Plovdiv is one of the oldest continuously lived-in cities in Europe, and it wears its age with a kind of cheerful disorder. People have lived on these rocky hills beside the Maritsa River for some eight thousand years, and the Romans, who called the city Philippopolis, left a theatre that is still used for concerts, carved into the hillside and facing out across the rooftops. The name comes from Philip II of Macedon, who took the town in the fourth century BC. With about three hundred thousand people, it is Bulgaria's second city, and it has every kind of shop and fuel station you might need.
The old town sits on three of the city's famous hills, with cobbled lanes, painted wooden houses from the Bulgarian National Revival and a huge variety of galleries and cafés. Below it, the Kapana district, a tangle of narrow streets, is the place to find coffee, craft beer and small restaurants, and it was a big part of the city's year as European Capital of Culture in 2019. Bulgarian food here is very good: shopska salad, grilled meats, cold yoghurt soup and rakia, a fruit brandy that arrives at the table whether you ask for it or not.
For the ride, Plovdiv is the flatland start before the mountains. The Thracian plain is warm, fertile and flat, with fruit orchards and roses, and the Rhodope range rises as a blue wall to the south. You head toward Asenovgrad, past the ruined fortress of Asen and the Bachkovo Monastery, founded in the eleventh century and one of the great Orthodox sites of the country. From there the road tightens into the Rhodope gorges, with rock walls, pine forest and the first of the hairpins.
Traffic in Plovdiv is chaotic in the way of southern European cities, with impatient drivers and tram-like confidence, so give yourself room. Fuel is cheaper than in western Europe and widely available, and you should top up before you climb, since the mountain villages are small. Summer is hot, up in the thirties Celsius, so a morning start is wise; spring and autumn are gentler, and the plain is lovely when the roses bloom in late May and June.