One of the largest Roman structures on the Balkan peninsula, the ancient Stadium of Trimontium is mostly buried beneath the city, except for its Northern part, which is uncovered and open to visitors. Next to the excavated section, there is a miniature model of the stadium as it stood when it was built at the beginning of the 2nd century AD, during the reign of Emperor Hadrian. With a length of 240 m and a width of 50 m, it could seat up to 30,000 spectators. Some seats are engraved with names in Greek, proving there were seats specifically designated for people of high status. Games similar to the Pythian Games in Greece were held here, organized by the General Assembly of the province of Thrace.

This unique architectural museum contains buildings in the style of the Bulgarian Revival Period, ancient Roman and Thracian ruins, various monuments and landmarks, all coming together to perfectly illustrate the complicated history that has shaped this city into the Plovdiv of today.

The crown jewel of this city is the Roman Theatre, also known as the Ancient Theatre of Philippopol – one of the best preserved in the world. Nestled in the saddle between two of the three hills upon which the Old Town is built – Dzhambaz Tepe and Taksim Tepe – it overlooks the southern side of the city. It was constructed in the 1st century AD and used for theatre performances, gladiator games and hunting spectacles. Inscriptions mark the seats reserved for notable member of Roman society, as was customary in the region at the time. The inscriptions imply that the theatre was also used as the seat of the Thracian Provincial Assembly. It can hold between 5000 and 7000 spectators and is still in use today as a stage for opera, music concerts, and other cultural events, the most famous of which is the “Opera Open” summer festival.

The original church was built in the year 337 on the site of an older, pagan temple. Named after the Roman emperor Constantine the Great and his mother Helena, it has been destroyed and rebuilt several times over the course of its history. It contains icons by the famous Bulgarian painter and iconographer Zahari Zograf. The church as it stands today was constructed in 1832, making even its current iteration the oldest church in Plovdiv.

This medieval gate, built in the 11th century AD, stands on the foundations of an even older, Roman-period gate, and was once the Eastern entrance to the acropolis of ancient Plovdiv. Today the gate is framed by Revival Period houses built into the walls of the former fortress.

On the western side of Hisar Kapia is the Plovdiv Regional Ethnographic Museum. Housing a collection of 40 000 cultural artifacts, including furniture, musical instruments, clothing, pottery, tools and household objects, it offers a unique look into the lifestyle of the people who inhabited this region in the past. The museum itself is an intricately decorated Bulgarian Revival Period house heavily featuring Baroque elements.

The Old Town of Plovdiv stands atop three syenite hills, and the northernmost one is known as Nebet Tepe. Here is where Plovdiv's oldest iteration once stood - a settlement that was founded all the way back in the Copper Age and eventually grew into the ancient Thracian city of Eumolpia. The ruins of its fortress still stand over the rest of the city and are accessible to visitors. The hill also offers a gorgeous panoramic view of the eastern, northern and western sides of Plovdiv.

Balabanov House is a stunning example of Bulgarian Revival Period architecture, known for its impressive architecture, furniture, wall paintings, intricate woodcarvings on the ceilings – a unique design in each room – and artworks. The ground floor acts as an art gallery displaying a permanent exhibition of modern Bulgarian art. The second floor is lavishly furnished with late Baroque furniture.

Built in 1835-1840, and originally owned by the merchant Stepan Hindliyan, this historic house-museum is a stunning example of Symmetrical Plovidv Architecture. With its Neo-Baroque design, intricate ceilings and the detailed landscapes handpainted on its walls, the Hindliyan house is the most richly ornamented of all preserved houses in the Old Town. The niches on the interior walls are decorated with wall murals depicting scenery from Stockholm, Lisbon, Saint Petersburg, Athens, Istanbul, Venice, most likely reproduced from postcards and engravings the owner of the house brought back from his travels. The large living room has a fountain through which rose water circulated and filled the room with its fragrance. Inside is the only preserved fully functional bathroom with running cold and hot water. Stepan Hindliyan and his family lived inside this house up until 1915, when the Turkish persecution of Armenians began. The merchant left his home to Armenian refugees in search of shelter. 23 Armenian families lived in this house up until 1974, after which they were rehoused and the building was declared a cultural landmark.

Kapana, also known as the Trap, is the art district of Plovdiv. It first emerged as a center for craftsmen in the 15th century and has since grown into a hub for artists of all kinds. It is made up of a labyrinth of intertwining cobblestoned streets lined with workshops, modern art stores, stylish little cafes and restaurants, and even the facades of the buildings are works of art in their own right, colorfully painted by talented street artists and further enhanced with constantly changing pieces of modern art scattered around every corner.