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Town Hall Square is a popular gathering spot for Tallinn’s tourists and local alike.Amy Laughinghouse

Tallinn is making up for lost time. Having endured a Nazi invasion and decades of Soviet rule before gaining independence 22 years ago, the Estonian capital is still very much like a freshman at university, relishing a taste of freedom, revved up on Red Bull and ready to party.

And yet, wherever you go, history smacks you on the back of the head like an ill-advised shot of Jagermeister. Remnants of the past are juxtaposed against a kind of frenetic, youthful joy and capitalist ambition. If you want to experience a society at a cultural and temporal crossroad, visit Tallinn.

The allure of Old Town

For most visitors, the main year-round attraction is the medieval Old Town.

This pedestrian-friendly core is partly framed by turreted city walls, which embrace a maze of cobblestone streets and a Town Hall flanked by cafés and handicraft shops.

A 16th-century stone tower still stands atop Toompea ("Castle Hill"), while a heavily ornamented, onion-domed Orthodox cathedral from the late 19th-century presides over a square nearby.

For an old-fashioned feast, sit down for a meal of bear, wild boar and elk at Olde Hansa, which is kitted out with iron candelabras, tapestries and minstrels playing in a gallery.

If it proves too rich, head over to the Raeapteek Apothecary Museum on the Town Hall Square: Among disturbing displays of jarred toads, burnt hedgehog and dried deer penises – all of which have far surpassed their "use-by" date – you'll find modern medicines and wrinkle-reducing creams for sale.

After dark, the Old Town pulsates with an eclectic nightlife. Hipsters groove to wax-spun tunes from the 1950s, '60s and '70s at Kohvik Must Puudel (Black Poodle Café), a basement dive outfitted with retro furnishings, while a few blocks away at Club Privé, men in black leather dance atop glass platforms while girls in skimpy "police" uniforms distribute shots.

The struggle for independence

Even in the midst of 21st-century excess, reminders of Tallinn's oppressive past remain. At the Rotermanni Vanakraamiturg flea market, where daylight filters dimly through dusty windows, visitors are greeted by the usual assortment of antique castoffs: battered trunks, a rocking horse, fringed lampshades. But strange objects lurk in the murky recesses.

A painting of Joseph Stalin. A doll in a baby carriage, its face obscured by a gas mask. A shadow box featuring a poignant display of bullet casings, a rusty bayonet and a multitude of medals – a memorial for a fallen soldier, perhaps? It's a warehouse of Estonian history.

For a more official collection of artifacts, check out the Museum of Occupations at the base of Toompea. It is filled with relics from the Nazi and Soviet regimes, including larger-than-life statues of former leaders, bullet-riddled objects from slain resistance forces, and a coffin-sized closet where suspects were holed up for hours prior to interrogation.

The TV tower on Tallinn's outskirts, which provides 360-degree views over the city from 170 metres up, is perhaps the most visible symbol of

Estonia's struggle for independence.

Mati Rumessen, who offers tours of the city, was one of the protesters who prevented Soviet troops from shutting down this vital means of information

distribution on Aug. 19, 1991.

"I could have been shot," he says. Fortunately, the soldiers were ordered to stand down, and the Soviet Union fell later that year.

The rocky road to capitalism

Today, Tallinn's economy is based mostly on finance and Internet technology.

It was the birthplace of Skype and the first country to offer national online voting for local elections; a pilot program is teaching computer coding to schoolchildren as young as seven. Still, the average monthly income remains just €887 ($1,200) a month, compared with nearly €3,109 in Finland, where many Estonians seek work to make ends meet.

"We call the ferries to Finland 'slave ships,'" Rumessen notes wryly.

Things are improving. Many of the distinctive clapboard houses in the streets near the KUMU Estonian art museum, opened in Kadriorg Park in 2006, have been restored.

In the Rotermann Quarter, a revitalized neighbourhood

colonized by cafés, restaurants and fashionable clothing shops, glass and steel structures are springing up around 19th-century warehouses, a physical

manifestation of Tallinn's efforts to assume its place in the modern era without obliterating its past.

The most obvious display of the city's entry into capitalist society is the gleaming banks, offices and hotels that tower over the Maakri district.

Swissotel Tallinn is the tallest of them all, a smoked glass monolith that dwarfs its neighbours. Inside, the tailored decor – the vision of an Estonian designer – features dark wood and copper-coloured glass tile accents.

The highlight is found at the 30th-floor restaurant. Beyond the crystal chandeliers and gossamer curtains, the view extends towards the red-tiled roofs of Old Town, hunkered down beyond jagged highrises that have sprung up like an artificial mountain range bisecting the city.

Tallinn is a marvellous, quirky mix of crumbling communism and fledgling capitalism – a rare glimpse of a young nation finding its footing. Will it succeed? Cross your fingers and hope for the best, but book your tickets now.


Getting there

Connecting flights to Tallinn are available through a number of cities, including Amsterdam and Frankfurt.

Where to eat and drink

Olde Hansa: Where else can you wash down marinated bear with a mug of cinnamon beer the size of your head? Vana Turg 1,

Kohvik Must Puudel: Old beatniks never die. They're reincarnated as cool kids at this eatery, a.k.a. hipster nirvana. Muurivahe 20

Club Privé: This is one of the best nightclubs in town – assuming you can handle crowds and really loud dance music. Harju 6,

Where to stay

Swissotel Tallinn: Amenities include a cigar lounge, spa with an indoor pool, car services, child care and 24-hour concierge. Rooms from about €125 ($170). Tornimae Street 3,

The writer's trip was subsidized by Swissotel Tallinn. The hotel did not review or approve this article.

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