THOUSANDS OF YOU WENT THE EXTRA MILE DURING THE 2025 HARLEY-DAVIDSON LET’S RIDE CHALLENGE

Does Alex have tips for anyone entering the 2026 challenge? “If I’m going to win again, I don’t want to share too much advice,” he laughs. “But, seriously, don’t think about it too much—just get out and ride and do the dealership check-ins. I kind of got stuck in analysis paralysis for a while, thinking I needed to go on this huge adventure, but it’s not necessary. If you love riding, you’ll enjoy it no matter what. If a five-minute ride turns into five hours, so be it!”

Gold Tier (2,501 - 4,000 miles)
Grand Prize 2025 Street Bob®
Winner: Andrew Peterson from Fort Myers, Florida

Andrew Peterson has been riding motorcycles since the late ’70s, inspired by reading Zen and the Art of Motorcycle Maintenance, and seeing Easy Rider. He began his Harley-Davidson journey on a 2002 Sportster® XL1200C Custom and joined H.O.G. in 2000. Andrew’s wife bought him a Road King® as a birthday present, soon followed by a Road Glide for the longer trips—including a ride to Sturgis with his poodle, Gigi.

“The Let’s Ride Challenge came up on my social media feeds and I went straight to Rockstar Harley-Davidson in Fort Myers to find out more,” says Andrew. “I really got into the program when I traveled to New England, and then when I went to my old stomping grounds in Washington D.C., and the staff at Battlefield Harley-Davidson in Gettysburg told me I could start accumulating prizes like the challenge coins.

“I didn’t expect the call to tell me I’d won, although I’d read the rules and realized it really was a game of skill, not chance, so I knew I was in with a shot. My wife was amazed!”

Andrew intends to take full advantage of his new Street Bob. “I will be riding it, for sure. I regret selling the 1200C, so this is the replacement—light, easy to ride, but way quicker and smoother than the rigid-mounted XL.”

“To me, riding is a visceral experience where you’re really tuned into the curves of the road with the wind in your face. The Harley community is great too—you meet everyone from lawyers to outlaws. We all have something in common. Join the ride, enjoy the ride—after all, the ride is the destination!”

Platinum Tier (4,001 - 5,500 miles)
Grand Prize 2025 Fat Boy®
Winner: Doug Sawyer from Shreveport, Louisiana

Doug Sawyer, a semi-retired physician from Shreveport, was motivated to enter the challenge when dealer staff told him about it at a local H.O.G. Chapter meeting. “It piqued my interest when I realized this was a contest of skill and had real prizes,” he says. “It took a bit of time to grasp all the ins and outs, but that just added more drama. I told the dealer general manager that I thought I could really win this sucker! In fact, I put my reputation on the line when I told everyone I was going to win—and thankfully I did!”

Doug joined Harley Owners Group when he bought a 2024 Road Glide Limited 18 months ago and started racking up the miles.

“Accumulating the points is the most fun I’ve had on the Road Glide since I bought it, especially in the Smoky Mountains. The roads are exceptional, and you can ride for 100 miles in a dream state because it’s so beautiful.”

“I’ll be doing the challenge this year on my new bike, so come and catch me! Meanwhile, I’m just glad that I didn’t end up sticking my foot in my mouth when I told everyone I was going to win!”

Diamond Tier (5,501 - 7,500 miles)
Grand Prize 2025 Street Glide®
Winner: Justin Patterson from Mosinee, Wisconsin

Justin started riding in 2009 when he bought his first Harley—a 1999 Heritage Springer, a bike he says opened up a new chapter for him. Now on his third model, a Road Glide named ‘Whiskey Shark’, Justin has since covered much of America. “Owning a Harley and joining Harley Owners Group has introduced me to a whole new family, taken me out of my comfort zone, and opened a lot of doors. It has completely changed my life.”

Justin was looking forward to a normal riding season when Harley-Davidson announced the challenge. “I’m good friends with Tim Duffy, the founder of 1 Soldier 1 Dog 1 Team, and when I saw it was one of the participating charities, I immediately said, ‘I’m in,’ and signed up at my local dealer. I wore my 1 Soldier clothing when I rode to all the dealerships, attracting a lot of publicity. It has been overwhelming to get that much exposure for a small charity, and very rewarding.

Justin’s strategy was to visit as many dealers as possible, rather than just accumulate miles. “Every time I went for a ride, I plotted the dealer locations I needed to hit to optimize the points. I heard I’d won mid-November, when I’d just got back from Love Ride 34 in California. I was ecstatic.”

“My tip for anyone entering in 2026 is to make sure you fully understand how to accumulate the points—it’s the high score that wins.”

Black & Orange Tier (7,501+ miles)
Grand Prize 2025 CVO Road Glide
Winner: Jeff Guynes from Montrose, Colorado

Jeff, a Harley Owners Group member for 25 years, was the runaway winner of the Black & Orange category. It’s fair to say that he likes to ride, having racked up more than 140,000 miles on his 2014 Ultra Limited® in the last six months.

“I have 314,000 miles on my bike right now, and it all came about when I met a guy at a H.O.G. event in 2000 with an Iron Butt pin. I didn’t know what it was, but that set me off.”