You won’t find Plovdiv, the second largest city in Bulgaria, on most people’s radar — but it should be. Why? It’s the oldest continuously inhabited city in Europe. Since Neolithic peoples first settled here in the 6th millennium B.C., it’s been home to everyone from the Thracians to the Romans to the Ottomans. Not every civilization left a visible mark, but there’s more than enough here to please the ardent history lover.

This post will guide you in seeing Plovdiv through time in a single day. You’ll find the city’s historical buildings and archaeological sites scattered across its three hills and many neighborhoods, so your walking route won’t necessarily follow any chronological order. Keep your eyes out for sites wherever you go.

The Roman Era (72 BC – late 300s AD)

It’s easy to step back into the glory days of Rome in Plovdiv — ancient ruins stretch all over the city.

Start at the Ancient Theatre of Philippopolis, which was constructed by the Romans late in the first century AD. (An important side note: in 342 BC, Philip II of Macedon — the father of Alexander the Great — conquered Plovdiv and named it after himself, so it was called Philippopolis throughout the Roman Era). Built to seat around 7,000 spectators, this theater was likely used for gladiatorial fights and other events. Over time, locals built over and then forgot the theater — until a landslide in the 1970s brought its remains to light. Today, the expertly excavated theater once again hosts performances (though thankfully, no lion fights).

You can see plenty of other Roman ruins as you walk through the town. Two of the most important are the Odeon of Philippopolis (the city council’s meeting place) …

… and the Ancient Stadium (a 2nd century AD construction that now runs a full 240 meters beneath a pedestrian street).

What happened to the Romans in Plovdiv? As the Western Roman Empire began to decline, the city faced invasions from various groups, including the Huns, Slavs, and Bulgarians (even Attila the Hun got in on the action, badly damaging the Philippopolis theater in the 5th century). Plovdiv — often still known as Philippopolis — bounced among Bulgarian, Latin, and Byzantine control in a dizzying sequence of wars and occupations. You can still see evidence of at least one of these invading empires today.

The Byzantine Era (intermittent throughout the 600s–1300s, with control constantly being lost and regained)

The Byzantines didn’t have an easy time holding onto Plovdiv, but they did leave their mark. If you need a refresher, the Byzantines essentially constituted a continuation of the Roman Empire in the east. But while the Byzantines preserved many Roman laws and traditions, they were based in Constantinople and were deeply Christian from the moment their empire began.

That commitment to the Christian faith means that one of the best places to see their influence is at the Bishop’s Basilica of Philippopolis, also known as the Great Basilica. The mosaics here offer glory to God through both Christian symbolism and an unusual abundance of birds.

Truth be told, no one knows exactly why the floor of the basilica is covered with more than seventy different bird species, but the layout is remarkable — and I would argue that the basilica is one of the highlights of a Plovdiv visit today. I was so impressed that I wrote an entire post about it.

The Ottoman Era, 1371-1885

The Ottomans came in and settled down — they were around for a long time. They changed the city’s name to Filibe, established the area as a major trading hub, and built mosques and baths throughout the town (those are the Chifte Baths above; built in the 16th century, they’ve since been converted into a contemporary art museum).

It’s impossible to miss the Ottoman impact on Plovdiv, because minarets rise high in the skyline.

Dzhumaya Mosque, also known as the Friday Mosque, sits smack at the city center. The current building, topped with nine lead domes, dates to the 15th century.

It’s well worth covering your shoulders and stepping inside to see the wall paintings, which were added in the late 1700s and early 1800s.

Bulgarian National Revival (late 1700s-1800s)

Plovdiv became a major economic center under the Ottomans, some say second only to Constantinople. While the Bulgarian lands were by no means rich, merchants were able to consolidate wealth in Plovdiv — and with great riches often come great houses.

At the same time, ethnic Bulgarians in Plovdiv were beginning to chafe against Ottoman rule. In response, they began expressing their identity by building their homes in a nationalistic architectural style known as Bulgarian National Revival — think overhanging floors, dark wooden timbers, white outlines, and lots of eye-catching paint.

Why the unusual overhang? It was a clever way to maximize space on narrow streets, protect pedestrians from the weather, and get more upper-floor living space while being taxed only on the ground floor area below.

