Ascoli Piceno is made of travertine, and in the right light the whole town looks like it has been carved from cream. The pale stone paves the great Piazza del Popolo and lines the arcades and towers, and the theatre is one of the quiet treats of a place that rarely makes the big lists. It is named after Ventidio Basso, a local boy who rose from humble beginnings to become a general under Mark Antony, defeated the Parthians in the first century BC and, so the story goes, was the first Roman to hold a triumph over them. The people of Ascoli remember it with civic pride.
The theatre itself is a nineteenth-century neoclassical building, handsome and intimate, in the middle of the old town. The town sits where the Tronto river meets a smaller stream, in the Marche region, with the Sibillini mountains to the west and the Monti della Laga to the south, and it feels like a place that has always been slightly out of the way and is quietly content with that. In August the Quintana, a medieval tournament with costumes, drums and competing districts, fills the streets, and it is worth timing a ride for if you like crowds and noise.
For the riding, Ascoli is a very good base. The roads climb west into the Sibillini through the Valle del Castellano and over to Castelluccio, among tight bends, forest and wide upland views, while the valley road towards the Adriatic is fast and easy. Surfaces vary after winter, and sections of road in the mountains have been affected by earthquakes in recent years, so check for closures before committing to a long loop. Summer is hot in the town but delightful in the hills; spring and autumn are best.
Food is part of the point. Olive all'ascolana, large green olives stuffed with meat, breaded and fried, are the local pride and are sold in paper cones, and a small plate of them with a glass of Rosso Piceno is a very good reason to park the bike. Ascoli is a proper city, with several fuel stations around its edges, plenty of cafes in the old centre, and some lovely evening light on the piazza.