WHEN I'D SIGNED UP for L'Eroica two months earlier, I had no idea what an all-day ride with extreme elevation changes entailed, but it had seemed the perfect challenge: to transform a middle-aged surfer/tennis player with declining mobility and a bad back into a far more resilient athlete, one who could, for instance, ride hard all day in the Chianti hill country. And it would all be for a good cause.

A dozen years ago, Giancarlo Brocci kicked off the tour to celebrate the strade bianchi and rally support for their preservation. Some, citing the dust and wear on their high-end roadsters, craved blacktop. Brocci and his fellows in the Parco Ciclistico del Chianti foresaw that asphalt would not only ruin the character of the countryside; it would also pave over a lot of the history of il grande ciclismo, the midcentury era of mud and blood that saw the rise of national heroes like the legendary Fausto Coppi, Il

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.

Campionissimo, "the Champion of Champions." The event they created is part costume ball, part battle reenactment, with a sawtooth profile resembling a mountain stage of the Tour de France. The first Eroica drew about 100 faithful, but last year's event attracted thousands of cyclists from more than a dozen countries, many of them riding beautiful antique bikes and kitted out with period gear and clothing. Lugged steel, wool jerseys, leather saddles, etc.—all of this is encouraged, but I also saw carbon-fiber frames and people wearing as much spandex as Spider-Man. With four courses to choose from—38, 75, 135, and 205 kilometers—you can randonnée through the Chianti well into your dotage.

Speaking of which, at age 53, and with zero road-bike experience, I might have chosen one of the shorter courses. But committing to an event far beyond my abilities was just the sort of psychological jump-start I needed. I was already following "a sensible program of exercise and diet," and it had me firmly mired in mediocrity. In tennis, for instance, all too often I heard myself saying "Too good" rather than pursuing an opponent's would-be winner as I'd once done, with the mad fury of a Jack Russell terrier.

I needed a bike. I soon found a well-preserved, Eroica-appropriate ten-speed: silver and maroon, with full Campagnolo, downtube shifters, a burnished leather Brooks saddle, and 30 years on her. I named her Lola after the swift and tireless heroine of the German cult film Run, Lola, Run. I'm six-one, 185 pounds; at 25 pounds, she's svelte for her age. We meshed biomechanically right from the start. She seemed to have an invisible motor, a get-up-and-git that made me want to ride and ride.

I soon contacted an Eroica veteran, San Francisco wheelman Bob Freitas, seeking advice. His response was terse: "My condolences." He added, "Florida ain't Tuscany" (I live in flat Tallahassee) and "Those elevations are in meters, not feet." My friends were even more skeptical. One, well-versed in the physiology of exercise and recovery, opined that 127 miles of hills would kill me outright. I feared an Italian bonk, and I feared an Italian sag wagon, just waiting to scrape my sorry bonked ass off the gravel, the way Irish peasants once feared the banshee's coach. I found the only hills in town and started putting in my miles.

By September I was clocking 50-mile loops, returning home broiled the color of steak tartare and having off-gassed surplus pounds into the atmosphere. I'd dropped nearly 20 of them, to 167, had a spring in my step, and had no more back troubles. Old and slow, maybe so, but I was hungry for that ghostly gravel.