When I blew a tire on the road between Vagliagli and Castellina in Chianti I thought for sure my day was over. I should have known better: the tubular was probably as old as the bike — three decades or more — and the rear blew out on a test ride the day before. I rode along a bit further. With a weak knee, out of shape legs and lardo at the aid stations, it’s not like I was gunning for a PR. Then an Italian guy pulled over, took a spare tubular off his back and got me back on the road to Gaiole. It was used, the valve was stuck open and we didn’t have any glue, but as long as I didn’t corner fast I’d make it out of L’Eroica in one piece.

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Yes, the Italians are good people, I thought, and wrapped the shredded tired over my shoulders like a backpack and figure eight across my back, as appeared to be the custom, not wanting to soil the bucolic Tuscan countryside. The scenery is just one of the things that’s made L’Eroica one of the greatest organized rides in the world since Giancarlo Brocci founded it 30 years ago to help preserve the strada bianche, or white sand and gravel roads of Tuscany. There’s the quintessential town of Gaiole in Chianti with cobblestone streets; the pre-race markets with leather helmets, ancient components and porchetta; the mechanic who is also the post-race DJ; the requirement that all bikes must be steel, and built before 1987; the men and women in period garb; riding with this guy; stopping to eat grapes from the vine; aid stations with olive oil-soaked bread, Chianti and lardo. And not a single bit of it artificial or unnatural — there’s too much cycling history here. It’s too deep in the countryside.

Featured font: Velo Serif from foundry, House Industries. Learn More

Featuring Velo Serif from foundry, House Industries. Learn More

Our ride slowed considerably after the flat, but not (entirely) from the mushy handling. It was rather from the cream-filled doughnut we ate just after the lardo and the brief stop to hand out leftover capicola to other riders. Sure, there’s a place at L’Eroica for Ironman types: a 209-km ride with 12,000 feet of elevation change, which, on old bikes and gravelly roads, is a 15-hour day. We took a much shorter route, though, as we had to rest up for the long dinner ahead of us.

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