Best Motorcycle Tours and Routes in Wisconsin
Evan Rally
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Wisconsin offers motorcyclists a diverse riding experience, from the rolling hills of the Driftless Area to the scenic shores of the Great Lakes. The prime riding season typically spans from May through September, when the weather is most accommodating.
Some Legalese for Wisconsin:
- Helmet Laws: Wisconsin enforces a partial helmet law. Riders and passengers under 18, as well as those with instructional permits (regardless of age), must wear DOT-approved helmets.
- Lane Splitting/Filtering: Illegal statewide. Motorcycles must occupy a single lane, and riders cannot weave between lanes or pass stopped vehicles.
- Passenger Rules: Only one passenger allowed, provided the motorcycle has a dedicated seat and foot pegs. Passengers must be ≥5 years old and wear helmets if the rider is under 18 or holds a permit.
- Speed Limits: Highway speed limits are capped at 70 mph.
Did we miss your favorite Wisconsin tour or riding route? Let us know in the comments!
Tours & Guided Rides in Wisconsin
Considering Milwaukee is the home of Harley Davidson, Wisconsin is the starting point for three iconic Route 66 motorcycle tours offered by EagleRider.
Route 66 Motorcycle Tour – Harley-Davidson VIP Experience (Guided)
This 17-day journey covers the iconic Route 66, starting in Milwaukee and concluding in Los Angeles. Riders will traverse historic towns, scenic landscapes, and enjoy exclusive access to Harley-Davidson experiences.
Route 66 Motorcycle Tour – Harley-Davidson VIP Experience – 10 Day (Guided)
A condensed 10-day version of the classic Route 66 tour, offering a comprehensive experience of this legendary highway – but not all the way to the coast.
Route 66 Self-Guided Motorcycle Tour – Harley-Davidson Museum
For those preferring flexibility, this 17-day self-guided tour allows riders to explore Route 66 at their own pace, starting from Milwaukee.
Additionally, platforms like Rider’s Share offer a few day ride experiences in the Driftless region and along the Lakeshore. Riding with a local is a great way to see the area!
For a personalized riding experience, consider booking a tour through It’s Better On The Road’s custom tour planning team, who can tailor a journey to your preferences.
Great Motorcycle Routes in Wisconsin
Wisconsin offers motorcyclists a variety of scenic routes that showcase the state’s natural beauty and diverse landscapes. Here are some of the top rides over 40 miles, each celebrated for its unique appeal:
Great River Road (WI-35)
- Estimated Distance & Ride Duration: Approximately 270 miles; plan for a full-day ride or multiple days to fully appreciate the route. La Crosse is a beautiful small town on the Mississippi to spend a night in.
- Difficulty Level: Intermediate
- Road Conditions & Surface Type: Well-maintained paved roads with a mix of gentle curves and straight stretches.
The Great River Road, following WI-35, traces the Mississippi River from the outskirts of Minneapolis down to La Crosse, WI – but the curves extend all the way to Madison. This is Wisconsin’s famous Driftless region, with bluffs that make the rest of the Midwest blush with envy. Riders are treated to expansive river vistas, towering bluffs, and charming historic towns. Notable points of interest include Perrot State Park, offering hiking trails with panoramic views, and the city of La Crosse, known for its vibrant riverfront and cultural attractions. Don’t miss the prime rib at The Freighthouse Restaurant.
Kettle Moraine Scenic Drive
- Estimated Distance & Ride Duration: Approximately 70 miles; typically a 1.5 hour ride.
- Difficulty Level: Intermediate
- Road Conditions & Surface Type: Primarily paved roads with numerous 90 degree turns and elevation changes; some sections may have narrower lanes.
This iconic route traverses glacial landscapes in southeastern Wisconsin, passing through six counties. Highlights include the Holy Hill National Shrine, a neo-Romanesque basilica with panoramic views, and Old World Wisconsin, an open-air museum showcasing 19th-century immigrant life. The drive also features kettles, kames, and eskers shaped by ancient glaciers
Cut this route any way you like – there isn’t one road cutting through this forest, but rather a ton of gridded options to choose from. This is a nice day trip from Milwaukee.
Door County Coastal Byway Loop (WI-42 and WI-57)
- Estimated Distance & Ride Duration: 90-mile loop; approximately 2 hours without stops.
- Difficulty Level: Beginner
- Road Conditions & Surface Type: Smooth, well-maintained paved roads with gentle curves; suitable for riders of all levels.
Looping around the Door Peninsula, this byway offers picturesque views of Lake Michigan and Green Bay. Riders can explore quaint coastal villages, visit the Cana Island Lighthouse, and enjoy the serene landscapes of Peninsula State Park. Curvy Highway is a sight to see!
Highway 33 to Wisconsin River Loop
- Estimated Distance & Ride Duration: Approximately 252 miles; about 5.5 hours – but there are many ways to shorten it down to as little as an hour or two.
