This year the group completed their longest march yet, from Kilmarnock - venue of their final away fixture in the Scottish Premier League (SPL) - to Inverness for the last home game.
The marchers completed an overnight, 82-km first leg and three of them covered the whole distance - 305 kms in six days.
Over the years the group have passed through urban tunnels, muddy bogs and spectacular gorges but there have been only two ever-present participants: Englishmen Steve Taylor, 56, and 25-year-old Robert Wilson.
The idea, Taylor's brainchild, was born on New Year's Eve 2002 in an Inverness bar.
"I said to the guys: 'I'm going to be 50 next year and I fancy doing something to celebrate it'," he told Reuters by telephone a few weeks before setting off on HM7.
"We tossed a few ideas around, then I said: 'How about we walk to the last game of the season?'
"We weren't actually going to do it again, it was just meant to be a one-off. But the following year, once we got into the deepest part of winter, a couple of the boys who had done it said: 'Why don't we just do it again?'"
This steely attitude and sense of adventure is one of the reasons the march has endured so long. Another reason is the extraordinary Taylor.
FELL RUNNING
Born and raised near his boyhood club West Bromwich Albion on the outskirts of Birmingham, Taylor developed strong legs and a never-say-die resolve by fell running.
So it came as no surprise when he decided to run 100 miles (161 kms) in less than 24 hours to mark his 30th birthday.
"Something went bang in my knee at 71 miles, but because the guy in second was catching me I had to keep going," he told Reuters minutes after setting off on the penultimate day of HM7.
"I eventually managed 102 miles, after 22 hours straight, and although my knee was problematic at the time I was back racing on the hills five weeks later."
For his 40th it was a 237-mile (381-km) route from Manchester to Glasgow in a day with a group of workmates, thankfully this time on bikes.
"I lost concentration after 70 miles, fell off my bike following a drink stop and broke my elbow. I'd told everyone at work I'd finish it so I just got back on and cycled the rest one-and-a-bit-handed," said Taylor, who works in information technology.
"It wasn't exactly the Tour de France but then we were just a bunch of working blokes from a factory."
Taylor's spirit has clearly permeated all the participants of the march.
"If Steve wasn't here it just wouldn't be the same," said Wilson, who despite wearing a heavy kilt sprinted to a meeting point on the 32-km penultimate day of HM7 just to beat others in the group.
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