As he approaches his 80th birthday, Dean Bingham, founder of Dean’s Sweets, isn’t slowing down. Instead, he’s gearing up for his next goal: a cross-country bike ride from the Pacific to the Atlantic, an ocean-to-ocean journey fueled by grit, curiosity, and purpose. “I think it’s a challenge,” he says simply. “There’s something pretty great about doing something that everybody else thinks you’re crazy for.”
For Bingham, cycling has been a quiet throughline stretching back decades. He first got on a bike as a kid delivering newspapers, then returned to it in his early career as an architect, commuting through Boston traffic because it was, as he puts it, “a heck of a lot quicker and easier, even when the weather wasn’t great.” What began as practicality evolved into passion, then into a vehicle for connection. Bingham joined his first ride benefiting the National Multiple Sclerosis Society 35 years ago, inspired in part by his father’s roommate, who lived with MS.
Since then, Bingham has marked milestones not with rest, but with bigger rides, including a cross-country journey in 2001, another in 2017, and the East Coast Greenway for his 30th MS ride. Each one has been layered with personal meaning and, increasingly, public impact. “It gives me an added incentive, an added goal,” he says of the fundraising component. “I like the idea that this is something I can do to help other people.”
This upcoming ride may be his most ambitious yet. Starting on the Oregon coast, Bingham plans to pedal thousands of miles east, raising funds and awareness along the way. There’s even talk of a record attempt through the World Ultra Cycling Association, though he’s quick to downplay it. The real goal, as always, is forward motion.
Bingham is the first to admit that the stakes feel different now. “It feels a little more of a challenge because suddenly I’m ten years older,” he says. “The years seem to make more difference than they used to.” This reality doesn’t give him pause, it just changes his rhythm.
A typical day on the road, he explains, is less romantic than one might imagine. “I look at a riding day as being a work day,” he says. “You spend six or eight hours on the road, take breaks when necessary, and then do it all over again.” Nights are spent in modest hotels (what cyclists call a “credit card tour”), eliminating the need for camping gear in favor of simplicity and a good night’s sleep.
Packing, too, has become an exercise in restraint. On his first cross-country ride, Bingham quickly realized he’d overpacked, ditching nearly ten pounds of gear within the first few miles. “I have no recollection of what I left behind,” he says, laughing, “but I just know that there was quite a lot.” Now, his setup is pared down to essentials: a seat bag, a small handlebar bag, and layers for unpredictable weather.
And then there’s the mental side—the long, quiet hours alone with the road. Unlike many riders, Bingham doesn’t fill the silence with music or podcasts. It’s partly practical, because he needs to hear approaching traffic, but it’s also a kind of discipline. “I think for me the physical [challenge is harder],” he says. “Mental…not so much.”
That doesn’t mean there aren’t moments of doubt. He recalls passing an airport access road on an early ride and imagining how easy it would be to stop. “You could be home in four hours,” he remembers thinking. Instead, he kept going. That decision, again and again, is the real work. For Bingham, endurance isn’t about proving something to others so much as continuing to show up for himself.
In Portland, he’s known for chocolate, but on the road, things are simpler: a route to follow and a goal to meet. At the end of the day, that’s what keeps him going. Not just the miles, or even the challenge itself, but the sense that the effort matters. “I like the idea that this is something I can do to help other people,” he says.
When this ride is over, he’s not thinking too far ahead. There’s no grand plan for what comes next—just the understanding that as long as he’s able, he’ll keep riding.
“I think it’s a challenge. There’s something pretty great about doing something that everybody else thinks you’re crazy for.”