Adventure is out there!

Lifetime H.O.G.^® member Nancy Webb describes herself as a traveler, but that barely begins to describe her long-distance riding exploits.

Nancy Webb, a U.S. Air Force veteran from northern Kentucky, caught the Harley bug back in 2012 when she bought a Sportster 1200 Custom (named Delilah) with the help of the military sales program. Her long-distance adventures didn’t start until August 2020, after months of being cooped up due to Covid-19, and losing her dad.

“I took off for my first Sturgis trip on my 2018 red Street Bob^® called Willie,” says Nancy. “I was gone for 49 days, hit 14 states, and rode 10,000 miles. That was it—I was hooked on long-distance riding!” 

Since then, she has accumulated 300,000 miles with H.O.G.^®, completing the Ride 365™ 50 Rides, One Nation challenge, all H.O.G. 10/15 Rides for … between 2021 and 2025, as well as taking part in the Motorcycle Grand Tour of Texas, PNW Grand Tour, Tour of Honor, RTE-X-USA (Ride To Eat), Hoka Hey Challenge, numerous Iron Butt 1,000- and 1,500-mile rides. She also came first in the 2024 H.O.G. Dealership Check-in Challenge after achieving second place each year between 2021 and 2023.

“I’m an adventurer and a traveler,” says Nancy. “After I ran away the first time at the ripe old age of three, my mom told my dad, ‘The backyard will never be big enough for her!’ And she was right!”

Nancy’s most memorable long-distance experience so far has been the 2022 Hoka Hey Motorcycle Challenge. Participants cover approximately 10,000 miles over several days; they have to sleep next to their bike overnight and are discouraged from using sat nav.

“It’s exhausting, both physically and mentally, and it pushed me to my limits at the time,” says Nancy. “The Hoka Hey is designed to be a demonstration of the warrior spirit of the Sioux, and it certainly challenges you. On one occasion in Arizona, when it was 110 degrees in the middle of nowhere, all I wanted to do was stop, throw the bike down, and walk away. By the time I got to the next gas station, I had mentally hurdled that obstacle and was able to continue. The challenge is every two years, so, in that time, you forget about some of the pain, which is why I’m already preparing for the next one in 2026!

“I don’t just ride for the sake of it; I need a goal, a purpose,” says Nancy. “To succeed at destination challenges requires flexible planning, careful routing, quite a bit of stamina, patience and cash, as well as the support of family and friends.”

A reliable two-wheeled companion is also essential, and Nancy’s steed of choice is a Harley. “After a season of riding my first Harley, Delilah, I purchased a red 2013 Night Rod, ‘Roxanne.’ I had both until 2018, and traded them in for my Street Bob, Willie, which I traded in four years later with 144,000 miles on him.”

“I currently have a 2022 Low Rider^® El Diablo, ‘Luci’ , short for Lucifer, and a white 2020 Road Glide^® Limited, ‘Michael’ , as in the archangel, that I bought used in 2024. Luci has about 65,000 miles on her now, while Michael has about 43,000 miles on him. The two of them are a reflection of my tendency to go from one extreme to the other in pretty much everything I do!”

Nancy’s riding time this year has been limited due to buying a house, but she has still managed to complete Saddle Sore and Bun Burner rides (1,000 miles in less than 24 hours and 1,500 miles in less than 36 hours, respectively). Next year, Nancy and Michael will attempt to become members of the Iron Butt Association’s 100K Club by riding 100,000 miles in one calendar year, while raising money for charity. She’s also taking on the Hoka Hey Motorcycle Challenge once again, as well as attending most (if not all) H.O.G. rallies.

“I’ve travelled by plane, train, automobile, bus, tram, van, ship, zipline, car seats floating on a barge—you name it,” says Nancy. “But motorcycling beats them all. Just you and the bike, music mixing with the machine, wild wind wailing around you … it’s nirvana!”

Follow Nancy here.

Nancy’s top three tips for long-distance riding

• While Roadside Assistance includes tow coverage, it’s always a good idea to review your plan details to ensure you’re covered for longer-distance tows if you travel frequently.
• Carry cold-weather gear regardless of the time of year. Snow is possible all year when you get into elevation.
• If you can shave five minutes off each gas stop, over the course of a full day, you can gain an extra hour for sleep (thanks to ultra-long-distance rider Chris Hopper for this tip).

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