- Difficulty Level: Intermediate
- Road Conditions & Surface Type: Paved roads with a mix of straight sections and tight curves, especially around Wildcat Mountain.
This one is for all of you dads at the Wisconsin Dells: a guys trip could be any part of this loop through the forests and foothills of Wisconsin via Highway 33 up to La Crosse, then down the Mississippi before taking a turn along the Wisconsin River and back to the Dells. This is an all day trip from the Dells or from Madison, but every second of it is enjoyable; no boring straight highway to reach twisties.
Also doable from Madison (adds 50 miles).
Highway 55 and 32
- Estimated Distance & Ride Duration: Approximately 115 miles; around 2 hours.
- Difficulty Level: Intermediate
- Road Conditions & Surface Type: Well-paved roads with a combination of wide curves and straight stretches; heavily forested areas may have shaded spots.
Highway 55 provides a ride through rolling hills and alongside the Wolf River. The southern portion is full of twists and turns, while the northern section offers open stretches. The route closely follows the Wolf River, presenting beautiful river scenery and multiple lakes along the way.
Each of these routes offers a unique glimpse into Wisconsin’s diverse landscapes, ensuring memorable rides for motorcyclists of all levels.
Special Riding Areas in Wisconsin
Wisconsin boasts several sub-regions and unique areas that offer motorcyclists exceptional riding experiences, each with its own distinct allure.
1. Driftless Area
Located in southwestern Wisconsin, the Driftless Area is characterized by its unglaciated terrain, featuring deeply carved river valleys, rolling hills, and rugged landscapes. Motorcyclists are drawn to its winding roads that meander through picturesque farmlands and along scenic waterways, offering both challenging rides and breathtaking vistas.
The Driftless Area is some of the best riding in the Midwest, with beautiful historic towns dotting the Mississippi and Wisconsin Rivers. I highly recommend it. It’s also conveniently between Minneapolis and Madison / Milwaukee, making it convenient if you’re trying to go from A to B.
The Highway 33 to Wisconsin River Loop as well as Great River Road (WI-35) routes above go through here.
2. Door County Peninsula
Extending into Lake Michigan, the Door County Peninsula provides riders with over 300 miles of shoreline, charming coastal towns, and lush orchards. The area’s winding roads, such as those along State Highway 42, offer scenic views of the lake and access to attractions like lighthouses and state parks, making it a favored destination for leisurely cruises. The Door County Coastal Byway route above goes through here.
3. Kettle Moraine State Forest
Situated in southeastern Wisconsin, the Kettle Moraine State Forest is renowned for its unique glacial landforms, including kettles, kames, and eskers. Riders appreciate the area’s zigzagging roads that traverse dense forests and rolling hills, providing both engaging rides and opportunities to explore natural attractions like the Parnell Observation Tower. I’ve included a route above that goes through Kettle Moraine.
For motorcyclists seeking to discover and navigate these scenic routes, the REVER route-finding app is an invaluable tool. Built by riders for riders, REVER offers hand-picked routes and the ability to track and share your favorite rides, enhancing your Wisconsin motorcycling adventures.
Renting a Motorcycle in Wisconsin
EagleRider, the biggest motorcycle rental company in the USA, offers multiple locations across Wisconsin. Keep in mind they’re seasonally open, usually beginning rentals on April 1st and ending in October.
- Milwaukee Airport: Perfect for fly and ride trips, this branch provides easy access to the best Wisconsin has to offer from the Driftless Region to the Kettle Moraine forest. Seasonally open from April 1st. There’s also an Oconomowoc branch just outside Milwaukee.
- Green Bay: Situated at Vandervest Harley-Davidson®, 1966 Velp Ave., this location is ideal for exploring the scenic Door County Peninsula or Highway 55.
- Chippewa Falls: This branch offers rentals for those looking to explore the heavily forested northern regions of the state, and the northern Driftless region.
EagleRider provides a diverse fleet of motorcycles, including popular models from Harley-Davidson, ensuring riders can find the perfect bike for their adventure.
Rider's Share: Peer-to-Peer Motorcycle Rentals
For a more personalized and often cheaper option, consider Rider's Share, a peer-to-peer motorcycle rental platform. This service connects motorcycle owners with renters, offering a wide variety of custom bikes across Wisconsin. Benefits of using Rider's Share include flexible booking options, comprehensive insurance coverage, and competitive pricing. Whether you're seeking a classic cruiser or a modern sportbike, Rider's Share provides an extensive selection to suit your preferences.
To explore available motorcycles in Wisconsin, visit Rider's Share Wisconsin Listings.
Weather & Tips for Wisconsin Riding
Wisconsin's diverse climate and natural environment present unique considerations for motorcyclists. Here's an overview to help you prepare for a safe and enjoyable ride through the Badger State.
