Plovdiv has been lived in for something like eight thousand years, and it is one of the oldest continuously inhabited cities in Europe. It grew on a cluster of rocky hills rising out of the Thracian plain beside the Maritsa river, and each age has left its layer. Philip II of Macedon took the Thracian town and gave it his name, Philippopolis; the Romans made it a major city; the Ottomans called it Filibe; and the merchants of the National Revival filled the old town on the hills with colourful houses with jutting upper storeys. Walking through it is like flipping through a stack of history books.
The Roman remains are the stars. The theatre, found by chance in the 1970s after a landslide, sits on the slope of the old town with views across the city and is still used for concerts and opera in summer. Part of the Roman stadium lies under the main pedestrian street, where you can look down at its curved seating from the pavement. Above, in the old town, the Revival houses, several of them museums, line the cobbled lanes, and nearby the Kapana district, once the craftsmen's quarter, is full of bars, cafes and street art. The city was a European Capital of Culture in 2019, and it has a lively, youthful feel.
Plovdiv is a big city, and riding in it means dense traffic and drivers who treat lanes as suggestions. The city itself is not a riding destination, but it is a superb base for the mountains to the south. The road toward Asenovgrad leads into the Rhodopes, with the Asenova fortress perched above the gorge and the Bachkovo monastery, one of the most important in Bulgaria, a few kilometres further. Beyond, the road climbs through the narrow Chepelare valley, a wonderful ride with bends and rock walls, toward Pamporovo and Smolyan. To the north, the Rose Valley and the Balkan range are within easy reach.
Plovdiv has every service you could want: fuel, motorcycle shops, hotels and restaurants of all kinds. Park outside the old town and walk in, as the cobbles of the hills are steep, rough and slippery, and much of the centre is pedestrianised. Summers are very hot, often above thirty-five degrees, so plan sightseeing for the morning and evening. The terraces of Kapana come alive after dark.