8 signature Sofia streets revealing the Bulgarian capital’s charm

“People and streets, a town like any other”, starts a famous Bulgarian popular song from the 1970s. But of course, not quite. Urban spaces define the vibe of a city, and the animated Bulgarian capital Sofia is no exception. In Antiquity reportedly cherished by Roman emperor Constantine as “my Rome”, then described as a “little Vienna” at the turn of the 20th century, and finally hailed as “my little London” by the legendary singer Todor Kolev, modern Sofia is its very own living and breathing Balkan metropolis. Admittedly, its effortless and at times somewhat rough charm has been often misunderstood and neglected – but there is no better way to rediscover it than to get to know its iconic streets!

The foundations of Sofia’s street network date to Ancient Roman times – and the contemporary city centre is still exactly where Roman Serdica used to stand. The city’s urban plan was then shaped by the medieval Bulgarians, before the Ottoman conquest gave Sofia a decidedly oriental character. As it became the capital of an independent Bulgaria in the late 19th century, the sleepy Ottoman provincial town was transformed into a dignified European capital with an Austro-Hungarian twist. Finally, the socialist period brought the world’s “favourite” Soviet-style panel apartment buildings, and the last couple of decades have seen a hit-and-miss influx of modern architecture.

Be it the Bulgarian Broadway, Sofia’s own Little Beirut, the capital’s up and coming arts and crafts district or its aristocratic thoroughfares, kashkaval tourist presents 8 signature Sofia streets revealing the Bulgarian capital’s charm.

1. Little Beirut in the former Jewish district: Tsar Simeon Street

Little Beirut in the former Jewish district: Tsar Simeon Street
Little Beirut in the former Jewish district: Tsar Simeon Street

Stretching for four kilometres through the northern part of the city centre, Tsar Simeon is by some definitions Sofia’s longest street (and not a boulevard, that is). And though for most of its length it’s just a neighbourhood thoroughfare with a notable number of car parts shops, its middle section between the Hristo Botev and Maria Luiza Boulevards is incredibly lively and like no other street in Sofia.

Simeon carries a scent of Middle Eastern spices and moves to the beat of oriental music as it crosses the famous Women’s Market (and no, women aren’t literally sold there). It’s the main street of Sofia’s Little Beirut, an unfavoured but incredibly curious area, a harbour for refugees, Middle Eastern migrants and local Roma. In this part of Simeon, you’ll find dozens of little spice shops, hookah stores, oriental bakeries, halal butchers and especially barbershops, where the old craft of shaving with a straight razor is still masterfully practiced.

This Little Beirut, now populated by many Arabs, was once curiously the Bulgarian capital’s Jewish ghetto. Unlike the rest of Europe, the Bulgarian Jewish community survived World War II, only to move en masse to Israel in the 1940s, leaving this part of the city deserted. Nowadays, the influx of Middle Easterners has breathed new life into the Tsar Simeon area and the beautiful turn-of-the-century townhouses are beginning to regain their grandeur. And fittingly, the synagogue and the mosque are just a block away from Simeon, almost facing each other, with the Market Hall in between.

2. The Bulgarian Broadway: Rakovska Street

The Bulgarian Broadway: Rakovska Street
The Bulgarian Broadway: Rakovska Street

Rakovska, or officially Georgi Rakovski Street, is one of central Sofia’s most prominent and busiest avenues. What sets it apart from other main streets in the Bulgarian capital is its connection to the performing arts and to theatre in particular. The elegant facades on Rakovska and its adjacent streets host literally dozens of theatre venues, including the Ivan Vazov National Theatre, the National Opera and Ballet and the National Academy for Theatre and Film Arts. With this, Rakovska in its part between Slaveykov Square and Dondukov Boulevard has fully deserved its nickname “the Bulgarian Broadway”. The comparisons to New York City’s Theater District might be slightly ridiculous, of course, but this street truly is the heart and soul of Bulgarian theatre.

