Sydney’s hip harbourside The Rocks: A journey from criminal to cultural

​Sydney's first settlement has a colourful past and a bright future, writes Tom Adair

Rock star: the area stretches to the Harbour (Getty)

At first glance, The Rocks hides its less than salubrious past beneath a veneer of tourist allure. Sydney's first European settlement, right on the shoreline, flanked by the Harbour Bridge and the Opera House, has been restless since the moment the British First Fleet disgorged its convicts there in 1788 and created the colony that burgeoned into Australia.

This area has always been a shock absorber, withstanding 19th-century notoriety as the heartland of booze and brothels, roamed by ruffians, cops and criminals, then becoming Sydney's booming trade hub with warehouses occupying the waterfront, crawling up and over the hill, creating a nexus of streets and long back alleys.

Sudden wealth threw up the fine buildings you see along George Street, facing the quay. Nearby Sergeant Majors Row, once a workaday terrace, now a listed historic façade, nurtures an ever-changing scene of pop-up artisan shops, interspersed with cafés and galleries. A former butcher's shop (floor tilted to let the blood drain towards the pavement) is now the home of snazzy, eye-catching haute couture.

(Rex)

The whiff of change is unmistakeable. The Museum of Contemporary Art (00 61 2 9245 2400; mca.com.au) has created space for workers on their lunch break to mingle with tourists on the lawn in front of the gallery's new wing, where they can admire or loathe its barefaced modernism, and check out that day's cruise ship, docked where the convicts once pitched their tents.

At the tip of The Rocks, around Walsh Bay, the theatre district, which juts towards the harbour, is a moveable feast of drama, dance and festivity, spilling nightly its noise of theatregoers and drinkers from the wharves straight across the harbour towards the Sydney Opera House.

Yet, just under this surface, The Rocks oozes history. The fingerprints of convicts, along with their signatures in the stone and crumbling brickwork are visible along the Suez Canal (supposedly a pun on “sewers”), but go mostly unnoticed. The Sydney Foreshore Authority aims to bring past and present into joint prominence, adding notes on local history to the walls and pavements, and encouraging new tenants to start up businesses.

Unpack

Set high along tree-lined Kent Street, overlooking Darling Harbour's spectacular sunsets, the three-storey Langham (00 61 2 9256 2222; langhamhotels.com) looks unremarkable from the outside, but on the inside it feels palatial. Reopened late last year after a major renovation, the former Observatory Hotel now has the biggest guest rooms in Sydney, plus a million-dollar collection of paintings by modern Australian masters. Afternoon tea gives way to cocktails and after-dark jazz. Doubles from A$450 (£209), B&B.

Think Local

Sydney's past hides in plain sight. The 90-minute Rocks Walking Tour (00 61 2 9247 6678; rockswalkingtours.com.au; A$25/£12, under 16s A$12/£6) is a poignant exploration of intimate corners of the precinct, from the 200-year-old Cadmans Cottage to Foundation Park, a ruined 19th-century slum. It will also take you along the canal to see the fingerprints of convicts preserved in stone. The Rocks Discovery Museum (00 61 2 9240 8680; rocksdiscoverymuseum.com) in Kendall Lane adds layers of detail, and it's free.

Eat

The Rocks has everything from grab-and-go pancake joints to posh dining, from Asian fusion to Italian, to a grand steakhouse, The Cut (00 61 2 9259 5695; cutbarandgrill.com) in the cellar of a listed heritage woolshed.

The latest hot tip for those in the know is William Blue (00 61 2 9492 3290; williambluedining.com), run by the cream of Sydney's catering college. Crisp linen and high-end decor combine with three courses of Aussie deliciousness (try the rock oysters, roasted pork loin, lamb cutlets or gnocchi), a bargain at A$38 (£18). Just along the street is Le Pain Quotidien (00 61 2 9252 3840; lepainquotidien.com.au), yes, it's the same chain we have in the UK, but this one's in an old police station. Snap your fingers for extra helpings of duck or pork belly, cooked to perfection (A$27/£13) and brought sizzling through the open padlocked iron doors to your in-cell table.

Drink

Where once there were opium smokers and alley thieves, now at night The Rocks reverberates to a beat you can hear all the way from Circular Quay. A cocktail-drinking crowd dances in the courtyard of The Argyle (00 61 2 9247 5500; theargylerocks.com), a cavernous, multi-level space where the DJ is suspended above the dancefloor. Those who prefer to hear themselves think, and each other speak, head to the Lord Nelson brewery hotel (00 61 2 9251 4044; lordnelson.com.au) drinking in the brass and brick surrounds of The Rocks' oldest pub, supping its in-house naval-themed ales: try Victory Bitter or Nelson's Blood.

Shop

Shopping in The Rocks got classier with the recent opening of Joe Bananas (0061 2 8540 0736; joebananas.com.au) on George Street. Past patrons have included Whoopi Goldberg, Stephen Fry and Sir Elton John, and the silk jackets are nothing short of tailored art.

Unmissable too are the opal shops and galleries in Clocktower Square and Metcalfe Arcade. Gannon House gallery (gannonhousegallery.com) has a range of authentic Aboriginal art, while the George Street weekend market offers everything cheap and cheerful, from textiles and plates to key rings.

BridgeClimb (Getty)

Don't miss

From any vantage point, you won't miss the Harbour Bridge. The BridgeClimb experience (00 612 8274 7777; bridgeclimb.com), starts at Cumberland Street. The three-hour standard bridge climb (from A$268/£124) has been augmented by the new shorter BridgeClimb Sampler (from A$158/£73), aimed at climbers in a rush who still want to see the city spread beneath them, with a breeze through their hair, and a souvenir bridge-top photo to prove they did it.

Getting there

Tom Adair flew with Emirates (0844 800 2777; emirates.com), which flies daily from Heathrow, Gatwick, Birmingham, Manchester, Newcastle and Glasgow to Dubai with onward flights to Sydney.

More information

sydney.com

australia.com