There’s something special about riding in the Midwest, and Wisconsin delivers the full experience—rolling roads, wooded corridors, glistening lakes, and quirky roadside stops that feel straight out of a 1970s road movie. As a Gen-X rider who grew up on dirt bikes and now leans into three wheels for comfort and control, I can tell you: Wisconsin might be one of the most underrated states to explore by motorcycle or Can-Am Spyder. Whether you're looking for peaceful backroads, vibrant small-town culture, or a killer plate of cheese curds, this ride delivers.

This guide is designed for riders like us—those who prefer a balance of scenic day trips with well-placed local eats and overnight options that don’t require a five-star budget or a high pain tolerance. Bring your GPS, but maybe ignore it when something smells like bacon or looks like a side road to happiness.

Driftless Region: Wisconsin’s Hidden Motorcycle Gem

Route Overview

Tucked into the southwest corner of the state, the Driftless Area was untouched by glaciers during the Ice Age, which means it’s a geological misfit—with winding roads, deep valleys, and forested ridgelines. Think “Smoky Mountains-lite,” but with more cows and a strong chance of stumbling across an Amish bakery.

Start your route in La Crosse and head southeast along Highway 33—a favorite among motorcyclists—for its tight twisties and sweeping views. Make your way toward Wildcat Mountain State Park and loop back through Viroqua and Coon Valley.

Local Eats and Stays

• Kickapoo Corners Family Restaurant in Readstown is a small-town diner where the coffee is hot and the burgers are the kind of messy that require a fork halfway through.

• Hotel de Ville in Alma offers a vintage Americana vibe with motorcycle-friendly parking and walkability to a handful of excellent breweries.

Pro Tip: If you're riding a Can-Am Spyder like I am, Wildcat Mountain’s descent can feel like you’re riding a rollercoaster engineered by a dairy farmer with an attitude. Use engine braking and enjoy the ride—it’s one of the best in the state.

Door County Peninsula: Coastlines, Cherry Pies, and Lighthouses

Scenic Routes

Door County feels like riding through a Hallmark movie where everyone owns a fishing boat and wears flannel unironically. Start in Sturgeon Bay and ride up Highway 42, weaving your way through Egg Harbor, Fish Creek, Sister Bay, and finally Gills Rock at the tip of the peninsula. The ride itself is mellow, perfect for beginners or those of us who want to enjoy the view without constantly shifting gears.

What makes Door County unique is the proximity to both Green Bay and Lake Michigan. You’ll ride through stretches of shoreline, cherry orchards, and quiet lake towns that look like Norman Rockwell illustrations come to life.

Can’t-Miss Stops

• Wilson’s Ice Cream Parlor in Ephraim has been serving sundaes and burgers since 1906. If that isn’t a solid enough resume for a pit stop, I don’t know what is.

• Al Johnson’s Swedish Restaurant in Sister Bay has goats on the roof. That’s not a joke.

• White Gull Inn in Fish Creek is the place to stay for riders who want charming comfort, great breakfasts, and a safe spot to park the bike.

Don’t Miss: If you’re up for a little walking after a long ride, the Cana Island Lighthouse offers a gorgeous panoramic view—and a bit of a leg stretch climbing the tower.

Kettle Moraine Scenic Drive: Glacial Roads and Forested Bliss

Route Details

The Kettle Moraine Scenic Drive is a 115-mile route running north to south through eastern Wisconsin, following the glacial ridges and kettles that give the region its name. Begin near Elkhart Lake—which happens to be home to the legendary Road America racetrack—and ride south toward Whitewater.

This route is excellent for riders looking to mix some twisties with long stretches of scenic cruising. For Can-Am Spyder riders, it’s a joyride—smooth pavement, gentle grades, and enough turns to keep you smiling but not stressed. Think of it as yoga, but with torque.

Great Stops and Gear

• The Tiki Bar at Sunset on Elkhart Lake is a legendary chill-out zone after a long ride. Sip a drink, dip your feet in the water, and watch the sunset burn over the lake.

• The Osthoff Resort in Elkhart Lake offers rider-friendly accommodations with secure parking, lakefront dining, and suite-style rooms perfect for unwinding after a scenic ride. It’s also just minutes from Road America, so you can soak in some motorsports history while you’re there.

• Road America’s Paddock Shop has surprisingly solid motorcycle-themed gear if you're looking for a souvenir.

Midwest Soul, Open Roads, and a Little Bit of Cheese

The joy of motorcycling (or three-wheeling) through Wisconsin is less about speed and more about immersion. The rolling countryside, the friendly small towns, the smell of pine and grilled bratwurst—it’s a sensory experience that grounds you and, frankly, reminds you why you ride in the first place.

For me, switching from two wheels to a Can-Am Spyder RT was a game-changer. It gave me the confidence to keep exploring, to take on those twisty descents and uneven roads without white-knuckling my way through. Wisconsin’s roadways have become a favorite of mine for exactly that reason—they’re approachable but never boring.

If you're planning your next ride, don’t overlook this Midwest gem. Wisconsin is where winding roads meet butter burgers and where you’re just as likely to get directions from a guy on a tractor as a GPS. And trust me, the guy on the tractor is probably right.