Meet the 92-year-old who realised her Route 66 dreams

The Mother Road is on many a biker’s bucket list, and this determined rider proved it’s never too late to make that dream happen

For most riders, Route 66 is the ultimate dream – a legendary stretch of asphalt steeped in Americana, freedom and the roar of V-Twins. For Jean Scott, that dream came true this summer in the most extraordinary way. At 92 years old, Jean swapped Somerset in the UK for the California coast, riding pillion on a Harley-Davidson^® Road Glide^® for 2,700 miles along the Mother Road.

It all started with a simple email. Jean reached out to Orange & Black Motorcycle Tours in Hampshire, UK, with a request they hear often: “I’d like to ride Route 66.” But then came the twist. Jean didn’t want to ride her own bike; she wanted to experience the journey as a pillion. And then came the kicker: Jean was 92 and she wanted to use the trip to raise funds for Dorset and Somerset Air Ambulance.

“When we heard her story, we knew we had to make it happen,” says Dave Marsh, sales and operations manager at Orange & Black. “We pride ourselves on helping customers create their dream trip, and Jean is a great reminder that it’s never too late to make those dreams a reality.”

Embracing the open road
It was June 2025 when Jean touched down in Chicago, ready to take on the adventure of a lifetime. Her guide for the journey? None other than Gary “Bear” Fleshman, Orange & Black’s legendary Route 66 expert. Bear welcomed Jean onto the back of his Harley-Davidson Road Glide, and together they set off west, chasing the sun toward Santa Monica.

“We don’t usually offer pillion-only rides,” Bear admits, “but we’re all for people finding their freedom through riding, and we wanted to help Jean experience that after she got the bug in her youth. Next year Route 66 celebrates its centennial, so we thought it only fitting that Jean come along for the ride and get a jump on hitting her own centennial milestones.”

Over 13 days, Jean and Bear covered eight states, battling all kinds of weather and ticking off some of Route 66’s most iconic sights: the Blue Whale of Catoosa, the Route 66 Museum and the Grand Canyon. “The whole experience has been full of highlights,” Jean says. “I think my favourite places to visit have been Kansas and Oklahoma as I’ve heard a lot about them but had never been before; and the Grand Canyon – that was breathtaking.”

By the time they rolled into Santa Monica, Jean had not only conquered the Mother Road but also raised awareness for a cause close to her heart. Dorset and Somerset Air Ambulance provides vital emergency services for local communities and is part of a network of 21 UK air ambulance charities that collectively undertake more than 126 lifesaving missions a day. For Jean, this ride wasn’t just about ticking off a bucket list, it was about giving back. The end of the tour was bittersweet – the conclusion of the adventure of a lifetime but also an incredible gift: Bear presented Jean with a leather cut, complete with badges commemorating her epic journey. It’s a piece of biker heritage she now treasures.

A hero’s welcome
Jean’s story didn’t end when the kickstands went down in California. Back home in Somerset, her local Harley Owners Group^® chapter embraced her as one of their own. At a recent Bridgwater H.O.G. meeting, Jean’s friend John Rodger, who plays in a ukulele band with her, gave a presentation about the trip and the chapter even gifted Jean a crash helmet and offered to take her on future ride-outs.

“A few years ago, Jean told me that she fancied having a ride on the back of a Harley. I kept it in the back of my mind, but didn’t take it too seriously – so I was surprised when she told me she’d booked with a specialist travel company to do Route 66 at the ago of 92!” says John. “Well, she made it out and back and thoroughly enjoyed the trip – and can’t wait to do another.”

Jean’s adventure is a powerful reminder of what the Harley-Davidson spirit is all about: freedom, community and the open road. For Jean, the message is simple: “It’s never too late to take that life-changing trip.”