Other than theatres, you’ll also find the European Commission’s Bulgarian headquarters on Rakovska. It’s housed in one of Sofia’s more daring examples of modern architecture, bearing an uncanny resemblance to Norman Foster’s Hearst Tower in Manhattan. Funnily, the building is shared with what has to be one of Sofia’s fanciest dental clinics. And on the opposite side of the street, don’t miss the “Sandwiches on Rakovska”, a cult destination for a late-night snack famous for its printsesa sandwiches.

3. Parading with the Count: Graf Ignatiev Street

Parading with the Count: Graf Ignatiev Street
Parading with the Count: Graf Ignatiev Street

Unlike most other Bulgarian cities, Sofia doesn’t have a big car-free city centre, so its few pedestrianized streets are a hub for shops and cafés and a preferred place for weekend walks. That’s exactly the case with Graf Ignatiev Street, colloquially known by everyone as Grafa (“The Count”). Crossing through the Sofia city centre and shared by pedestrians and trams, Grafa connects three important squares. Starting with Garibaldi Square, it continues south to Slaveykov Square with its must-see open-air book market, and then to Popa (“The Priest”), a popular meeting spot. The latter was in fact named after 14th-century Bulgarian Patriarch Euthymius, who was a lot more than just a priest. From his simple monument at the square, though, it seems to be hard to tell.

Since spring 2018, Graf Ignatiev Street has been the subject of a controversial, even infamous renovation, marred by endless delays and questionable construction quality. Since then, the mayor of Sofia, the deputy mayor and the construction company have been the butt of some very appropriate jokes – well deserved for installing “shark fin” bollards on Grafa and thinking a tombstone-like wall of black granite would be a fitting addition to the urban landscape. Still, the authorities’ ill-fated interventions haven’t made Grafa any less beloved – it remains a favourite shopping destination and one of the capital’s landmarks. 

4. Sofia’s nascent arts and crafts district: Shishman Street

Sofia’s nascent arts and crafts district: Shishman Street
Sofia’s nascent arts and crafts district: Shishman Street

It might be a little shabby and run-down, but Shishman (or Tsar Ivan Shishman Street for long) carries a genuine creative energy. Running from Grafa to the National Assembly Square on Tsar Osvoboditel, it’s easy to imagine Shishman as the pedestrianized main street of a hip creative district, much like Kapana in Plovdiv. And this might likely happen in a few years, but for now, its vibe is still totally informal and, one might argue, quite authentic. Funnily enough, the part of Shishman approaching the National Assembly is sometimes called “behind the horse’s tail” – it happens to be just behind the equestrian Monument to the Tsar Liberator. So you know, Shishman is offbeat like that.

Next to the countless little boutiques on Shishman, there’s trendy bookstores like the enchanting Elephant Bookstore too. And with cool bars like Bilkova, Cipy, Kick’s, 5L and One More Bar as well as cute eateries (think HleBar, Takoteka, The Little Things, SupaStar and Skaptoburger), Shishman is a nightlife hotspot for Sofia’s young creatives. And if you’re hungry (or thirsty…) for more, you can always head to Angel Kanchev Street, Shishman’s main “competitor” as one of the capital’s coolest streets.

A little shabby and run-down, Shishman carries a genuine creative energy
A little shabby and run-down, Shishman carries a genuine creative energy

5. See and be seen: Vitosha Boulevard

See and be seen: Vitosha Boulevard
See and be seen: Vitosha Boulevard

If there’s any street that’s the best known in Sofia and most often associated with the city, it has to be the fabulous Vitosha Boulevard, or Vitoshka for short. Sofia’s favourite pedestrian boulevard is swarming with tourists in summer and with locals at the weekend. And while it’s rightfully avoided by those with a more alternative taste, the appeal of its dozens of café and bars is difficult to deny. The gorgeous view towards Vitosha, the imposing mountain in Sofia’s neighborhood, certainly helps with that!

Until a decade ago, Vitoshka was shared by trams and pedestrians in its section between the Sveta Nedelya Church and the National Palace of Culture. Back then, it was almost solely a shopping street and counted as Bulgaria’s most expensive and prestigious avenue. Since a major renovation of questionable quality (sound familiar?) that closed it for vehicular traffic completely, many of the boutiques have given way to restaurants, bars and cafés. Most of those are honest to God tourist traps and clearly overpriced, but remember, on Vitoshka, you’re paying to see (the mountain) and be seen!

