“How many hellingen,” asked legendary Flemish folk singer Bob van Dylan, “must a man cycle up, before they call him a Belgian hard man?”

I had always thought it was a rhetorical question, but a few days before the Tour of Flanders sportive I print out Condor’s handy little cut-out guide and discover the answer is in fact 17. That's 17 steep, cobble-coated Belgian weapons-grade hills.

I sit by my computer mulling over the prospect of that many hills and cursing van Dylan for his obfuscatory lyrics. I have enough trouble with one hill, never mind 17. This is the kind of minor detail I should really look into before signing up for things like the Tour of Flanders, I think to myself.

Fast forward a few days: it’s 9am on the morning of the ride, and I’m in Belgium, held up in Kortrijk train station waiting for a connection to Oudenaarde where the medium distance sportive starts. I’m trying to focus on eating a baguette. It has a surprise ingredient, cabbage – not something I usually have for breakfast – and an elderly local has taken a shine to my bike; he is reeling off cyclists’ names at me in lieu of conversation. “Boonen-Van Avermaet-Sagan-Cancellara!” I smile and nod.

My girlfriend meanwhile, having miraculously agreed to drive over with me as soigneur, is still asleep in Bruges. Not for the first time I question her sanity, and that of non-cyclists in general. How could you prefer sleep to this? “Wiggins!” I reply to the old man. He wanders off in disgust.

Twenty minutes later the train deposits me, an hour behind schedule, in Oudenaarde. I’m worried about being late. Will there still be enough hills left for me? Three friendly Scots from my train, who’ve done the Flanders sportive before, point me to the nearby registration hall. I spot a sign for “Trouble Desk” and head towards it instinctively. Here I swap my full-length, 260km entry number for a more sane entry to the 134km route. There’s just time for a quick check of my route card – still 17 hills, great – and with that I’m set loose into the mystical cycling heartland of Flanders.

For those who aren’t familiar, the Tour of Flanders (or Ronde van Vlaanderen locally) is one of cycling’s five “Monuments”, the prestigious one-day races held each spring. Victory in one of these classics can transform entire careers. In other words, it’s Quite a Big Deal, and especially here in Flanders. The sportive takes place the day before the pros race the same route, and already the locals are out in force along the roadsides, rehearsing their cheering and drinking ahead of the main event tomorrow.

I decide as I clip in and roll over the start line that my main ambition for the day is not to fall off my bike in front of a crowd of tipsy Flemish cycling fans. Anything else is a bonus.

Rolling along the opening few km, all is well. The morning is a little overcast but brightening up – and a few hours later we’ll be basking in beautiful sunshine. My spirits lift. So where are these hills?

I am halfway up a gentle incline when I check my Garmin and suddenly realise I’m on the Wolvenberg – hill number one! It’s tarmac not cobbles, so has taken me by surprise. I click down the gears, stand on the pedals and prepare to spin, only for the road to promptly flatten out. Is that it? I ride on, feeling disdain for what passes for a hill in Belgium. That was all over in two minutes, I think to myself. I’ve had tougher workouts lifting our cats off the garden wall.

My smug reverie is suddenly shattered by violent turbulence beneath my wheels and a sensation of extreme vibrationary discomfort in my hands. And arms. And legs. And undercarriage. My first thought is that a sniper has shot out my tyres; I duck low on the bike and try to hurry on. Then I realise it’s worse than snipers: I’m on cobbles, and all the horror stories were true.

This is very unpleasant indeed, I think to myself as my bike appears to implode noisily beneath me. After just 800m the Ruiterstraat, as this section of kasseien (cobbles) is called, comes to a merciful end and I’m back on civilised road again. I give my poor bike a reassuring pat, but in my head I’m making funeral arrangements: she’ll never survive this beating.

By the time the next stretch, Kerkgate, comes along a few minutes later I have formulated a cunning plan to save me and my bike from unnecessary suffering. As the cobbles begin I make a beeline for the narrow but relatively smooth concrete gutter along the side of the street, and stick to it. Sometimes parked cars mean I have to venture onto the cobbles, but where possible I hop into the gutter to avoid the bone-rattling stones. I reach the end of the 2.6km section feeling guilty but vindicated, like a shipwreck survivor who has had to eat his fellow crew to survive.

‘I’ll do it again if I have to,” I vow grimly as I latch onto the wheel of some meaty-looking and unsuspecting fellow riders.

“Alright Brighton!” one of them greets me and my giveaway jersey as I pull up alongside. It turns out he’s come from Gloucestershire via Wimbledon, and just like Chaucer’s pilgrim he has a Flanders tale to tell.

“My tyre shredded 10 minutes in,” he explains, “totally ruined. So I pull over into the driveway of a house thinking that’s it, my day’s done.

“Then the guy who owns the house comes out and asks what’s happened. Next thing I know he’s driving me to a bike shop six miles away to get a new tyre!”

On we ride, the cockles of our hearts aglow at this example of Flandrian hospitality. And still the hills and the cobbles keep coming. Names laden with resonance like Molenberg, Koppenberg, and er… Karnemelkbeekstraat arrive and are conquered, each climb proceeded by a handy sign setting out the name, length and gradient we are about to endure.

But the funny thing is that although these hills are steep, the roads are narrow and the cobbles are the gnarly stone gonads of Satan himself, I find myself actually looking forward to them. They give the ride a focal point, and weaving and bobbing up each short climb amid the encouraging cheers of roadside supporters is a surreal delight. On the Koppenberg I even find a burst of energy and a space ahead of me to pass the file of dismounted warriors wheeling their steeds to the top, only to be overtaken – the indignity! – by a chap insouciantly riding a bakefiets.

The 80 miles roll by in a happy albeit occasionally bumpy blur, with a few timely breaks to refuel on water and caramel waffles. The sun is out, it feels like a festival, but all too soon the last climb – the Paterberg – is upon us. With an average gradient of 12.9% I guess it’s not called “the daddy” for nothing, but a short sweat out of the saddle and it’s all over in a few minutes, leaving a flat blast to the finish 10km away in Oudenaarde.

I get back to Bruges tired and triumphant to find my soigneur has been sunbathing and taking snapshots of the FDJ team, who have seemingly got lost in the town centre on a reconnaissance ride. The next day we’ll drive down to Oudenaarde again to watch the pros tackle the race at warp speed, but for tonight it’s off to sample some of Belgium’s other delights in the form of frites, steak and strong beer. All I can say is, get yourself to Flanders next year and ride this for yourself – it’s an experience like no other, and my new favourite sportive.