For Harley-Davidson fans, Milwaukee is unquestionably one of the leading motorcycle destinations in the country—if not the world.
This is the birthplace of the famed Bar & Shield brand, which launched in 1903. And Harley has never traveled far from its roots. Harley’s corporate Wisconsin headquarters, located at 37th Street and Juneau Avenue, is not too far from the site of Harley’s original shop.
At the heart of this vibrant Midwestern city is also the legendary Harley-Davidson Museum, celebrating the brand's storied history with interactive exhibits, tours, and heartland-themed events like BBQ & Blues by Bulleit Bourbon and a Thursday Bike Night concert series featuring hits from local and regional bands.
Besides the Harley-Davidson-focused attractions, our favorite Milwaukee area attractions include Lakefront Brewery, Milwaukee Public Market, and the historic Third Ward neighborhood's bustling nightlife.
Whether renting a Harley-Davidson or any other bike, Twisted Road has thousands of available motorcycles for rent from passionate owners looking for you to enjoy everything Milwaukee has to offer.
Where to Rent a Motorcycle in Milwaukee
Without a question, the best way to deal with motorcycles in Milwaukee is to rent one from Twisted Road. Twisted Road also has a dedicated motorcycle rental app where you can book rides, negotiate rates with Milwaukee area owners, and be in full control of your riding experience.
What are the Best Motorcycle Rides in Milwaukee?
Here are our favorite motorcycle routes in and around Milwaukee:
Holy Hill Loop
This 60-mile round trip ride takes you through some of Milwaukee's most impressive architectural and natural wonders, with stops at the Holy Hill Basilica, Kettle Moraine, and plenty of non-descript rural landscapes.
-
Distance: 60 miles round trip
-
Road Conditions: Smooth and well-paved roads with a few twists and turns
-
Scenic Highlights: Holy Hill Basilica, Kettle Moraine Scenic Drive
-
Restaurants/Hangouts: Iron Ridge Inn restaurant, Sandy's Barton Cafe, The Dockside Deli
Kettle Moraine Scenic Drive
If you're a big fan of rolling hills and quaint small towns, then the Kettle Moraine State Forest is your route. Right alongside Kettle Moraine State Forest and tour its rustic roads to capture some off-the-beaten-path action with plenty of hiking and picnicking opportunities. Remember to explore the Kettle Moraine region, known for its exceptional glacial activity dating back to a past era with the last Ice Age.
-
Distance: 150 miles round trip
-
Road Conditions: Curvy roads with elevation changes
-
Scenic Highlights: Kettle Moraine State Forest
-
Restaurants/Hangouts: The Chancery, Fox and Hounds Restaurant and Tavern, Stollen’s Hogg Alley
Rustic Road 35 Loop
This 40-mile round-trip route takes you through twists and turns along scenic rural roads on Rustic Road 35. Revel in the many classic American restaurants in the area with biker-friendly vibes, such as Stolley's Hogg Alley and The Mineshaft Bar and Restaurant.
-
Distance: 40 miles round trip
-
Road Conditions: Well maintained with designated viewpoints
-
Scenic Highlights: Historic farmsteads, wildlife viewing areas, quaint villages
-
Restaurants/Hangouts: Stolley's Hogg Alley, The Mineshaft Bar and Restaurant, Sandy's Barton Cafe, The Dockside Deli
Milwaukee Motorcycle Hangouts
Alongside the city's industrial legacy, Milwaukee has placed a premium on motorcycling culture. It is the home of Harley-Davidson, and numerous annual events celebrated by motorcycle enthusiasts worldwide, such as the Milwaukee Rally and the Mama Tried Motorcycle Show.
There are plenty of biker-friendly bars, even alongside the Lake Michigan shoreline.
Here are our favorite motorcycle hangouts in Milwaukee:
Heaven’s Devils Motorcycle Club
Formed in August 1964, the Heavens Devils Motorcycle Club is celebrating more than 50 years of motorcycle culture and tradition. It is one of the oldest motorcycle clubs in the state, regularly holding events such as summer bashes with a $15 entry fee and unlimited beer by local and regional artists.
Harley-Davidson Museum
No motorcycling trip to Milwaukee is complete without a visit to the Harley-Davidson Museum. From a small workshop to a global powerhouse, Harley-Davidson evokes spirit worldwide for its beginnings, iconic mastery of vintage motorcycle production, and a hearty spirit greater than anything its iconic "Bar & Shield" shape can convey.
Milwaukee Weather and Riding
Before any motorcycling trip to Milwaukee, know it's best to go during late spring to early fall, where you can experience vibrant fall foliage and the most favorable riding conditions with longer daylight hours.
Always wear appropriate protective gear, starting with a helmet, sturdy boots, and a weather-appropriate jacket and gloves.
Perform pre-ride checks, quickly checking for tire pressure, brake responsiveness, no burnt-out bulbs, and other components. Along with safety checks, always ride defensively and assume that nearby drivers cannot see you well.
Milwaukee Motorcycle Laws
Be mindful of Wisconsin's helmet and eye protection laws. Although no universal helmet is required, it's highly recommended.
And lane splitting and lane filtering are illegal.
For Wisconsin residents to obtain a class and motorcycle license, they must be at least 16 years of age, starting with a motorcycle instruction permit with restrictions for practice riding. The Wisconsin Department of Transportation (WisDOT) also offers an optional motorcycle safety course.
From there, obtain your class M license.
Lastly, once you've obtained your license, there are no passenger age restrictions (all passengers must be at least five years old, with additional requirements to guarantee your safety).
Preparing for your Milwaukee Motorcycle Trip
Plan your route in and around the Milwaukee area before you visit Twisted Road and browse hundreds of available listings for rentals from Harley-Davidsons to Ducatis.
Have no gear? No problem! Twisted Road can also hook you up with gear. We can work with owners to offer you the needed gear, including jackets and helmets.
Live in Milwaukee? Earn Extra Money Renting Out Your Motorcycle
As one of the leading peer-to-peer motorcycle rental marketplaces, Twisted Road makes it easy for owners and riders to connect and negotiate rental terms on a bike with one another.
Plus, all owners earn 70% of profit, which means accruing total earnings of $1,000 will return $700 to your pocket. It's an excellent deal in a world where it's often 50/50 or worse.
