He ran Hamilton's Around the Bay and won't stop until he finishes the Boston Marathon

Jim Willett ran Around the Bay in Hamilton 11 days ago and hasn't stopped since.

Of course, he's taken breaks to sleep and inhale calories, but rather than staggering off to rest and reconsider his life choices, he finished then set his sights on Massachusetts.

The plan is to run 875 km from the starting line of oldest road race in North America to the finish line of the second oldest — the Boston Marathon.

For Willett to meet his goal he'll have to maintain a punishing pace of about 60 kilometres —roughly a marathon and a half — each day.

Typically, the first question he gets is why?

The 45-year-old doesn't have a single answer.

"Runners really appreciate and get it more so than people who aren't runners … but even most runners think it's a little bit far," he said with a laugh.

Years ago, after surviving cancer, Willett started running ultra marathons, which he describes as grand "adventures."

But this time around he didn't want to just run for himself. Instead, he wanted to run for a cause.

Willett is known around the running circuit for having a "pretty impressive sock game." His flashy footwear is something of a calling card, along with the collared shirts he wears during races to remind himself not to take them too seriously.

Online research led him to read about how socks are often the most commonly requested items at homeless shelters.

That need, coupled with his appreciation for durable footwear and personal experience growing up relying on social assistance programs and times without a roof over his head made it clear what he should be running for.

"It felt like a natural fit," he quipped.

So far, the Newmarket, Ont. runner has raised more than $6,400 for durable, good-quality socks that will be distributed at shelters across Canada. And he isn't slowing down.

Every step is a decision to move forward

On Wednesday, fuelled by nuts, bread and sometimes even candy, he crossed the 600-kilometre mark.

Along the way he and his friend Don, whose recumbent bike acts as the pair's pack mule, have startled horses, been ignored by groundhogs, chased by dogs and drawn plenty of puzzled looks by passersby — including a U.S. border guard who, when told why they were crossing into New York, responded with "Well, that's a new one."

But those unique moments and experiences that you get by covering ground on foot, instead of in a vehicle, are what keep Willett going.

"Really it comes down to moments in the day," he explained. "Running is such a simple thing and every step that you take forward is literally another decision you make to move forward so there's really two options — you can stop or you can go —it's simple but it's powerful."

It's an unexpected journey for a guy who said he was "never much of a marathon person."

Instead of the crowds and commotion of your typical race day he prefers to run through the wild in the kind of places where "you're just a speck on the landscapre."

Making the Boston Marathon an adventure

The trip to Boston is a long trek, but Willett has previously run a marathon in New Brunswick before jogging to Ottawa to complete another one there, so he has experience, but this one is a little different.

The Boston Marathon is the holy grail for many runners and Willett said he's never heard of anyone running there before.

"I thought if I'm going to do Boston I'm going to turn it into my own adventure," he explained, adding he expects once he arrives and finds himself surrounded by thousands of runners and spectators he'll get caught up in all the excitement and energy.

Willett is already past the halfway-point and said his body is starting to feel the distance. But soreness is something he's come to accept and overcome.

"There's a fine line between stubborn and persistent and I think I've spent a lot of my life sort of straddling that line," he said.

Still, even Willett has his limits. It's not likely he'll take on almost 900 kilometres again.

"This is probably a one and done for me," he said with a laugh.