October’s L’Eroica permits only bikes and gear from 1987 or prior (or replicas). Held in the province of Siena, the event has been dubbed “one of the best bike rides in the world” by Cycling Weekly, and it’s not hard to see why. What can be more picturesque after all than Tuscany in autumn? Red terracotta roofs, silvery cypresses, and the famed chalk-white roads, or strade bianche…

There is something timeless about riding these pale strade on vintage two-wheelers, minus all the modern bells and whistles. A L’Eroica bike must be steel-framed with downtube shifters, have 32-spoke wheels, and pedals with toe clips (sorry—clip-in pedals are strictly proibito). 

If you show up sporting modern digs, you’ll be politely encouraged to visit the stalls offering more authentic cycling clothing (for a price, of course). The event offers a range of routes, from 46 to 209 km. As a final nod to history, all routes begin and end in the idyllic town of Giaole, home of the inventor of the legendary recipe for Chianti wine.