Plovdiv, Bulgaria is counted among the oldest cities in the world. Dating back as many as 8,000 years—or just a mere 6,000 years, depending on which expert you ask—its ancient evidence ranges from Neolithic settlements to medieval fortresses. Geographically, the city is planted along the Maritsa River on the main road from Western Europe to Istanbul, an advantageous position between the two continents that enticed many a warlord. Changing hands in antiquity from the Thracians to Alexander the Great’s father Philip II of Macedon, Plovdiv has been occupied by Persians, Turks, Greeks, Romans, and Armenians, among others over the ages.

The millennia of influences have led to the evolution of a place that in many ways mirrors Europe’s most historic cities with its cosmopolitan atmosphere, bohemian character, and intriguing roots. It’s a splendid and fascinating history reflected through the ruins of the Thracian settlement of Eumolpias, the second-century Roman stadium that once hosted gladiator matches, the restored amphitheatre that serves as a performance venue still today, and a diverse collection of places of worship, from Ottoman Mosques to Armenian churches to Gothic and Baroque Christian cathedrals.

Plovdiv is situated across seven separate hills, similar to its fellow ancient city of Rome. Plovdiv’s Old Town encompasses three of these hills and has been restored to reflect its 18th and 19th-century character. The cobblestone avenues are filled with museums and galleries where celebrated artists still live and work. Held annually in September, Plovdiv’s Night of Museums and Galleries plays host to Bulgarian citizens and visitors from across the globe as they mingle in the streets, enjoying free entry into the historic buildings and access to their collections late into the evening.

Modern Plovdiv is a noted hotbed for the arts and was designated one of the 2019 European Capitals of Culture. It’s an incredibly walkable city, with scattered green spaces, fountains, and promenades adding to its charm. The Trakart Museum holds treasures from the Thracian era, as well as part of a Roman villa with well-preserved mosaic floors. Communist-era edifices and abandoned buildings in the Kapana district have been transformed into destinations in their own right, hosting exhibitions and pop-up galleries alongside the vibrant bars and cafes. Ever in competition with Sofia to hold artistic events in its unique confines, the two cities pair nicely on any custom journey to Bulgaria.