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Glue. Gravel. 28mm hand-sewn tires. Downtube shifters. Squealing brakes, that perfectly pitch-black nothingness that you only find right before dawn, still draped over the Italian countryside, is being pulled back slowly by the coming day. An old, thick chain elicits a rich, rhythmic rattle from the yellowed steel of a Regina. A lot’s changed since it was new. You can almost count the teeth while it spins. You’re over-geared, and perhaps a little over-excited. Don’t worry. There’s only 200km to go.

That opening stretch comes and goes in a fog of anticipation and trepidation. With sparse light and sparser company, friends call to one another out in the empty, inky darkness and except for scattered replies and whirling freewheels, the roads are silent. It’s all a blur, like the tarmac racing past under wheel.

On any other day the weathered and crumbling stonework and the grand old gates of the Castello di Brolio would be a welcome site. It’s a fine property that makes finer wine and past the walls and the woods that surround it, the vineyard gives way to the Tuscan countryside in all it’s glory – rolling swathes of ochre and olive and green as far as the eye can see. On any other day, you might stop for a picture.

Not now. Tiny flames flicker and light the route through the still-black Brolio, up the cypress-lined ascent away from the familiar comfort of tarmac and up towards the dusty, uneven, ragged hell of the gravel. The Strade Bianche. What you came for. What you thought you were ready for.

Loose dirt and the scars cut deep through the grit by heavy rains mean that the strade are never easy. Even when they’re flat, they’re testing, coaxing you to go faster than you should. Inviting a puncture. Begging you to put a wheel wrong. And when they go up? Chianti’s hills are far from the malicious extremes of the north, but farther still from benign. Climb up a 15% stretch of uneven gravel on an antique with no compact and you’ll know all about it.

It ain’t all bad though. The highs are sweeter than the lows are sour and just when you’re almost broken, the road relents. A stretch of tarmac, perhaps, or a rest stop. Wine. Cakes. Coffee. Ribollita. There’s some grappa under the counter if you’ve really had a hard time.

Those moments spent on the grass, or stretched out on a low stone wall beneath the gentle warmth of October’s afternoon sun, will last a lifetime. The rose tint of hindsight will take care of the rest. After the finish line, the struggle will seem heroic. After a day or two, it will even seem … fun. This sport’s hilarious like that, in a peculiar, twisted way. Not everyone’s idea of amusement, perhaps, but if you’re into it there’s nothing better. Samuel Beckett called it dianoetic. It was the laugh of laughs to him, saluting what he thought was the highest joke: Suffering. He’d have made a good cyclist.

Colin O’Brien is a freelance cycling journalist based in Rome, Italy. He was invited to come on an inGamba trip once, and never left. He can now usually be found staring at blank pages in Borgolecchi. 

Me and Jay

Colin O'Brien

Colin is an author and journalist from Ireland. He first met inGamba's founder João Correia back in 2013. João handed him a bidon full of Chianti Classico and took him to a three-course lunch. They've been friends ever since.