Paul Sullivan eschews Tallinn’s “chocolate box” center and explores its rougher, but arguably more fascinating outskirts…

Much has been made of Estonia’s speedy and successful transition from oppressed Soviet satellite to free-thinking member of the European Union.

But while its capital does carry a modern, progressive air – lots of pleasant cafes and restaurants, free wifi everywhere, friendly people – the scars of its Soviet (and prior) past are not only clearly visible but give the city an appealingly gritty edge.

In most contemporary travel reports, these industrialised and Soviet aspects of the city are airbrushed out in favour of the thoroughly restored Old Town. Search Google for images of Estonia’s capital and you’ll mostly find pretty pictures of the central skylines pierced with soaring church spires, wide angle views of cobbled lanes and the unarguably impressive displays of medieval towers.

But the city’s less polished past is everywhere you look. Former industrial areas like the Rotermann Quarter have been successfully transformed into upmarket offices and luxury apartments; the harbour still hosts the former Tallinn Electricity Plant (whose vertiginous chimney dominates the view) and the concrete Linnahall concert hall and sports venue (previously known as V. I. Lenin Palace of Culture and Sport), which was built for the 1980 Moscow Olympics; and ringing the city center are plenty more nods to Soviet architecture in the shape of more abandoned buildings and communist tower-blocks, not least in the Russian enclave of Lasnamäe.

Things get rougher – and even more fascinating – the further out of the city you go. The trendy North-Western district of Kalamaja, formerly a fishing village, is a muddle of pre-Soviet wooden houses and abandoned factories. Imagine if Stalin had run Reykjavik for a few decades and you’ll get the overall aesthetic.

Telliskivi, the mini-district between the central railway station (itself an interesting time-warp) and Kopli freight train depot, has become a self-appointed Creative City, hosting hip cafes like F-Hoone and other arts and cultural centers.

Locals told me that around 15 years ago, Kalamaja was quite dangerous – “Tallinn’s Bronx” as someone put it, without any apparent trace of irony. It’s true that drunks and homeless folk still mingle with the young creatives and elderly residents today, though it’s further north in the suburb of Kopli that you’ll find a much less gentrified state of affairs.

Here, the meld of post-war estates and 19th century wooden houses are even more dilapidated. Groups of drunks gather at bus stops (another local told me that vodka abuse still kills the majority of Estonian men off before they hit 60), and though I wouldn’t say it felt dangerous, some of the stares definitely made me feel uncomfortable. Yet right at the northern tip, the shanty-towns and concrete communities suddenly give way to splendorous views of the coastline that reach right across to the central harbour.

The images below reflect my 10km urban hike from the centre to the very tip of the north-west, and my quest to capture the less polished – but no less charming – aspects of a city that’s mostly still very much in flux…