Here is a cherished childhood memory: the thrill of watching Steve McQueen riding an Enfield Bullet in the closing scenes of The Great Escape. The panache with which he jumped all those wire fences lingered well into adult life, and survived even the realisation that a friend of McQueen’s, Bud Ekins, was at the helm of the bike for the most formidable of the stunts. No matter. The association of motorcycling with freedom was etched permanently in the mind.

Nigel Winter, an associate specialising in family law at Sussex firm Rawlison Butler, is a man who goes one step further than simply endorsing the image: he lives the life, too. A devotion to motorcycling spanning two decades is about to see him set off from Land’s End to John O’Groats by way of the recreation – for the first time – of one of the most famous episodes in the history of motorcycling. Winter will be following the “Gaffers’ Gallop,” the route taken by three “gaffers” of the Triumph factory in 1953.

“Plenty of people have travelled from Land’s End to John O’Groats in all kinds of ways,” says Winter. “But no one has retraced the steps of Edward Turner, the man who built and owned the Triumph factory. He set off with his works director and his service manager to prove a point: that the marque’s smallest bike was completely reliable.”

Winter explains: “Turner’s 149cc motorcycle covered 1008 miles in 27 hours and 29 minutes at an average speed of 36.68 mph, returning 108 mpg while carrying a rider of 14 stones and 3 pounds. He made it to John O’Groats via Exeter, Honiton, Shepton Mallet, Bath, Cirencester, Stow On The Wold, Leicester, Doncaster, Scotch Corner, Penrith, Carlisle, Lanark, Stirling, Perth, Pitlochry and Kinguisse. The country today looks very different, both topographically and economically. But there is one great constant: Triumph Motorcycles.”

As well being the proud owner of an Enfield Bullet, Winter owns two Triumph Thunderbird bikes, one of which he will ride on the Gallop. He aims to cover an average of 200 miles a day for a week, but his methodology will allow for plenty of detours. “One of the joys of riding a motorbike is getting out onto a country lane, winding back the throttle and just going wherever the mood takes you,” he says. This, indeed, was his favourite way of relaxing when studying for his Law Society Finals.

Winter cites Ted Simon’s cult book Jupiter’s Travels as one of his inspirations. “Ted Simon completed a world tour in 1973 on a Triumph 500. What was wonderful about it is that he put the bike on the ferry to Calais and simply turned left when he got there. He had no idea where he’d go and this is one of the great things about motorcycling – you have this amazing piece of equipment that for very little cost can take you round the world.”

The freedom from biking comes not just from getting off the beaten track. For Winter – and, he says, many other lawyers – there is a pleasure in the bikers’ anonymity. “You don a leather jacket, a pair of old jeans and a helmet and turn up among other bikers, and no one knows you’re a lawyer. I enjoy my profession immensely but there is something gratifying about downing tools and mingling without one’s job being definitive of one’s personality. Funnily enough, when I get talking to them, a lot of the people I meet in their leathers are also lawyers.”

Winter’s brethren, whether of the leathered variety or the more conventional suited kind, will admire the ultimate purpose of his Gallop – to raise funds for cancer research. Along the way, with his tent strapped to the back of his Triumph 900, Winter will enjoy meandering among the lanes of the British countryside, sampling “a Britain from the 1950s that still exists, a place where real ale is still served from micro breweries with food that hasn’t seen a sell-by date or roll of cling-film”.

Whatever happens, Winter will not be lost, for as he put it to his wife Tracy when on their honeymoon (on a motorbike): “I’m not lost – I just don’t want to be found.”

Nigel Winter’s Gaffers’ Gallop for cancer research starts at the end of June. For more information see www.gaffersgallop.com

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