After the brutal climb to the village of Radda, with only ten kilometers to go, I was about to bonk, nary a revolution left in my legs. Then I heard the cheers from the crowd: mama, papa, and daughter in kneesocks. "Bravo!" they shouted. I nearly burst into sobs of gratitude. Of the roughly 3,000 riders in Italy's 12^th annual Eroica, an epic, old-fashioned cycling tour up and down the hills of Tuscany's Chianti region, I must've been nearly last. All well-wishers had abandoned their posts save these three, the patron saints of slowpokes.

My spirits soared.

And then I was plummeting down yet another motherfucking gravel hill. I foolishly hoped it might be the last in the 205-kilometer route I was following in skinny-tire travail. Over the rural strade bianche, or "white roads" of shale and limestone, the dying October sun cast magic-lantern shadows from behind a stately colonnade of cypress trees. That and the violent drubbing of my tires over the white washboard nearly strobed me senseless. Yet here on the other side of exhaustion, a mere floating head of witness, I instinctively, effortlessly dodged potholes and washouts at a speed that would surely have wrecked me earlier. Then the road flattened out through a good long stretch of plowed and fragrant farmland, and I thought, for the hundredth time, Che bella!—and, there being no other riders in sight, that I'd missed a sign.

I stopped and rotated my torso to look back, my neck being no longer operable. A-ha! Here came some other poor bastards, on venerable old bikes like mine, rattling down the hill. I wasn't last, or lost, after all. I set to it again, spinning a favorite, honey-smooth middle gear. "Piano, piano," I said, gently coaxing the lugged-steel bones of Lola, my dauntless 1978 Trek, and echoing the signore at the previous night's Heroes' Feast. In the host village of Gaiole in Chianti, my glass had been kept brimming with Chianti Classico as we roared and toasted all things ciclismo. At my table, a local coach had offered a strategy for the next day, making gentle pedaling motions with his hands: "Piano, piano..."

That is, "Slowly, slowly..." Easy does it.

But now it was starting to look as if easy wasn't going to do it after all. Nearly 14 hours of grinding up and banging down steep gravel had taken its toll on my Lola: a spoke sproinged; derailleurs in dire need of adjustment; wheels out of true; taillight long gone, rattled clean out of its bracket. But she was still the belle of the brawl to me. Her lightweight American steel had absorbed countless bone-rattling blows on my behalf and kept on rolling, past many a mechanical breakdown. As for me, I'd had my brains knocked out of true. Like a visionary in the desert, I was running on soul.

Night crept from behind distant purple vineyards. A brief steep climb and then the strade bianche T'd into tarmac, the sudden ease like a jolt of espresso. Cars whiffed by, lights on. A van slowed—my tablemates from the feast. Done, celebrated, and heading home, they shouted "Almost there!" and left me to my pain. So the long-dreamed-of finish line in Gaiole's cobblestone piazza was close. I looked and thought I could see the hilltop village's lights blooming down below, but the route swung away, back into forest.

Darkness. I toggled Lola's headlight. Dead.

L'Eroica, it should be noted, is not a race but a randonnée, a road trip for the pleasure of the ride. Still, it's a point of considerable pride to finish the longest route within the "heroic" time frame of 5 A.M. to 7 P.M. That deadline was minutes away.

As I flew downhill through a landscape like a vast black-on-black Rothko canvas, I glimpsed below me the red taillight trails of three riders streaking for Gaiole and glory. If I could catch them, I might beat the deadline on borrowed light.