Grandmother Ditches Cruisers For Dual Sports To Ride The World

In a world where many might consider winding down their adventurous pursuits as they enter their late sixties, Debi Wilder, a retired education professional with a penchant for large Harley-Davidsons, has chosen a different path—one that led her to adventures across South America, Asia, and beyond on the back of dual sport and adventure bikes.

A mother of two and a grandmother of three, Debi found her passion for adventure motorcycling later in life: within two years after her 65th birthday, Debi left cruisers for dual sports with no previous off-road riding experience, proving that age is no barrier to pursuing one’s dreams.

From Stingrays to Softails

Debi’s journey into the world of two wheels began at a young age when she received her first vehicle—a lavender Stingray bicycle. The need for speed ignited within her, and by the age of sixteen, she was already hitching rides on boys’ motorcycles. In 2007, after a transformative cross-country trip on a friend’s Road King, she decided to take control and get her own motorcycle. In January 2008, at the age of 52, Debi purchased her first bike—an ’02 Harley Davidson Heritage Softail.

Her initial years were dedicated to street riding:  five months after acquiring her motorcycle endorsement and purchasing the Softail, Debi embarked on a transformative solo journey up the east coast from Central Florida, which she fondly refers to as a “Soulo” trip.

Grandmother Leaves Cruisers For Dual Sports To Ride The World

“This expedition served as an uncoupling from a detrimental relationship, unleashing newfound freedom and confidence on two wheels. Preferring the open road, I meticulously planned routes on backroads, exploring various states and Canadian provinces. By 2016, I had only three U.S. states left to traverse in the lower 48, plus Alaska. I discovered a piece of my soul on the endless asphalt ribbon that carried me up to Canada and back home; I returned different, a different I embraced enthusiastically,” Debi recalls.

Looking for New Adventures

In 2020, however, Debi felt a different call – one that beckoned her to venture off the beaten path. Suffering from cabin fever after a difficult period during the Covid quarantine, Debi packed her Softail and left for another solo cross-country trip, yet this time, something was missing.

As she crossed the Continental Divide, she realized she had ‘been there, done that’ more than once. “This was my 5th cross country trip, and although I could never claim to be bored on my Harley, I realized my soul was screaming for something new. I wanted to feel that ‘pink cloud’ feeling I had when I first started riding”, Debi recalls.

Grandmother Leaves Cruisers For Dual Sports To Ride The World

Over the previous year, Debi had begun following social media accounts of world riders like Kinga “On Her Bike” Tanajewska and other female riders traveling and touring faraway countries on adventure bikes. Hearing stories of international adventures and reading travel books like “Tales from South America,” Debi felt inspired.

“The adventure riders I followed on social media looked like they were enjoying the hell out of riding. I was interested in international travel as well; adventure riding felt new and appealed to my sense of adventure which seemed to have dulled somewhat with my street riding. And so, on that trip to Arizona, I decided that I would take on adventure riding. I mean, how hard could it be, right? Ha!” Debi smiles.

The following September, she booked a two-day adventure riding course at the BMW Riding Academy in Greer, South Carolina. This was her first year of retirement from teaching; Debi was 65 years old, and everyone, including her partner, thought she was crazy. “But, as always, he was supportive,” Debi shares.

Grandmother Leaves Cruisers For Dual Sports To Ride The World

Her first experience tackling off-road trails on the GS didn’t go smoothly, however.  Debi felt she was thrown into the deep end with a big bike: “I spent more time picking the GS off the ground than riding,” she laughs.

Into the Wild: Colombia

Despite a challenging first dirt training experience, Debi was undeterred. Soon after, she reserved a spot on a women’s dual-sport tour of Colombia, having been reassured that the off-road trails would be entry-level. Just to be on the safe side, Debi booked two extra days before the start of the tour to familiarize herself with the motorcycle she’d be riding in Colombia – a Honda XRE 300 – and the local traffic.

Grandmother Leaves Cruisers For Dual Sports To Ride The World

Gear was another learning curve: having no previous off-road experience, Debi asked questions online and assembled an inexpensive kit of knee pads, body armor, and boots. Not wanting to invest in pricey adventure riding gear just yet, Debi felt there was room for improvement afterward: “I bought inexpensive gear and cheap boots for my first trip; I felt like the bastard stepchild with my raggedy gear, but I didn’t want to spend the money on gear until I decided whether I wanted to pursue ADV riding further. I literally tossed my boots in the trash bin at the hotel in Medellin at the end of the tour!” Debi shares.