The best place to see these buildings is in what’s now called Old Town. A good number of them have been turned into museums — including the pinkish-red Klianti House, with its fantastic carved wooden ceilings, and the yellow Pharmacy Museum Hippocrates, where you can still see blue and white bottles on the shelves.

An excellent spot to get a sense of the area’s culture and history is at the Kuyumdzhieva House, a merchant’s residence built in 1847, which now houses Plovdiv’s Ethnographic Museum.

Here, you can peek into period rooms (both modest and wealthy), see examples of traditional crafts, and learn about regional agricultural and manufacturing practices.

Bulgarian National Revival architecture even made it into Old Town churches, such as the beautifully-painted 1832 Church of St. Constantine and Helena. If you’re interested in art history, make sure to take a peek inside — the church is known for its frescoes, which were painted by masters of the Debar School during the Bulgarian National Revival period.

The best place to see history layered on top of itself in Plovdiv is at the Old Town’s Hisar Kapia, or Castle Gate. Here, you’ll find Bulgarian National Revival-era houses built hovering over a medieval gate constructed during the Second Bulgarian Empire. That gate, in turn, was built on top of Roman foundations; the first gate in this spot dates to the second century AD.

Third Bulgarian State (1878-1946)

Bulgaria finally succeeded in throwing off Ottoman rule in the late nineteenth century, at which point Plovdiv became the capital of an autonomous region known as Eastern Rumelia. After a bloodless revolution, Eastern Rumelia and Bulgaria united in 1885, and Plovdiv began to grow as an industrial center.

This growth meant that Bulgaria finally saw real economic development — and with money came national ambition. Plovdiv, the second-largest city in the country, was able to recruit architects to build in all of the trendy styles of the day (think the “neos”: Neo-Baroque, Neo-Rococo, Neo-Renaissance, and Neoclassicism). The current Plovdiv Town Hall (above), built in 1912, was influenced by the Italian Renaissance — all columns and arches with a dome on top. You can see other good examples of these architectural shifts as you look down the city’s main pedestrian street: check out the Neoclassical symmetry of the yellow 1910 Molle Hotel, and the clean Art Deco lines and celestial sculpture of the grey-blue 1923 Atlas House just beyond. The city was changing shape.

The Communist Era (1944-1986)

Everything changed after World War II. When the Soviets moved into the Balkans in 1944, they immediately seized Bulgaria and incorporated it into a resistance movement known as the Fatherland Front. In 1946, the Fatherland Front established the People’s Republic of Bulgaria, and it became one of the most loyal satellite states of the Soviet Union for the next forty years.

The Communist regime altered nearly every aspect of life in Plovdiv, from industry and agriculture to personal freedoms and artistic expression. One look out over the city, and you can see the marks this era left on its facade: anything grey, blocky, and featureless was probably built during the Communist era.

I’ll admit that it’s not my favorite architectural period, but the Communist era is an important part of Plovdiv’s history — and it’s controversial, since many people would like to see the grey monuments of that time torn down). Should you want to see examples of Communist-era building up close, you can visit the National Library “Ivan Vazov”, the Alyosha Monument, the Headquarters of the Communist Party, or the Grand Hotel Plovdiv (this is a mural from the lobby).

Modern Times: The Kapana Creative District

Bulgaria has come a long way since casting off the communist yoke. To see how Plovdiv has changed, it’s worth ending your day in the Kapana District. Kapana literally means “The Trap,” so named for the warren of streets that once housed Plovdiv’s craftspeople. Kapana is a perfect representation of what Plovdiv has become over the course of the past few decades: creative, fun, and lively. In 2019, the EU named Plovdiv named Capital of Culture, and it’s easy to see why as you wend your way through the Kapana’s many shops, restaurants, and small galleries.

I loved Plovdiv — I wish I’d given the city two or three days instead of just one, and I hope you enjoy it as much as I did.

Need help finding these spots as you walk through Plovdiv’s history? Here’s a custom map to guide you along your way.

Further Reading: After Your One Day in Plovdiv

• If you’re planning to spend time in Sofia, Bulgaria’s capital, check out my one-day itinerary here.
• Want to explore the nearby Bulgarian countryside? Take a look at my post on the wonders of the Rhodope Mountains.