Imagine spending five hours driving in circles around a single roundabout—all for charity. Sounds crazy, right? But that’s exactly what Jay Roberts and his co-driver Jake Dwinell did, and they only got pulled over twice. This isn’t your typical Cannonball Run adventure; it’s the polar opposite. Instead of racing across the country at breakneck speeds, these guys aimed to drive for the longest time while covering the shortest distance. And this is the part most people miss: they did it all to honor a legend and raise money for Alzheimer’s research. But here’s where it gets controversial—was it a pointless stunt, or a brilliant way to draw attention to a good cause? Let’s dive in.
A month ago, I shared Jay’s story about setting a record for a semi-autonomous cross-country trip in his 2017 Toyota Prius. But this time, he took on a challenge that was equal parts absurd and inspiring. Jay texted me, ‘On Saturday morning, I set a new world record—the most time spent driving in a single roundabout.’ The previous record? 4 hours and 28 minutes. Jay and Jake crushed it with 5 hours and 3 minutes. But why? Because, as any Cannonballer will tell you, they could.
It all started in a group chat with fellow enthusiasts. Jake stumbled upon a news story about someone setting a roundabout driving record, and the group saw it as an opportunity. ‘Low-hanging fruit,’ Jay called it. So, on October 11, they headed to a single-lane roundabout in Trumbull, Connecticut, to make history. Their goal? Honor Brock Yates’ first Cannonball Run in 1971 and raise $500 for the Brock Yates Memorial Fund. Spoiler alert: they raised over $1,118—and they’re still accepting donations (https://www.gofundme.com/f/going-dizzy-for-brock).
But it wasn’t all smooth sailing—or should I say, circling? Jake admitted, ‘This was way harder than I expected. The centrifugal force glued you in the seat.’ Unlike a Cannonball Run, where you can cruise for miles on autopilot, this required constant alertness. Every 15-second lap demanded focus, especially with other drivers who didn’t quite understand roundabouts. ‘We were judging how some people really know how to use roundabouts, and others just don’t,’ Jake said. By the end, they were barely crawling, yet some drivers still refused to merge.
And then there were the police encounters. Legally, they weren’t breaking any laws, which is ironic for Cannonballers known for speeding. The first officer rolled his eyes and let them continue after they explained their charity mission. But the second encounter almost derailed their record—until their friend Spencer intervened. ‘I was going to take one for the team if I had to,’ Spencer said, ready to distract the officer. Thankfully, it didn’t come to that, and the officer ended up laughing and taking selfies with them.
Jay calls their Prius the ‘Gonzo Prius,’ and it performed flawlessly—except for a massive puddle of air conditioning condensation under the car. When asked if it was worth it, Jay admitted, ‘This ranks in the single digits of the stupidest thing I’ve ever done in a car.’ But with a good cause and a record on the line, they made it work. After five hours of circling, the first thing they did? ‘Both of us had to pee so bad. Our kidneys were about to explode.’
So, here’s the question: Was this a pointless stunt, or a clever way to raise awareness and funds? Let us know in the comments. And if you’ve got a tip for our next story, send it to tips@thedrive.com. Because whether it’s a Cannonball Run or a roundabout record, there’s always a story worth telling.
