Most Dangerous Motorcycle Rides in Wisconsin
The Most Dangerous Motorcycle Rides in Wisconsin
Beautiful Roads. Real Risks. Here’s What Every Rider Should Know.
Let’s be honest—Wisconsin is made for motorcycles. The winding backroads, rolling farmland, scenic lakefronts, and crisp summer air all combine to create some of the best riding in the Midwest.
We love this state. We’ve ridden these roads ourselves. We know the thrill of a good curve and the peace of cruising down a two-lane highway with nothing but time and the open road ahead.
But we also know that not every ride is created equal.
Some routes in Wisconsin—while undeniably beautiful—come with real risks. Sharp turns. Blind hills. Distracted drivers. Deer around every corner. Crumbling pavement. Weekend warriors in oversized pickups who don’t respect riders.
At McCarthy Motorcycle Law, we believe in all the gear, all the time, and we believe that knowledge is power. This page is here to give you a straight-up breakdown of Wisconsin’s most dangerous motorcycle rides—where the beauty is high, but so is the risk.
We’re not trying to scare you off the road. We’re just here to make sure you stay sharp, ride smart, and make it home safe.
1. The Driftless Area – Highway 33 from Baraboo to La Crosse
If you’ve ever ridden the Driftless Region, you already know: this is some of the best riding in the Midwest. Curves. Hills. Ancient geology. Small towns. It’s a motorcyclist’s dream.
But Highway 33? It’s no joke.
This twisting, turning ribbon of blacktop cuts through steep valleys and bluffs, with more than a few decreasing-radius curves that’ll catch you off guard if you’re not paying attention. On a nice day, it’s packed with cars, bikes, and RVs. On a wet day, it’s slick as hell.
Why it’s dangerous:
Sharp, blind corners
Inconsistent pavement
High-speed traffic in rural areas
Risk of overconfidence on a scenic ride
Ride it safe:
Stay within your skill level—don’t push your limits just because the view is nice
Watch for farm vehicles and gravel patches, especially near town edges
Slow down before the corners, not in them
2. Highway 42 – Door County’s Iconic Curves
This one’s on every “Best Rides in Wisconsin” list—and for good reason. The stretch of Highway 42 near the tip of Door County is legendary, with its winding switchbacks that snake through thick forests and pop out along the water.
It’s beautiful. It’s thrilling. And it’s also one of the most accident-prone roads in the state during peak season.
Why it’s dangerous:
Heavy tourist traffic from May through October
Narrow lanes with little room for error
Drivers who are unfamiliar with the road—or distracted by the scenery
Sudden deer crossings (especially at dusk)
Ride it safe:
Go early in the day to avoid traffic
Assume drivers don’t see you—especially when they’re pulling out from parks or orchards
Take your time; it’s not a race
3. I-94 Corridor – Milwaukee to Madison
This isn’t a scenic ride—it’s a necessary evil for many riders traveling between the state’s two biggest cities. But make no mistake: riding I-94 on two wheels is a gamble.
High speeds. Aggressive drivers. Constant lane changes. And way too many people looking at their phones instead of the road.
Why it’s dangerous:
High volume of semi-trucks and tailgating drivers
Little to no shoulder in some areas
Debris in the roadway
Zero tolerance for error at 75+ mph
Ride it safe:
If you must ride the interstate, ride alert and defensive
Avoid riding in blind spots—especially next to trucks
Give yourself an exit route in every lane
Wear high-viz gear, even in daylight
4. County Road A – Walworth County Backroads
Walworth County is full of amazing little routes that wind through farmland, woods, and lakes. But County Road A has developed a reputation—especially on weekends.
This route is popular with both local riders and suburban tourists out for a “country cruise.” But it’s also narrow, hilly, and unpredictable. Think patchy pavement, loose gravel, and drivers who really don’t expect to see a bike coming.
Why it’s dangerous:
Uneven road surfaces
Blind driveways and tractor entrances
Drunk driving incidents (especially near Lake Geneva on weekends)
Ride it safe:
Keep a wide field of vision
Be careful around turns with shaded pavement—gravel tends to collect there
Avoid riding late at night, especially Friday and Saturday
5. Devil’s Lake to Prairie du Sac – Highway 78
This stretch between Devil’s Lake State Park and Prairie du Sac hugs the river and feels like something out of a motorcycle ad. The scenery is stunning, especially in the fall.
But beauty comes with risk.
This two-lane road has tight curves, lots of elevation change, and plenty of distracted drivers checking out the view. Add in tourist traffic and wildlife crossings, and it can go from smooth cruise to “oh, sh*t” in seconds.
Why it’s dangerous:
Sharp curves with limited sight distance
Inconsistent shoulder width
Cars crossing the centerline while gawking at eagles or river bluffs
Big groups of riders, often at mixed skill levels
Ride it safe:
Ride staggered and leave extra space if you’re in a group
Keep your head on a swivel—especially in areas with heavy foliage
Use your horn if a car starts drifting
6. Highway 35 – The Great River Road
We saved this one for last because, well—it’s a classic.
The Great River Road runs alongside the Mississippi River and is widely considered one of the most scenic motorcycle rides in Wisconsin. From Prescott to Prairie du Chien, it’s miles of curves, views, river towns, and good food stops.
But don’t let the beauty distract you. Riders crash here all the time.
Why it’s dangerous:
Narrow lanes in older river towns
Heavy bar traffic on weekends
Deer, sand, and broken pavement in river curves
Drivers unfamiliar with the area—and not paying attention
Ride it safe:
Take extra care around town entrances and exits
Stop for breaks; don’t ride tired, especially with the river glare
Bring your best gear—it’s a long haul if something goes wrong
Let’s Talk About Safety
We’ll be the first to say it: you don’t ride because it’s safe. You ride because you love it. Because it clears your head. Because it reminds you that you’re alive.
And we’re not here to lecture. But we do care. And we’ve seen way too many good riders go down because of things they couldn’t control.
That’s why we always say:
All the gear. All the time.
Helmet. Gloves. Jacket. Boots. Eye protection. Even for a short ride. Even if you’re “just going to the store.” Because the truth is, you don’t get to pick the moment something goes wrong.
The gear might save your life. It might make the difference between a fractured rib and a funeral. And if you ever need to bring an injury claim, being geared up shows that you were taking your safety seriously—something insurance companies and juries pay attention to.
If You’ve Been Hurt on One of These Roads, You’re Not Alone
We hope every ride ends with a cold drink and a smile. But we also know that crashes happen—even to the best riders, on the best roads, in broad daylight.
If you’ve been hit or injured on one of these Wisconsin routes—or anywhere in the state—we’re here to help.
At McCarthy Motorcycle Law, we’re not just lawyers. We’re rider advocates. And we’ve helped injured motorcyclists across Wisconsin get the medical care, support, and compensation they need to get their lives back.
We know what it’s like to be judged for riding. We know what it’s like when the insurance company tries to pin the blame on you just for being on a bike. And we know how to fight back.
Free Case Evaluations for Injured Riders
If you or a loved one has been hurt in a crash:
We’ll review your case for free
We’ll tell you the truth about your options
And we won’t charge a dime unless we win
You don’t have to go it alone. Whether the crash happened on Highway 35, County A, or some backroad nobody’s ever heard of—we’re here. Get started today with your free case review.
McCarthy Motorcycle Law
For Wisconsin Riders. On Every Road. Every Mile. Every Case.
Free Case Evaluation | No Pressure | Just Real Help