, it features hills and trees. Roads are mixed pavement and gravel.
The above route is my go to when I venture out there, but for even more options, locals have created a page with a plethora of options to see even more of what is waiting for you at Discover Oregon Illinois.


Ten Thousand 1st edition
Ten Thousand was something that came out of a serious infatuation with the Driftless region a few years ago. I could not, and still can’t, get enough riding out there. Quite simply it is the best riding in Illinois, and is world class. This route was designed when I was involved with a shop in the town of Freeport, so I started the route in that locale.
This is the easier of the two editions, simply because Freeport is a bit outside of the hilliest area, and you get a bit of a warm up and cool down. Still a difficult day on the bicycle. Mixed pavement and gravel.


Bailey’s point of view

Ten Thousand 2nd edition
This was the third route I made in the Driftless, after the 1st edition, and the course and logistics for the Rapha Midwest Prestige. Changing the starting location opened up many new roads, and allowed me to increase the difficulty, which no one particularly asked for.
My major design goal for this route was to take riders through a changing experience, where the road personality took on different characteristics as the ride progressed. I couldn’t be happier with the final result.

Illinois Will End You
Something I have always wondered is how would a 200 mile ride in the Driftless compare to the Dirty kanza? I still have solidly not answered that question, yet. The only thing I am certain of, is that it will be substantially harder.
I keep changing my mind on which direction I want to ride this route. Both have their intriguing aspects. I put this up here as the biggest carrot on a stick Illinois has to offer, the holy grail, of sorts. If you think about doing this, let me know, and I can provide all of my knowledge with you. If you finish, I’ll give you a hug and buy you a beer next time I see you.

More to come in time. Stay in touch. Talk to me >here<.