The joy is in the journey

Words by Jeremy Pick

Eagan Norman combined his first long-distance road trip on his Street Bob^® with Ride 365^{^®} challenges and enjoyed every moment.

Eagan Norman would be the first to admit he’s a relative newcomer to motorcycling. He gained his license in 2019 at age 22 after receiving a Riding Academy class for Christmas, but he didn’t buy his first bike, a 2023 Harley-Davidson^® Street Bob^®, until March this year. He started working for H.O.G.^® in Milwaukee straight out of college in 2021, initially as a data analyst auditing the mileage program before taking on a full-time project manager role in December 2023, working primarily on the H-D member loyalty program. Talking to members participating in the program inspired Eagan to take part himself.

“A good friend bought a house in Denver, Colorado, where my family is from, and invited me to visit,” says Eagan. “I’ve been excited about getting this bike for the last six years, so there was no way I was leaving it at home. I also felt confident knowing there was a ton of support available to H.O.G. members, such as roadside assistance, in case anything went wrong, so I started planning the trip via the back roads. I’d heard so many good things about Ride 365 through my role at H.O.G. that I wanted to incorporate that into the journey too.”

So, eight weeks after getting his Street Bob, he embarked on his first epic road trip …

Wiebler’s H-D® check-in for the Dealership Photo Challenge

Day one: I left Port Washington, Wisconsin, at 8am. My dad, another Milwaukee rider, rode with me on his Ultra Limited^®, turning around after a quick lunch in Dubuque, Iowa. Dubuque is on the Mississippi River and that valley is gorgeous, so it was cool to ride south on the Mississippi for a while, following the Iowa/Illinois border before cutting back into Illinois.

One of the 15 Rides for ’25 challenge destinations is in Kewanee, the “Hog Capital of the world.” I arrived there late afternoon, and as I was also doing the Dealership Photo Challenge, I pulled over for a photo by the dealer sign at Wiebler’s Harley-Davidson^®. I was really touched when the team there came out to check that I was good to continue on the road, even though they had just closed. I’d planned to do my first 50 Rides, One Nation challenge in Donnellson, Iowa, the next day, so I found a cheap motel nearby and crashed out for the night. I’d covered 440 miles – my longest day of riding ever!

Day two: The Historic Hills Scenic Byway from Donnellson to Moravia showed me a greener side of Iowa than I’d seen before. Rolling through farmlands, in the early morning mist was a great start to the day. After taking a photo at the checkpoint in Keosauqua, it was time to plot a route and head to Grand Island, Nebraska. The weather cleared up in time for a sunset ride along the railways into town. One thing I noticed traveling by motorcycle is that everyone is more inclined to talk to you—I met some of the nicest people at gas stops in Iowa.

Day three: The Sandhills Journey Scenic Byway is one of the longest routes in the 50 Rides, One Nation challenge at 272 miles. It follows a singular road from Grand Island in the southeast corner of Nebraska to Alliance in the northwest corner, taking you through many remote expanses of land and a handful of towns with fewer than 100 residents. It’s a wonderful part of Nebraska, and a gorgeous, unexpected ride. Then it was off to Cheyenne, Wyoming, to add some more miles and another state to the journey.

Day four: I had a short drop from Cheyenne into Colorado. I plotted my course into Greeley, and as a lifelong Denver Broncos fan, I had to stop at John Elway Harley-Davidson^®. I did the Dealership Photo Challenge then had my mileage read for the Let’s Ride Challenge^™ Ride for Heroes. Every member’s mileage counts towards a donation of up to $1 million for the nine charities supporting our military, veterans, and first responders. I achieved my 1,000-mile milestone and was the first rider to achieve this goal at their dealership.

Before departing, a couple of the staff caught up to me to talk about the Street Bobs they ride, and the fact they’d never seen someone with so much packed onto one before. I then headed west to the entry point to Rocky Mountain National Park. From there, I rode through the Arapaho and Roosevelt National Forests, getting up to 9,500 feet above sea level before coming down through Golden and into Denver. It was great to do some mountain riding for the first time. I reached my friend’s place that afternoon after riding 1,494 miles—just six miles shy of that 1,500 milestone.