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I was just outside Gaiole in Chianti when the bolt holding the seatpost came loose. I wouldn’t be able to use the saddle anymore, but it didn’t matter. It was dark, and with nothing but a short-sleeve wool jersey, October’s bitter cold was biting. Keep the legs moving, I thought, and focus on that finish line.

Only 133 kilometers to go.

It’s funny how eager anticipation can blind you to the troubles ahead, and how hindsight rose-tints even the excruciating rides. Before leaving Rome with friends on the two-hour drive to Chianti, I was more than excited. L’Eroica is perhaps the world’s greatest classic bike race, and I was going to ride it. My thoughts were of rolling Tuscan hills, the thousands of like-minded people and all of the gorgeous vintage steel that such a gathering promises. And wine; plenty of wine. Back in the Eternal City, my memories are of much the same, with some fond recollections of friends met thrown into the bargain. But in between expectation and reflection, lay pain and suffering.

The riders tackling the 135 km and 205 km routes (there are 38 km and 75 km options too) can leave anytime between 5 am and 7 am, just before sunrise. Few make it back before dusk.

Setting off in that pure darkness preceding dawn, I was eager to start strong. With no lights and only the odd rider for company, those first few magical kilometers of L’Eroica were dark and almost silent; a magical blur, like the rushing pavement under wheel when you’re going full tilt. I’d been looking forward to this all year, and now that it was upon me, I was ecstatic. Maybe a little too ecstatic.

If you passed or were passed by me on those prefatory stretches, no doubt you’ll remember a young man on an old Bianchi, more resem-