FTC disclosure tour-de-force here. Updated Nov 20, 2025, this article contains one or more maps ...
Libertyville To Waterford: Roll Your Own Twisties
Moving our base of operations from Chicago's inner city to the "peaceful" northwest 'burbs didn't necessarily eliminate our difficulty in finding decent local motorcycle routes. Fortunately, Sheridan Road remains close but that can be a bit slow when sightseers are cruising the neighborhood mansions, which is why we sought out to map Libertyville to Waterford as a quick escape. To my surprise, a number of industry acquaintances live nearby and one of them, namely Tony Prust of Analog Motorcycles, was kind enough to send me a favorite of his maps.
“Libertyville to Waterford leads the way, a motorcycle route tested and tweaked for riders, its original line stretched to add more twisties.”
Having tested this route on my own and knowing what our readers (sport touring motorcycle enthusiasts) prefer, I've taken a few liberties in expanding Tony's original path. My efforts aim to keep things as twisty as limited roads will allow and the result is our new go-to day trip, a complete loop which heads due north into southern Wisconsin before returning southeast. Every section is individual, i.e. non-repeated and there are plenty of worthwhile stopping points along the way.
At first glance, you might think Libertyville to Waterford to be a boring, painted-lines, two-lane run with congested traffic and frequent stoplights. While it certainly isn't the driftless region, there's plenty of fun to be had. For the responsible motorcyclist, it's a solid riding route that uncovers curves in unexpected places, camouflaged by their public surroundings.
Leg One: Bristol, Wisconsin
For the first quarter of our ride, we're simply heading north in a beeline effort to escape Illinois. An isolated location, St. Raphael the Archangel Catholic Church marks the boundary between suburbia and small town mindsets. This building has an intimidating effect and used to be quite spooky. The story goes that funding for the church was gone before it could be finished, leaving a giant hollow structure standing deep away from the road in the middle of nowhere. Imagine seeing this along your commute every day, leaves off the trees, in the gray of winter.
Soon after, straight ahead or not, the Libertyville To Waterford scenery begins to develop a more relaxed and rural atmosphere. Telltale signs of our getaway's actual start come in the form of The Red School Cafe, an out-of-the-way favorite for breakfast and brunch. They aren't open on Mondays and close early otherwise, so be sure to get there early to avoid the lines!
Still rolling curvelessly forward, the occasional fruit stand makes for good "date" riding (two-up). Farmers markets and petting zoos pepper the area as well. If entering Vaj's Garage Restaurant & Filling Station doesn't trigger your passenger to call a cab home, consider 'em a keeper!
Leg Two: Waterford, Wisconsin
The next section banks a hard left out of Bristol, heading due west through the Conservation Club of Kenosha County on our Libertyville to Waterford loop. Here's where we find our first opportune curves. Things eventually straighten out for a moment (as they often will) until we reach the beautiful Silver Lake. Fox River Road then shows us some fun before ending at Route 83. No matter, though, because a right and then an immediate left put us back in better riding.
Serene flatlands with rolling borders are accented by horse pastures and grain fields. For the moment, motorists are few and far between. Riders have plenty of room to breathe here.
From here until Burlington, there are plenty of privacy and curves for cornering. A quick leap across the river and we point north once more, connecting to the Leda, Long and Brock lakefronts. This eventually bounces us from east back west via Rochester, a picker's oasis of sorts.
County Road D, with a detour along the twisty Ridge Lane, provides access to Honey Creek Road. Honey Creek then rendezvouses with Hill Valley, where we begin heading south. Throughout this subsection, we're met with well-paved sweepers, leafy canopies and one top-shelf perspective.
Before starting the trip home, Waterford affords a stop at Uncle Harry's Frozen Custard for a root beer float. All of the dairy being from surrounding farms, this place is no joke. We're talkin' over fifty flavors of ice cream, frozen custard and frozen yogurt!
Leg Three: Bristol Revisited
Our third quarter is similar to its predecessor in that its twisties are sought out aimlessly. A couple of nice jaunts point us past the Dover Inn (good sandwiches). Roundabouts help alleviate the straightaways. Then it's County Road A to scenic Sunnyside Drive where a series of unnecessary redirections are in order for the sake of grins. I even point us into a housing development (almost devoid of tenants) for a couple of good swerves and one looong left-handed sweeper.
Another straight and we're back in Burlington, sort of. Bong Recreation Area and the surrounding forests soon provide another pleasantly secluded environment. The more interesting, albeit entry-level, curves continue until things flatten out where County Road K and County Road D intersect.
Leg Four: Libertyville, Illinois
By now, you can probably guess that our Libertyville to Waterford ride is beginning to mellow. The scenery, on the other hand, continues to ease the soul. Farmland and small cottages dot our way to Old Mill Creek with the occasional roundabout to keep things interesting.
A sweep to the left and another right put us in Gurnee Mills before a brief pause for mall folk. Nonsensically turning right onto Dada Drive, we slow things down for a few remaining curves. That final turn onto Milwaukee Avenue puts the four o'clock sun on our right, in the valley, setting quietly behind the tree line.
To conclude things, our new favorite local motorcycle route proves that, with a little effort, you can develop nearby riding that's at least entertaining. Be mindful not only of the authorities but the people who live there as well. Respect their communities. Keep alert and stay safe. Even at low speeds in "less than interesting" areas, good times can be had on your motorbike.
What Local Motorcycle Routes Have You Conjured?
It's hard to find decent riding roads when you live on a flat grid. What maps have you come up with? What do you like about them and why? Your input is invited. Leave a comment and/or write an article!
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About Robin Dean
Motorcycle advocate, enthusiast and traveler. Founder, The Riding Obsession (2014). MSF RiderCoach credentials: "loosely regarded adult supervisor, probably good enough for rock 'n' roll" ~ Tidal Playlist | Rabid Neon
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