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Before you read any further, buy some padded shorts. Because if you fancy a weekend spinning along 50 miles of stunning East Hampshire countryside, you’re going to need them. Besides that, no experience is necessary to ride the Shipwrights Way, Hampshire’s new 50-mile path, which opens officially next week. I made it (despite the unpadded agony) — and my cycling experience is limited to drunken Boris Bike wobbles and that spin class I accidentally took last year.

Part of Cycle Southern England’s new initiative to get more of us pale, wheezing city dwellers into the countryside, the Shipwrights Way runs from Alice Holt Forest, south of Farnham, over the South Downs and all the way to the sea, finishing at Portsmouth Historic Dockyard. It’s named to reflect the journey of oak from forest to docks during ye olde times of medieval shipbuilding.

An hour’s train ride from Waterloo gets my friend Charlie and me to Bentley, our starting point. Adam and Ben of Alice Holt Cycle Centre meet us with our bikes, as they do for all amateurs without their own wheels.

After a wobbly test cycle around the car park, I strap on my helmet (“That helmet’s on backwards, by the way,” Adam points out) and we set off, through a beautiful dappled wood that is forgivingly flat — for the first 100 metres, anyway.

Still, the incline’s not too bad, and the vegetal energy exuded by all this nature malarkey carries me through. After two miles we complete section one and arrive at the Cycle Centre in Alice Holt Forest, in time for a cup of tea. Chris Froome, eat your heart out.

Section two sweeps right through the forest. I cackle wildly as we shoot down pebble-strewn paths like a free-wheeling witch. The air feels easier to breathe, my surroundings brighter and more sharply defined than London. And in Bordon, there’s sheep, baaaing and gamboling as if on cue for jaded city types. “It’s just so NICE to get out of London!” I think to myself, like a wide-eyed prisoner on day release.

Leaving the forest, there’s a three-mile stint through residential streets in Bordon and Liss, totally devoid of cars and speed-walking commuters. Lunch options are sparse without going significantly off-route, with little on offer besides a massive 24-hour Tesco and a tyre shop. The saving grace is the Old Dairy Café. Its simple plastic tables and laminated menus belie the giant, fresh doorstop sandwiches within. It’s precisely the kind of comforting stodge needed after three hours of cycling.

Half a mile up the road and faced with a slight incline, we decide it’s pub time. The Woodlark might be a slightly sticky chain pub but the first sip of creamy, Marmitey bitter brings tears to the eyes. Or maybe it’s the thought of re-saddling. Because by this point, seven miles of bumpy, off-road cycling wearing thin, unpadded shorts is starting to smart. It’s with gritted teeth, a fair amount of swearing and a strong desire for more pain-numbing booze that I remount.

Relief comes sooner than expected when I get a puncture in Blackmoor. Luckily Alice Holt are on-call for idiots who don’t think to bring a puncture kit: within 20 minutes Ben has arrived, fixed my bike and cheered us on our bum-numbing way again.

Everything’s fine until we reach Petersfield, home for the night. Only 100 metres from No1 The Spain, our B&B, I manage to fling myself into the road. Millennial instincts mean breaking my fall with an elbow rather than risk damaging my iPhone. Result: one bloody elbow, one unharmed phone. Worth it. Plasters and antiseptic from the lovely woman who runs the B&B help. The best medicine, however, is that of the whacking great gin and tonic at The Old Drum, a stunning restored 18th-century pub in Petersfield, which has 20 gins behind the bar. By the time I’ve made my way through a bowlful of mussels, a beautifully cooked bit of gurnard and a hefty cheese board, the 30 miles ahead tomorrow seem a long way off.

Reality hits the next day over a full English — my bum really aches. Still, sections seven to 11 are flatter than the previous day which, theoretically, means fewer breaks from which it’s so violently painful to remount. The hardest part of day two comes first: a near vertical hill by a chalk pit, leading into more vertical ups and downs in Queen Elizabeth Country Park. At least, it seemed vertical to me — if not to the small children effortlessly overtaking.

After a short, diabolical stint in the park, there’s a joyously fast flat stretch streaming along country roads, and we’re in Finchdean by 11am. Buoyed up and already keen for lunch, we whizz on towards Havant, arriving dead on 12.30pm outside a gastropub. The name of the pub, The Wheelwright’s Arms, seems to be deliberate mockery — my bum knows there’s nothing remotely right about being on two wheels right now. But a pint of local Upham Brewery ale and fish and chips in the sunny courtyard imparts sufficient booze haze to get back upon that infernal saddle.

The usual ferry for the last leg isn’t running, meaning we have to slog the last 10 miles around a boggy estuary to Portsmouth. But finally, we’re there. And to the joyfully hipster Southsea Coffee Co for a Hoxton-worthy flat white and fabulous salted caramel slice. From there it’s just a gentle five-minute spin to Portsmouth Harbour station for a direct train back to London, where a soothing bath awaits my knackered behind. Although not before a celebration photo underneath a deeply appropriate street sign leading to the station: Victory Road.

Details: Hampshire

Cycle Southern England (cyclesouthernengland.co.uk) has downloadable maps detailing shorter routes on the Shipwrights Way as well as the whole trail.

Alice Holt Cycle Centre (leisurecentre.com/AliceHolt) offers bike hire starting at £25 per day or £45 per weekend.

No1 The Spain (1thespain.com) offers B&B accommodation starting at £80 per double or £50 for a single.

visit-hampshire.co.uk