A Place to Add to Your Bucket List – Discover Plovdiv, Bulgaria

Discover the cobblestone streets, colorful Bulgarian Revival architecture, and ancient Roman ruins of Old Plovdiv — one of Europe’s oldest continuously inhabited cities. A bucket-list destination for history and culture lovers, Plovdiv blends centuries of heritage with modern flair. Photo: R Cowden

Step Back in Time: Exploring the Charm of Old Plovdiv, Bulgaria

If you’re looking to add a fascinating and off-the-beaten-path destination to your bucket list, let me introduce you to Plovdiv, Bulgaria—one of the oldest continuously inhabited cities in the world. With over 6,000 years of history, Plovdiv offers a remarkable blend of ancient ruins, vibrant art, and lively culture—all set against a backdrop of cobbled streets and charming hills.

I visited last summer after a Danube River Cruise, and immediately wished I had at least another full day.  Plovdiv, and Bulgaria in general, turned into a highlight of my recent travels!

Read on for more and schedule a call at the link to start planning, wherever you have in mind to discover in 2025 or 2026!

A charming pedestrian zone with stunning architecture and vibrant cafe culture, even a rainy morning can't dim the beauty of this hidden gem. Photo: R Cowden

Why Plovdiv Belongs on Your Travel Bucket List

A Crossroads of Civilizations

Plovdiv's history stretches back to the 6th millennium BCE, which ranks it, by far, as the oldest city in Europe.  

It rose to prominence as the ancient Greek city of Philippopolis in the 4th century BCE when it was conquered by Philip II of Macedon (father of Alexander the Great). Under Greek rule, it became an important cultural and trade center, and you can still see traces of this legacy in its ancient walls and artifacts.

Learn how to read wall, 2,500 years in the making! The bottom stones are Greek from Philip of Macedon's time and the founding of Philipopolis; anywhere in the former Roman world that you see thin flat bricks, which you can see on the second layer from the bottom, are Roman; the large blocks are from the Eastern Roman Empire (Byzantine); next are the Ottoman stones; finally Republican Bulgarian. Photo: R Cowden.

Plovdiv's 2nd Century Roman Amphitheater, beautifully preserved, stands ready for modern summer concerts amid historic architecture and scenic views.

Roman Influence

After the Romans took control in the 1st century AD, Plovdiv flourished as a major city of the Roman Empire. The remarkably preserved Roman Amphitheater—carved into a hillside and still hosting concerts today—is one of the best-preserved in the world. The remains of the Roman Stadium and sections of the city’s aqueducts give you a window into life during Roman times.

Historic Ottoman architecture in Plovdiv featuring characteristic tile roofs and artful overhanging extensions that cleverly expanded living space while avoiding land taxes. Photo: R Cowden

Ottoman and Bulgarian Heritage

In 1364, Plovdiv became part of the Ottoman Empire.  Over the course of 5 centuries, the city was adorned with beautiful mosques, baths and iconic residential architecture. 

Bulgaria was “liberated” in the 19th century by the Russians who were attempting to reach Istanbul.  Plovdiv became a center of Bulgarian revival, and the beautifully preserved 19th-century houses in the Old Town reflect this artistic and architectural renaissance.

Today, the city is also a university town, giving an energetic vibe one expects in similar towns.

Old Town Charm

Plovdiv’s Old Town is a maze of beautifully preserved 19th-century houses, now home to galleries and museums. The city’s architectural mix of Greek, Roman, Ottoman, and Bulgarian styles creates a unique sense of place. The colorful, wood-framed houses with overhanging balconies are some of the finest examples of Bulgarian National Revival architecture.

Images: a scenic evening stroll through the historic district of Plovdiv, Bulgaria. Photos: R CowdenR Cowden

Charming early 20th-century architecture lines the vibrant, cobblestone streets, where string lights illuminate cafes and boutiques in a picturesque setting. Photos: R Cowden

Creative Vibe in the Kapana District

Kapana (“The Trap”) is Plovdiv’s arts and culture hub—but it wasn’t always this vibrant. Once a neglected part of the city, Kapana has undergone a remarkable urban renewal, transforming into a lively pedestrian-friendly neighborhood filled with cafés, artisan shops, and street art.

Once the city's bazaar, it burned to the ground in the early 20th century and was rebuilt in the era following independence, giving it a very different style of National Revival building.  But it fell into disrepair and abandonment in the communist era.

The area’s revitalization began with Plovdiv’s successful bid to become the 2019 European Capital of Culture, which spurred investment and creative energy. Today, Kapana’s colorful streets are a symbol of Plovdiv’s modern artistic spirit. You’ll find locally roasted coffee, handmade crafts, local boutiques, live music, all set within a charming, historic backdrop. Its success as a model of urban renewal has made it a destination in its own right.

Photos: European Capital of Culture marker and the bohemian vibe of Kapana.  Photos: R Cowden

The Roman Hippodrome in Plovdiv, creatively integrated beneath the bustling pedestrian street, showcases the city's innovative effort to blend ancient history with modern urban life. Photo: R Cowden

Must-Do’s in Plovdiv

✅ Explore the Roman Amphitheater – Built in the 2nd century AD, this hillside amphitheater is still used for concerts and events, offering breathtaking views over the valley.

✅ Visit the Roman Stadium and Hippodrome – A major archaeological project is underway to open more of the ancient Roman Hippodrome to public viewing. For now, you can see the rounded end of the stadium beneath the glass floor of a local bar—a fascinating way to sip a drink while overlooking ancient history.

✅ Discover the Most Unusual H&M You'll Ever Visit – Plovdiv’s H&M is built over the Roman Stadium, with sections of the ancient structure visible beneath glass panels on the shop floor—a mix of modern retail and ancient history. Photos below.

✅ Admire and Explore the Residential Architecture – Many of the homes in the old town are museums and open for a visit.  The Ethnographic Museum being one, but several others are also open and house specialty museums, they are also art museums in their own right due to their intricate details.

✅ Ethnographic Museum – Housed in a stunning 19th-century mansion, referred to as the “House of 100 Windows” (another way of flaunting your wealth as there was a tax on windows) this museum showcases Bulgarian folk costumes, crafts, and domestic artifacts.  Of particular interest are the felt and other handicrafts of Bulgaria. The beautifully preserved Ottoman-era courtyard and gardens are a wonderful retreat.

Above: The 2nd-century Roman Hippodrome is illuminated at night, with a former Ottoman mosque elegantly situated above, showcasing layers of history. Below: he city has worked to open the structure creatively such as the two bottom left photos, INSIDE the H&M. R Cowden

Photo Above: the garden lined entry to the Ethnographic Museum of Plovdiv; Photos Below: the ornate interior of the mansion with stunning decor plus beautiful Bulgarian crafts.

Temple of the Archangel in Plovdiv, showcasing its elegant architecture and intricate iconography under a clear blue sky. Photo: R Cowden

Plovdiv, and Bulgaria overall, were a spectacular surprise. Reasonable costs and fewer crowds made it an instantly loveable destination.  In a country where I found myself wishing I had more time, I almost instantly wished I had a second night in Plovdiv! 

Let’s craft a journey tailored just for you to find your own unexpected favorite, wherever you have in mind. 

Schedule a conversation at the following link to get started on your next adventure.

https://calendly.com/avidnomadtravel/initial-travel-planning-consultation