Jess Stone has spent more than a decade traveling the world by motorcycle, a journey that began when her husband Greg taught her to ride while they were working as aid workers in Liberia and later grew into multi-continent expeditions, the founding of RUFFLY dog gear, and their current around-the-world ride with her White Swiss Shepherd, Whimsy, raising funds for Girl Up. At Overland Expo SoCal in Costa Mesa, she will share stories and lessons from the road during her session “To the Far North and Extreme South with My K9 Co-Pilot” on Saturday, March 14 at 11 a.m. at the Oasis Bar and Food Court sponsored by Nokian Tyres, and again on Sunday, March 15 at 2 p.m. at the DIY Showcase Bivvy, where she and Greg Stone will present “Motorcycles, E-bikes, Snowmobiles, and More: What You Need to Know About Riding with Your Dog.”
Tell us about your rig(s)
I ride a custom-painted purple 2023 Triumph Tiger 900 Rally Pro. On the back, I have Whimsy’s K9 Moto Cockpit mounted so that she can ride the world with me! Greg also rides an identical Tiger 900 Rally Pro, but without the snazzy color or Cockpit on the back. He carries the camping equipment.
All-time favorite campsite?
Tuktoyaktuk, hands down. After riding the Dempster Highway all the way to the Arctic Ocean, we camped right on the shore of the Beaufort Sea under nearly 24 hours of daylight. Moxie, Greg, and I splashed around in the freezing ocean, and Greg celebrated with a well-earned cigar. After such a tough route, reaching a place we failed to reach 10 years before made it the perfect, unforgettable campsite.
What’s your go-to overlanding meal?
Lately, I’m on an Indian dal kick. It’s easy, comforting, and perfect after a long day of riding. Sometimes I even used canned lentils to speed it up even more. I pair it with either 5-minute rice, or sometimes I get fancy and create my own garlic naan. I love cooking from scratch, and camp cooking gives me an excuse to experiment, and when you’ve been riding all day and are absolutely starving, camp food always tastes incredible anyway!
Best silver-lining story?
I set off on our around-the-world adventure on a BMW G650GS that had a habit of leaking oil. We thought we’d finally solved the problem, but once we reached Mexico, it became clear the issue wasn’t done with us yet. On a Saturday morning in Lerma, we rolled into the BMW dealership hoping for a quick fix.
We had an event to meet with a Girl Up club in the city on Monday, so I needed my bike ready to go on Sunday at the latest. The service team assured us the leak was repaired and advised us to let it cure for a few hours. We waited as long as we could and left the dealership just as they were closing for the day.
I made it not 10 minutes from there when my bike started gushing oil all over the road. Luckily, we were on a surface street before getting on to the highway, and I was able to limp the bike into a nearby gas station. Greg and I looked the bike over while Moxie stayed calm in her Cockpit. As we were trying to figure out how we could either do a field repair or get the bike to a service shop to fix it, a group from a local Mexican motorcycle club pulled up, cuts on, and exactly as intimidating as you’d expect – until they introduced themselves with big smiles. One of their Harleys had broken down earlier, and they were stuck waiting for a tow truck of their own.
They welcomed us into their circle without hesitation. Someone handed me a bottle of artisan mezcal, and soon we were swapping stories, loving on Moxie, and collectively scratching our heads over the oil leak. No quick fix revealed itself, but the club didn’t leave us hanging. They insisted we use the tow truck they had already called first, offering to get my bike safely back to the dealership so it could be stored overnight.
I rode up front in the tow truck with the driver and Moxie – possibly after one mezcal too many – while Greg followed behind on his bike. It wasn’t how we planned to spend the evening, but it was a perfect reminder of why we love this life. No matter where you break down, the brotherhood of bikers runs deep, motorcycle club members and stranded travelers alike!
What is an area of overland travel that you think you have nailed?
I’ve become an expert at finding dog-friendly activities on the road, so we never have to leave our dog behind. I love tracking down unique experiences, whether it’s visiting a crocodile farm in Mexico (where you can buy one as a pet for $100 – but don’t worry, you trade it in for a baby when it gets too big), kayaking with your dog on Lake Atitlán in Guatemala, taking a boat tour to see penguins in Patagonia, or attending a goat-cheese workshop at a working goat farm in Mexico.
One thing Greg and I are still learning is how to plan shorter days. On paper, the distances always look manageable, but once you factor in rest stops, activities, and the reality of daylight hours, we often find ourselves setting up camp just before dark. It’s a good reminder to build in more breathing room—shorter routes mean more time to enjoy the ride, the experiences, and actually relax once we reach camp.
What does your “division” of labor look like while traveling?
I handle most of the logistics on the road, from planning routes and activities to organizing meals and campsites. Greg focuses on bike maintenance, filming, and managing our gigantic library of footage. Because we’re running RUFFLY while we travel, Greg also takes the lead on communicating with prospects and guiding customers through their Cockpit designs. I manage and create the content for our social channels, and together we remotely oversee our RUFFLY team based in Guatemala.
Meet Jess Stone and hear how she’s riding around the world with her dog Whimsy on the back of her motorcycle, be sure to come to Overland Expo SoCal, happening March 14–15 in Costa Mesa, California. Jess will share stories and lessons from years of international overlanding, building RUFFLY dog gear, and life on the road with her husband Greg. To learn more and purchase tickets, click the button below.
