Ride & Rally: Sportster Cross Country MN to FLA Ep 1

Cross Country Sportster Ride Minnesota To Milwaukee

The entire trip of riding my Sportster across the country was spawned from a few desires.
1. I’m always looking for ways to show that Sportsters are not just “bar hoppers”.
2. I wanted to ride my bike on the Tail of the Dragon.
3. I have always wanted to “Take My Harley Home” riding it to Milwaukee, the home of Harley Davidson.
Put those three together and I soon realized I was about to ride my Sportster across the country, and it was going to start with a ride to Milwaukee.

When staring at a map trying to figure out a route for any ride, I usually try to look for a two lane blacktop with a view which usually ends up coinciding with elevation changes or along a river. In this case, that would take me down Wi-35, also known as Great River Road. It’s a scenic road I know very well from Prescott to Pepin as it’s my number one go-to ride out of the Twin Cities. What I hadn’t seen though was the additional 130 miles of Wi-35 south of Pepin following the river into the town of Prairie Du Chien.

As we all know, riding a motorcycle isn’t just for getting from point A to point B but the magic is in taking our time to see everything along the way. On the way down to Prairie Du Chien, a lunch stop in Wabasha was in order. Wabasha sits on the Minnesota side of the river and is only a short bridge away from Great River Road. Not only is Wabasha a classic American small town but it is also the home of Slippery’s Tavern, made famous in the movie Grumpy Old Men. Photos of the movie and props adorn the walls while the riverside dining view of the Mississippi River makes it the perfect mid day stop to stretch your legs and fill your stomach.

Continuing down Wi-35 after lunch offered up expansive views of the river and a wonderful afternoon of riding two lane blacktop all the way down into Prairie Du Chien to stop for the evening. Prairie Du Chien is often referred to as Wisconsin’s second oldest city and was a popular gathering point for fur traders due to the convergence of the Mississippi River and the Wisconsin River just south of the town. Today, it’s filled with smiling locals and great watering holes to sit back and relax in after a day of riding.

Coming out of Prairie Du Chien the next morning, the front tire was headed straight towards Milwaukee. It’s a beautiful ride through Wisconsin farmland taking 18 east for a few hours before linking up with Interstate 94 in Madison to super slab it into Milwaukee and hit the Museum.

Before visiting the Museum though, I had to take a stop at their HQ on Juneau Ave. While they ceased production at the Juneau Ave. location in the 70’s, they still have the headquarter offices, prototyping, and Harley Master Tech classes there. What some people don’t know though is the location of the Juneau factory, built in 1910, is only a short distance from the site of the original Davidson home and shed in which the company was started. So close in fact, it’s only 1,320 feet away at 38th and Highland which happens to be the intersection where you turn into Harley Davidson. Heritage is big not only with Harley riders but also the MoCo itself. So much so that after moving out of the shed to build a factory in 1910, Harley remains operating out of the same building today that offers up views of the site of the original shed. While the Juneau Ave. building is not open to the public, you can swing by for a photo with your bike at the place where it all started before heading over to the Museum.

Upon pulling into the Museum, the place was packed! I previously did not know but they were hosting demo rides on many of the new 2021 models including the Pan America. Having only seen the Pan America in photos it was great to see it in person and take it for a rip. I tend to be a hesitant traditionalist when it comes to accepting new styles and new technology and the Pan America showed me, just like the new monoshock Softail did in 2018, that change can be good and good things are coming out of Milwaukee. My first impression on the Pan America was that it does not feel like a Harley at all. With a higher ride height, foot controls placed further back, and an overall upright feel, it all felt foreign for the first couple of blocks. The Pan America has four modes in which the bike’s ECM will change how the bike performs. While the wet/rain mode for less than ideal conditions and your regular everyday riding mode are fairly stock, it is sport mode and off-road mode that got me hooting and hollering. The amount of acceleration in sport mode out of the new Revolution Max 1250 engine laying down 150 horsepower at 94 ft.-lbs of torque is incredible. To test off-road mode I had to find some potholes. Luckily for this test, Milwaukee streets have some of the best potholes around and I was shocked with the ride comfort in off-road mode turning otherwise back breaking craters into mellow dips. After stepping off wishing my Sportster had both sport mode and off-road mode, I headed into the Motor Bar there at the Museum for some of their fantastic barbecue before heading in to soak up Harley’s history.

If you have not been to the Harley Davidson Museum, you are in for a real treat. It is one of the best motorcycle museums in the world and a must stop for any Harley enthusiast. The overall flow of the museum is set up to bring you through Harley history from 1903 up until today. One of the first bike’s you see is “Serial Number One”. While, it was not the first Harley Davidson in existence, that would be a prototype, it is the first Harley that was ready for sale and it is known to be the oldest Harley Davidson in existence today. From there, there is a giant line up of motorcycles taking you through the early 1900’s up through the 40’s era Knuckleheads with many of the different models and paint on display. To celebrate Harley’s racing heritage, there is a massive board track racing display with early board track bikes. Venturing downstairs we switch to the post-war years of Harley introducing the Panhead, the Shovelhead, the Sportster and the rise in Harley’s increased popularity with memorabilia from the 60’s counterculture movement. The history of display bikes goes all the way up through the 2000’s celebrating the MoCo’s progression while keeping a nod to the past.

Serial Number One

1936 Knucklehead

After picking my jaw up off the floor, my stomach started growling again and it was off to Fuel Cafe. Fuel Cafe is a short mile or two ride down 5th street from the museum and is one of the best spots for bike nights in Milwaukee and general moto shenanigans. Fuel was started by Scott Johnson who also started the Mama Tried Motorcycle Show that has become one of the largest and most respected shows in the country. We were lucky enough to cover the show in Fix My Hog’s Ride and Rally 2018 and 2019 when it nearly doubled in size and moved to The Eagles Ballroom.

The only thing left to do after an epic day of riding and staring at priceless rare and vintage Harleys is turn in for the night. The Iron Horse Hotel is located between the Museum and Fuel Cafe making for the perfect place to stay and recharge. The Iron Horse Hotel is a motorcycle centric hotel geared towards riders and wrenchers with not only a great atmosphere and spacious rooms to accommodate all the gear but covered dedicated motorcycle parking right next to the front door. They even have a custom digger style Shovelhead that adorns the lobby and greets you as you walk in.

Every time I visit Milwaukee I come away with a deeper love for the brand and the history behind it and this trip was no exception. Riding your bike to Milwaukee and taking it all in only deepens the bond between you and your Harley and I would put it as one of the top rides to do if you get the chance.

Watch The Full Ride & Rally Episode Here

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One Response to “Ride & Rally: Sportster Cross Country MN to FLA Ep 1”

  1. Jose Moreyra

    Awesome !