The rumble of a V-twin beneath you, the open road stretching out, and the promise of a weekend steeped in motorcycle culture – that’s a recipe for pure bliss. This past weekend, my journey began like many of yours do, with a familiar packing routine and the anticipation of hitting the highway.
My destination? Road America, for the thunderous spectacle that is King of the Baggers. But before the track action, there was a whole adventure to unfold, starting right from the Twin Cities. I pointed my front wheel east on Friday, eager to escape the daily grind. The initial leg of the ride took me to Hudson, Wisconsin, a convenient and scenic meetup point. It was there I linked up with my buddy, a familiar face to many of you who follow the V-Twin scene – none other than the man behind the camera and handlebars, RidingFish. If you haven’t checked out his YouTube channel, you’re missing out on some genuine two-wheeled adventures and insights.
From Hudson, we carved our way through the picturesque Wisconsin landscape, the miles melting away under our tires. Our paths converged as we approached our lodging for the night; I opted for a hotel in Manitowoc, while RidingFish settled into Plymouth, a bit closer to the track. However, the evening wasn’t destined for solitude.
As dusk settled, we reconvened for dinner, and what a gathering it turned out to be! The motorcycle community truly is a tight-knit family, and serendipitous meetings are always part of the charm. Over a shared meal, we had the distinct pleasure of meeting the crew from the Throttle & Iron podcast. Their candid conversations and deep dives into all things motorcycle are always a fantastic listen. It was a great opportunity to swap stories, talk shop, and just generally soak in the camaraderie that only fellow riders truly understand. The food was good, and the conversation flowed as easily as the cold drinks. As the clock neared 9 PM, I bid farewell, as the rain had started and I had an early start planned for the next day, making the ride back to my hotel in Manitowoc.
Saturday: A Milwaukee Meetup and the Road to Road America
Saturday dawned early, and by 4:45 AM, I was up and on the road, heading from my Manitowoc hotel towards Indian Motorcycle of Metro Milwaukee. The early morning roads were quiet, offering a serene start to what would become a day packed with V-twin excitement. Along the way, I spotted a familiar Indian Challenger ahead – it was my friend Kevin, also making his way to the dealership. We linked up and rode the final ten miles together, the sound of our engines harmonizing as we approached our destination.
Upon arrival at Indian Motorcycle of Metro Milwaukee, we were greeted by the owner, Rob Schopf. He was incredibly generous with his time, giving us an awesome tour of the dealership. What truly stood out was his performance shop, “2 Boss Performance.” It was clear this isn’t just a dealership; it’s a hub for riders who demand more from their machines, a place where passion for performance truly comes alive.
After the fascinating tour, it was time for the main event: the group ride to Road America. Approximately 100 motorcycles gathered, a truly impressive sight as we prepared to roll out. The ride itself was about 100 miles, a fantastic convoy of V-twins rumbling through the Wisconsin countryside, all headed for the same thrilling destination. The sense of community on a ride like that is simply unmatched.
Once we arrived at the iconic Road America track, Indian Motorcycle had truly rolled out the red carpet. They provided passes for entry, a welcome lunch, and even a swag bag – a thoughtful touch that capped off the excellent hospitality.
Then, it was time for the main event: King of the Baggers! The racing was absolutely amazing. On day one, May 31, 2025, Kyle Wyman, riding for Harley-Davidson x Dynojet Factory Racing, took the win in Race 1 with a total time of 11:38.330 over five laps, and a best lap of 2:18.249. He was followed by his teammate James Rispoli, and then Tyler O’Hara on an S&S/Indian Motorcycle.
While I had to depart early on Sunday morning, the second day of racing, June 1, 2025, proved to be just as thrilling. Troy Herfoss, representing S&S/Indian Motorcycle, claimed victory in Race 2 with a total time of 11:40.910 and a best lap of 2:18.382. James Rispoli on a Harley-Davidson x Dynojet Factory Racing bike finished a very close second, just 0.229 seconds behind, followed by his teammate Kyle Wyman in third.
As Sunday morning arrived, it was time to point the bike west. The 350-mile ride home was a solo affair, offering plenty of time to reflect on the incredible weekend, the camaraderie, the thunder of the bikes, and the raw speed of the King of the Baggers. Sometimes, that alone time with your machine on the open road is exactly what you need to recharge. It was a fantastic weekend filled with good company, incredible motorcycles, and the thrill of the race. I’m already looking forward to the next adventure!