Seasonal Weather Patterns and Temperature Ranges
- Spring (March to May): Early spring can be unpredictable, with temperatures ranging from the 30s to 60s°F (0-20°C). Rain is common, and occasional late snowfalls may occur. As May approaches, milder conditions prevail.
- Summer (June to August): Summers are warm and humid, with average highs between 75-85°F (24-29°C). July is typically the warmest month. Thunderstorms are frequent, especially in June, which is the wettest month.
- Fall (September to November): Autumn brings cooler temperatures, ranging from the 50s to 70s°F (10-25°C) in September, dropping to the 30s°F (0-5°C) by November. The season is marked by vibrant foliage, offering scenic rides.
- Winter (December to February): Winters are cold and snowy, with average temperatures in the 10s to 30s°F (-12 to -1°C). January is the coldest month, averaging 15.3°F (-9.3°C). Rentals are usually closed in the winter.
Typical Road Conditions and Seasonal Closures
Road conditions vary with the seasons. Spring may bring potholes and debris from winter, while fall can introduce wet leaves, creating slippery surfaces. Winter conditions often lead to snow-covered and icy roads, making riding hazardous. The Wisconsin Department of Transportation advises checking current road conditions before traveling. While Wisconsin doesn't have high-elevation passes that require seasonal closures, certain roads may close temporarily due to severe weather or maintenance. It's prudent to consult the Wisconsin Department of Transportation for the latest information.
Recommended Gear
Other than the usual helmet and appropriate motorcycle gear (jacket, gloves, boots, pants, airbag even…) you should be ready for cold in the forests and rain, especially in the spring and summer months.
Wildlife Concerns
Deer are prevalent throughout Wisconsin and pose significant hazards, especially during dawn and dusk. The risk increases during the fall mating season. Riders should remain vigilant in forested and rural areas. Other wildlife, such as raccoons and turkeys, can also present unexpected “obstacles”.
Speed Limits and Lane-Splitting Rules
Wisconsin's speed limits vary by road type:
- Interstates: 65-70 mph
- Highways: 55 mph
- Residential Areas: 25 mph
Lane-splitting, the practice of riding between lanes of traffic, is illegal in Wisconsin. Motorcyclists must adhere to standard traffic lanes and regulations.
Events & Rallies in Wisconsin
As the home of Harley Davidson, Wisconsin has no shortage of motorcycle events and rallies; many with a long history.
Here are some notable events scheduled for 2025:
- Mama Tried Motorcycle Show
- Location: Milwaukee, WI
- Dates: February 22-23, 2025
- Summary: An indoor invitational showcasing custom motorcycles from builders around the world, accompanied by Flat Out Friday flat track racing. If you’re a fan of “Easy Rider”, check this one out. And stay at the Iron Horse Hotel!
- Harley-Davidson Homecoming® Festival
- Location: Milwaukee, WI
- Dates: July 10-13, 2025
- Summary: An annual four-day celebration featuring live music, moto-culture events, and festivities honoring Harley-Davidson's heritage.
- Big River Rally
- Location: La Crosse, WI
- Dates: August 16, 2025
- Summary: Features guided rides, stunt shows, bike displays, live music, vendors, and food trucks along the scenic Mississippi River.
- Wisconsin Dells Rally
- Location: Wisconsin Dells, WI
- Dates: September 5-7, 2025
- Summary: Organized by the Wisconsin BMW Motorcycle Club, this rally includes scenic rides, social events, and camaraderie among riders.
- Northwoods Fall Ride in Tomahawk
- Location: Tomahawk, WI
- Dates: September 11-13, 2025
- Summary: A gathering featuring scenic rides through the Northwoods, live music, vendors, and community events.
- Slimey Crud Café Racer Run
- Location: Cross Plains, WI
- Dates: May 4 and October 5, 2025
- Summary: A biannual informal ride attracting café racer enthusiasts, with routes through scenic rural roads.
For a comprehensive and up-to-date list of motorcycle events in Wisconsin, you can visit CycleFish's Wisconsin Motorcycle Events Calendar.
These events offer a range of activities, from live music and vendor booths to charity rides and scenic group tours, providing something for every motorcycle enthusiast.
Get to Riding in Wisconsin
Wisconsin is a hidden gem for motorcycle enthusiasts, offering everything from the winding roads of the Driftless Area to the breathtaking shores of Door County. Riders can experience scenic byways like the Great River Road, challenging routes through Kettle Moraine, and vibrant motorcycle culture at legendary events like the Harley-Davidson Homecoming Festival. With a mix of well-paved highways, rustic backroads, and unforgettable rallies, Wisconsin is a dream destination for riders seeking adventure, history, and natural beauty.
Now that you’ve seen what Wisconsin has to offer, it’s time to hit the road! Whether you’re looking for a premium rental through EagleRider, a unique bike through Rider’s Share, or a fully customized motorcycle tour, we’ve got you covered. Our team at It’s Better On The Road specializes in creating unforgettable two-wheeled adventures tailored just for you.