• Photo: Kip Malone

    Before carbon frames, wide-range groupos, and specialized nutrition regimens, gritty cyclists pedaled heavy steel steeds down the roads of Tuscany. They wore wool and fueled with bread, prosciutto, and wine, and were celebrated as heroes in a country obsessed with bikes. Today, the spirit of those riders is celebrated with L’Eroica (or The Heroic), a one-day event in October where thousands of people from all over the world sport period kit and pedal vintage bikes (anything produced prior to 1986). The rides, which start in the small town of Gaiole, range from a leisurely 29 miles to an all-day 130-mile sufferfest. All options include plenty of gravel, views of vineyards and ancient castles, and rest stops stocked with the same delicious Italian staples that the old guard relied on.

    Photo: Luciano Berruti’s bicycle carries the #1 rider-number for a good reason: he’s participated since L’Eroica began in 1997. A former racer and avid collector, Luciano runs a bicycle museum, the Museo della Bicicletta, in Cosseria.

  • Photo: Kip Malone

    It’s easy to forget that this photo was taken in 2016.
  • Photo: Kip Malone

    Riders drop out of the forest on Strade Bianche, the famed white gravel roads of Tuscany.
  • Photo: Kip Malone

    Giuseppe Ponzo and his one-candlepower 1920 headlight.
  • Photo: Kip Malone

    Extra tubular tires were part necessity, part fashion accessory.
  • Photo: Kip Malone

    There was also a vintage bike market at the event. It offered a staggering array of bikes, kit, and components, from complete vintage rides to obscure bottom brackets and brake pads.
  • Photo: Kip Malone

    Long before the birth of disc brakes, V-brakes, and cantilever brakes, there were tire brakes. This example on an early 1900s safety bike shows the white mud of the Tuscany roads. Note the wooden rim.
  • Photo: Kip Malone

    Riders make their way through the wet streets of Gaiole to gather for the start of L’Eroica. The town walls reverberated with the sound of old, protesting brake pads.
  • Photo: Kip Malone

    Merino and musette bags cover a sea of cyclists queued up in the center of town, waiting to start their ride. Wool was the jersey material of choice for the vast majority of the 7,000 riders.
  • Photo: Kip Malone

    Tucked in among the cork and steel were a few bits of modern technology.
  • Photo: Kip Malone

    The Tuscan version of a BBQ.
  • Photo: Kip Malone

    A beautiful example of a 1970s Swiss bike from the now-defunct Cilo.
  • Photo: Kip Malone

    The Italians’ love of all things cycling was evident in the many well-preserved bikes at L'Eroica.
  • Photo: Kip Malone

    This wooden-wheeled tandem team was part of a sizeable Japanese group. L’Eroica events are now held in eight countries, including Japan.
  • Photo: Kip Malone

    Historic stage races in Italy often started and ended in the dark, and routes were lit with paraffin candles. Here, candles still burn on the steep climb up to the Castle of Brolio.
  • Photo: Kip Malone

    Jan Culik, 15, from Munich, in front of the 1,000-year-old walls of the Castle of Brolio.
  • Photo: Kip Malone

    Changing a tube in front of a Catholic shrine.
  • Photo: Kip Malone

    Well-staffed rest stops along the route offered up copious amounts of calories from an era before cholesterol screening. There was bread with salami, olive oil, hazelnut spread, and salted whipped lard—all to be washed down with local red wine.
  • Photo: Kip Malone

    Tuscany’s building codes strongly discourage new construction, which means landscapes have been preserved over the past century.
  • Photo: Kip Malone

    Vintage cars and motos like this sidecar Vespa added to the nostalgia out on the roads. This Vespa was there to offer mechanical support to cyclists.
  • Photo: Kip Malone

    This 1960 Moto Guzzi was part showpiece, part support vehicle.
  • Photo: Kip Malone

    An estimated 15,000 people descend on the tiny village of Gaiole for L’Eroica.
  • Photo: Kip Malone

    Italian Nicoca Benciolini enjoys a beer at the finish, 12 hours after the ride started.
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