In Colombia, the combination of pavement and off-road riding proved to be a perfect introduction to adventure riding for her. Debi admits to feeling terrified on the first day of hitting the dirt, but the adventure proved to be exactly what she was looking for.

“It was the kind of thrill I sought, searching for that ‘pink cloud’ feeling! In Colombia, I navigated dirt, gravel, and mud, dodged chickens, cows, horses, people, dogs, and buses painted with the likeness of Jesus – and I loved every minute of it. Yet again, as I did long ago on my first ride up the East Coast, I discovered a piece of myself and a new level of confidence…on dirt and gravel! I also realized I loved being a moto tourist. I was hooked,” Debi explains.

Connecting with other women with a similar passion for riding, bonding over the adventure, sharing meals and sleeping arrangements along with fears, triumphs and all that entails added to the allure of adventure travel. Debi explains she has met and made lifelong friends from all around the globe during her travels.

Patagonia and Southeast Asia

Since the Colombia expedition, Debi has conquered Patagonia and Thailand, each destination offering unique challenges and experiences. For her, Patagonia was breathtakingly beautiful; while the extreme weather – gale-force wind gusts, rain, and cold – presented challenges, Debi enjoyed the long distances on meandering gravel roads in Argentina and Chile.

Grandmother Leaves Cruisers For Dual Sports To Ride The World

“I embraced the distances we covered in Argentina, although ‘long distance’ on a small dual sport bike is much different than ‘long distance’ on my comfy Road Glide! I consider this group of women and this trip in particular a boost to my skill set and frankly, a hardcore experience on twos!,”Debi shares.

Grandmother Leaves Cruisers For Dual Sports To Ride The World

Thailand, on the other hand, didn’t feel like the right fit due to the more difficult terrain and an unfortunate slide across a narrow, slippery mountain road that shook Debi’s confidence. “Before signing up for a tour abroad, always ask questions; it’s worth booking an extra day or two to familiarize yourself with a new bike and riding conditions too,” Debi advises.

Grandmother Leaves Cruisers For Dual Sports To Ride The World

Pack Light, Go Far

Debi’s next adventure will take her to the Himalayas in India, where she will be tackling the highest passes aboard a Royal Enfield. For Debi, women-only tours are her preferred choice of travel. “As for choosing a new country to explore – I need to see the world before my time on Earth is over, so choosing a destination is easy!” Debi shares.

For those considering adventure riding, regardless of age or level of experience, Debi’s message is clear: age is an attitude, not a number. She encourages women to talk to experienced riders, follow adventure enthusiasts on social media, and take a training course. Her workshops on transitioning from street to adventure riding have become a source of inspiration for women looking to embrace the thrill of off-road exploration.

Grandmother Leaves Cruisers For Dual Sports To Ride The World

“I didn’t arrive at my 65th birthday and exclaim ‘I think I’ll take up ADV riding!’ It doesn’t work that way for me. When I decided I wanted a new challenge, and adventure riding was calling, I just happened to be 65. I don’t ever want to limit myself by age. I spent many years chasing a career, then raising children. I embraced motorcycling with a passion, and now that I’m retired, I have the time and resources to pursue that passion with intensity as well as try new things,” Debi explains.

For women looking to experiment with adventure riding and international travel, Debi’s tips include packing light, respecting the local culture and fellow riders, and embracing the unknown with gusto.

“Ask questions. Pack anti-diarrhea meds. Don’t drink the water. Be considerate when sharing a hotel room. Buy a SIM card at the airport. Most importantly, embrace the dust, dirt, mud, and rain as if you were ten years old again!”

Grandmother Leaves Cruisers For Dual Sports To Ride The World

As Debi continues to break stereotypes and explore the world on her motorcycle, she serves as an inspiration for women of all ages to embrace their passions, challenge themselves, and live life to the fullest. Her story is a testament to the fact that the adventure of a lifetime can begin at any age.

Follow Debi on social media and her women’s motorcycle rallies presentations: @bessieandme

Author: Egle Gerulaityte

Riding around the world extra slowly and not taking it too seriously, Egle is always on the lookout for interesting stories. Editor of the Women ADV Riders magazine, she focuses on ordinary people doing extraordinary things and hopes to bring travel inspiration to all two-wheeled maniacs out there.

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