6. The Royal Mile: Tsar Osvoboditel Boulevard

The Royal Mile: Tsar Osvoboditel Boulevard
The Royal Mile: Tsar Osvoboditel Boulevard

Sofia overall is way too tattered and unpretentious to be described as “regal” in any way. But on the trademark yellow cobblestones of the stylish Tsar Osvoboditel Boulevard, you could at times feel like you’re in Vienna or Budapest. After all, it’s home to both the former royal palace of the 19th– and 20th– century Bulgarian tsars (now the National Art Gallery) on Battenberg Square and the National Assembly building, where Bulgaria’s parliament meets. Add the monumental façade of the Sofia University rectorate, the sophisticated Military Club, the dignified Academy of Sciences headquarters, the tasteful Italian and Austrian embassies, the Turkish ambassador’s residence and the onion domes of the Russian Church, and you’ve got a whole mix of architectural sights.

Extending from the Neo-Stalinist Largo with the president’s and the prime minister’s offices to the Eagles’ Bridge about a mile to the southeast, Tsar Osvoboditel then continues as Sofia’s widest and busiest boulevard. Past that junction, it’s called Tsarigrad Road, or the “Road to Constantinople“, as it forms the start of the Thrace motorway leading southeast to Plovdiv and the intercontinental megalopolis Istanbul.

7. Shaded bourgeois elegance: Oborishte Street

Shaded bourgeois elegance: Oborishte Street
Shaded bourgeois elegance: Oborishte Street

Oborishte Street is the namesake and main thoroughfare of one of central Sofia’s upscale residential neighborhoods. As it continues east directly from apse of the Alexander Nevsky Cathedral, the capital’s most famous landmark, it turns into a shaded and aristocratic residential street. Fashionable open-air cafés and chic eateries share Oborishte with the Doctors’ Garden, a pleasant little park behind the National Library. On the other side of Oborishte Street are the exquisite buildings hosting the French and Dutch embassies. And in between, just off Oborishte, is perhaps Sofia’s most melancholic ruin – the haunting (if not haunted) House with the Strawberries.

Oborishte, together with the parallel Shipka Street on the other side of the Doctors’ Garden, is one of the streets that has best preserved the charm of Old Sofia as it was before World War II. So if you’ve had it with socialist-time apartment buildings, a stroll around Oborishte and Shipka would provide a refreshing mix of early 20th century architecture.

Fashionable open-air cafés and chic eateries are to be found aplenty on Oborishte and Shipka
Fashionable open-air cafés and chic eateries are to be found aplenty on Oborishte and Shipka

8. Neighbourhood lifeline: Ivan Asen II Street

Neighbourhood lifeline: Ivan Asen II Street
Neighbourhood lifeline: Ivan Asen II Street

Ivan Asen II Street is the backbone of culture and commerce in another of the city’s beloved central neighborhoods, Yavorov. Named after one of medieval Bulgaria’s most successful rulers, the Tsar Ivan Asen II, the street is just as dominant in Yavorov as its namesake was in the 13th-century Balkans (laughable comparison, I know, but I’m almost proud of it). And there’s arguably no other avenue in Sofia that boasts such a grandiose entrance: Ivan Asen II Street’s beginning at Eagles’ Bridge is marked by two almost monumental residential buildings from the 1920s. The appropriately named Asenovets and Tsarevets buildings respectively celebrate the emperor’s dynasty and his birthplace, the royal capital.

In the interior of Yavorov, Ivan Asen II is somewhat less magnificent, but still quite delightful and bustling with life during the day. It’s home to Sofia’s oldest active cinema, the tiny and neglected Vlaykova, and to a myriad of unpretentious restaurants and little shops. Oh, and there’s the Bulgarian Football Union headquarters sandwiched in between.

In the interior of Yavorov, Ivan Asen II is somewhat less magnificent, but still quite delightful and bustling with life
In the interior of Yavorov, Ivan Asen II is somewhat less magnificent, but still quite delightful and bustling with life

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