5 Days in Plovdiv

In the middle of Dzhumaya Square, steps lead down below the street to the curved end of the Roman Stadium, built in the 2nd century under Hadrian. It was about 240 m long and seated some 30,000 people for athletic games, not gladiators. The rest of it still lies under the main street and the buildings on either side. A short 3D film in the small hall next to it brings it back to life, and a combined ticket adds the stadium's eastern sector, preserved inside a building at Knyaz Alexander I 11.

Above it stands the Dzhumaya Mosque, the symbol of Ottoman Filibe. The first mosque here went up soon after the Ottomans took the city in the 1360s; the building you see, with nine domes and a striped brick minaret, is from the 15th century. You can go in outside prayer times. Next door, a café serves Turkish coffee and lokum.

Walk south along Knyaz Alexander I, the long pedestrian street the locals call Glavnata, the Main. It's lined with 19th- and early 20th-century buildings, cafés and shops, and it's where Plovdiv strolls in the evenings. Halfway down, look for the bronze statue of Milyo, a local eccentric of the 1970s who loved to listen in on conversations.

At the southern end, by the Central Post Office, lie the remains of the Roman Forum, the main square of Philippopolis, and next to it the Odeon, a small theater of about 350 seats that was the city council hall.

After lunch, walk to the Bishop's Basilica of Philippopolis, the largest early Christian church in Bulgaria, from the 4th to 6th centuries. Its floors, about 2,000 square meters of mosaics on two levels, were uncovered in excavations and opened to the public in 2021 under a modern protective building. The birds stand out: peacocks, ducks, pheasants and dozens of other species, the symbols of paradise, laid out in bright stone.

Next door stands St. Ludwig, the largest Catholic cathedral in Bulgaria. A separate combined ticket adds the Small Basilica, a few minutes east, and the Irene building with its house mosaics in the underpass on Tsar Boris III Boulevard.

The Ancient Theater of Philippopolis, built under the emperor Domitian at the end of the 1st century, sits on the slope between two of the city's hills, Dzhambaz and Taksim Tepe, seats several thousand people, with a view over the modern city and the Rhodopes beyond. It lay buried for centuries until a landslide uncovered part of it, and it was excavated between 1968 and 1979. Its marble seats and the stage building have been restored, and it's in use again: in summer, the Opera Open festival stages opera and concerts here.

Come in the late afternoon, before it closes at 6pm (5:30pm in winter). It's a theater, not an amphitheater, whatever the souvenir shops say.

Kapana is a tangle of narrow streets north of Dzhumaya Square. The name means the Trap, and locals joke it's because you get lost, but it really comes from the Turkish kapan, a covered market and public weighing place: two of them stood here in the 15th century, and by 1652 the quarter had 880 shops. The streets still carry the names of the crafts: Zhelezarska (ironmongers), Kozhuharska (furriers), Abadzhiyska (cloth makers) and Zlatarska (goldsmiths). It burned in 1906, was almost demolished for a shopping center in the 1970s, and for the European Capital of Culture year in 2019 it was turned into Plovdiv's creative quarter, full of galleries, street art, small bars and restaurants.

Pavaj, on Zlatarska street, is a locals' favorite for modern Bulgarian food. Start with a shopska salad and, if it's warm, a bowl of tarator, then try a kavarma in its clay pot. Afterwards, Cat & Mouse, open since 2015, has more than a hundred beers.

Enter the Old Town through Hisar Kapiya, one of the three gates of the acropolis, rebuilt in the 11th century on Roman foundations, with houses built right up against it. A few steps on is the Church of Sts. Constantine and Helena, the oldest church site in the city, where Christians are said to have worshipped since the 4th century. The present building dates from 1832, and its icons include works by Zahari Zograf, the great painter of the Bulgarian Revival.

In the 19th century, Plovdiv's merchants grew rich on trade between Europe and the Ottoman Empire, and they built themselves houses that showed it: colorful facades, upper floors jutting out over the street, painted ceilings and Viennese furniture inside. Several are open as museums. Hindliyan House, built in 1834-35 for an Armenian merchant, has painted walls and its own marble bath. Balabanov House next to it hosts concerts and exhibitions, though it's a reconstruction from 1976-79. Nedkovich House shows a wealthy family's rooms in Viennese style.

Then wander. Klianti House, one of the oldest, is open every day; Chomakov House shows the work of Zlatyu Boyadzhiev, the great Plovdiv painter of the 20th century; there's a small pharmacy museum on Saborna street, and the church of St. Marina has a carved wooden bell tower.

Have a long lunch in one of the restaurants with gardens in the Old Town, such as Philippopolis on Saborna street, with views over the city; ask for whatever is local that day. Try sarmi, vine leaves stuffed with meat and rice, and finish with kiselo mlyako, the famous Bulgarian yogurt, with honey and walnuts.

After lunch, by Hisar Kapiya, visit the most photographed house in Plovdiv, the Kuyumdzhiev House, built in 1847 for a rich merchant: a symmetrical facade painted blue and covered in garlands, with a curving baroque gable. Inside is the Regional Ethnographic Museum, with costumes, jewelry, crafts and musical instruments from Thrace and the Rhodopes, and rooms furnished as a merchant family lived. Sit in the garden afterwards.

At the northern edge of the Old Town is Nebet Tepe, the hill where Plovdiv began. People lived here from the 5th millennium BC, and the Thracians, Romans and Byzantines all fortified it; you can still see walls, a gate and a postern passage that is thought to have led down to the river. From the top you look over the Maritsa and the whole city, with the Rhodopes on the horizon, and at sunset the young of Plovdiv gather up here.

