The mass ride - a spin-off from an annual autumn event in the nearby Chianti wine country - is the latest in a series that celebrates professional cycling's noble values of team work and self-sacrifice.
It also seeks to promote the preservation of the "strade bianche" (white roads), the gravel paths that are as much a part of the region's famous landscape as olive groves and cypress trees.
Participants had the option of various circuits, ranging from 46 kilometres (28 miles) to 171 km (106 miles), through the bucolic countryside around Montalcino, much of it covered in vines that produce the grapes for one of Italy's most revered wines, Brunello di Montalcino.
The town's mayor, Silvio Franceschelli, said the "Eroica", whose model has been exported around the world, was a fine example of the gastronomy-based, environmentally-friendly tourism that regions like Tuscany are seeking to develop.
Photo: Alberto Pizzoli/AFP
"It is the perfect marriage between the things we do very well and the relaxed way of getting around that we want our visitors to enjoy," Franceschelli said.
Organisers say the Eroica, founded in 1997, is about celebrating the golden age of pro cycling in the 1960s and 1970s and especially the unsung heroes of that era, the "domestiques", the team riders whose efforts were so important to delivering victories for the big names but never got a fraction of the glory.
The Eroica, they say, is "a ride not a race" and the message they are trying to pass on to a new generation is: "There was once a man who won because he knew how to lose."
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