Above the gorge of the Asenitsa river, a medieval fortress stands on a rock with sheer drops on three sides. It's named after Tsar Ivan Asen II, who rebuilt it in the 13th century, and what's left is mostly walls and one beautiful survivor: the Church of the Holy Mother of God of Petrich, with a tall tower and frescoes from the 14th century inside. The view runs down the gorge and out over the Thracian plain.

Bachkovo was founded in 1083 by two Georgian brothers in the service of Byzantium, Gregory and Abasius Pakourianos, and it's the second-largest monastery in Bulgaria after Rila. Around its cobbled courtyard stand churches covered in frescoes, and in the main church an icon of the Virgin, believed to work miracles, draws pilgrims from all over the country.

Dress modestly. The founder required his monks to know Georgian, and the monastery kept its Georgian character for centuries. Pay a little extra for the old refectory, whose walls are covered in 17th-century frescoes, including a Tree of Jesse and philosophers of antiquity. A short walk away, the ossuary has frescoes from the 11th-12th centuries, older than anything in the monastery itself. Outside the gate, stalls sell honey, herbs and homemade jam.

The restaurants by the river below the monastery serve fresh trout from the Rhodope streams and kebapche, cumin-spiced grilled minced meat, with fries and white cheese. On the way back, look for stands selling kozunak and pastries.

Asenovgrad is the home of Mavrud, Bulgaria's own dark red grape, which makes a heavy, spicy wine. The legend says Khan Krum had the vineyards destroyed, until a young man named Mavrud killed a lion, and his mother revealed she had secretly kept a vine and made wine from it; Krum was so impressed that he had the vineyards replanted. Stop at one of the wineries around Asenovgrad for a tasting (the tourist office's wine route map lists them), and book ahead. If you're driving, let a passenger taste.

Back in Plovdiv, spend the evening in one of the taverns of the Old Town, quieter than Kapana and lit up along the cobbled lanes. Try a glass of rakia or a mastika, the anise spirit, with a plate of white cheese and lyutenitsa.

High in the forest, a river has carved two enormous arches through the marble rock, the Chudnite mostove, or Wonderful Bridges. The larger is about 45 m high and 96 m long, and you can walk both over and under it. Outside summer weekends it's almost empty. Paths lead down into the gorge and up onto the arches.

The Rhodopes have their own cuisine, simpler and heartier than the plains. Look for patatnik, kachamak and local mountain trout. Wash it down with ayran, the salty yogurt drink.

Shiroka Laka is a village of white stone houses with dark wooden upper floors, stone bridges over the stream and slate roofs, a protected architectural reserve of the Rhodopes. It's home to a national school of folk music, and Rhodope singing, slow, ornamented and accompanied by the deep sound of the kaba gaida bagpipe, is the sound of these mountains. Look in at the Church of the Holy Mother of God, from 1834, which legend says was built in 38 days. On the first Sunday of March the village holds a kukeri festival, with dancers in huge masks of fur and bells chasing away winter.

Drive back to Plovdiv for a late dinner in Kapana: grilled meat, a salad and a glass of local red. Kapana is at its liveliest at the end of the week.

On Saedinenie (Unification) Square, the Regional Archaeological Museum covers Plovdiv's long history, from Neolithic figurines to Thracian silver, Roman statues and medieval ceramics. Its best-known treasure is the Panagyurishte hoard, nine Thracian vessels of 23-carat gold weighing over 6 kg, found in 1949; it belongs to this museum, but the original is kept in the National History Museum in Sofia, so here you see a replica. The Roman finds from Philippopolis itself are the real highlight.

Five minutes north is the Imaret Mosque of 1444-45, with a minaret of zigzag brickwork and the tomb of its founder, Shahabeddin Pasha.

After the Russo-Turkish War, the Congress of Berlin in 1878 split the new Bulgaria into three, and Plovdiv became the capital of Eastern Rumelia, an autonomous Ottoman province. On 6 September 1885, rebels in Plovdiv overthrew the governor and declared union with the Principality of Bulgaria, a bold move that led to war with Serbia, which Bulgaria won. The monument on the square marks the event, and 6 September is still the Day of Plovdiv. The Regional History Museum nearby tells the story.

After lunch, climb Sahat Tepe, the Clock Hill, above the Main Street. On its top stands the clock tower, a stone tower from 1809-12 on a site with a clock since around 1600, one of the oldest in the Balkans; it has no dial and still strikes the hours. The hill is green and quiet, with paths through the trees and views over the rooftops to the Old Town opposite.

West of the center rises Bunardzhik, the Hill of the Liberators, topped by Alyosha, an 11 m statue of a Soviet soldier put up in 1957. The Red Army entered Plovdiv in September 1944 without a fight, so it marks no battle, and after 1989 there were several attempts to remove it. Each time, protests kept it in place, and it has become part of the skyline. Walk up for the widest view of the hills, including Mladezhki Halm, the biggest, where locals go for long walks; there are six now: the seventh, Markovo Tepe, was quarried away in the 20th century to pave the city's streets.

At the southern end of the Main Street is Tsar Simeon Garden, the city's historic central park, laid out in 1892 by the Swiss gardener Lucien Chevalas. On Saturday evenings at 8:30pm, in season, the Singing Fountains on its lake put on a show of water, light and music.

Then walk back up the Main Street for a farewell dinner in Kapana or the Old Town: a shopska, a kavarma, a bottle of Mavrud or Rubin and banitsa or baklava to finish. Nazdrave. Plovdiv was also the birthplace of Kamenitza, founded here around 1881 by two Swiss engineers; most of it is now brewed in Haskovo, but a small brewery still works on the original site.