the grounds alexandria inner west sydneyThe Grounds of Alexandria

If Sydney’s convicts were still alive they’d live in Newtown, and no one would bat an eyelid. Just left of Sydney’s CBD (in more ways than one) this area has served as a social hothouse for fringe movements from the early 1800s up until today.

In recent years the area has been gentrified by young professionals, so its beautiful crumbling heritage buildings are sandwiched between cleverly renovated warehouses and an emerging restaurant scene that has got food critics talking. Not that Newtown cares much for food critics.

Squatters, migrants, hippies, punks, goths, bums, anti- bureaucrats, outcasts, Trotskyites, protesters and argumentative university students act as a lingering legacy of Sydney’s subversive spirit, and even if you’re not particularly enamoured with veganism, socialism or punk rock, you’ll be hard-pressed to avoid falling in love with the place.

Wake up

The Old Clare Hotel is Sydney’s newest design hotel, housed in an old brewery and pub. Open brickwork, original panelling and some of the cleverest architecture this side of Tokyo are matched by a well-played restaurant game. Ex-Noma sous chef Sam Miller heads Scandi-inspired Silvereye and ex-Momofuku Seiōbo sous chef Clayton Wells is running things at Automata.

Morning

Newtown’s spirit has also spilled outwards into nearby suburbs like Enmore, Chippendale and Alexandria, and it’s the latter you should visit first. Brunch at The Grounds of Alexandria is so popular it’s almost a religion. On weekends the place is full with outdoor food stations, a florist, vegetable gardens, vine-covered private dining spaces and the restaurant itself, which is housed inside a converted pie factory. On your way out be sure to say hi to Kevin Bacon, one of the pigs that lives onsite.

Afternoon

You could spend days exploring King Street. The spine of Newtown streaks outwards from Sydney’s centre, flogging antique jewellery, handmade lace, vintage bicycles, fledging labels, one-off buttons, artisan birdcages, second-hand furniture, tarot card readings, original records and pawn store specials alongside slick global labels like AS Colour. Visit Pentimento for sugar-sweet stationery and get lost in Gould’s Book Arcade, where book-lovers have been worshipping hard-to-find editions since 1967. You might also want a nibble at a slice of Black Star Pastry’s famous strawberry watermelon cake, but save room because you’ve got a lot of eating to do later on.

The south end of King Street presents one of Sydney’s hardest choices: turn left, down the so-called Paris end of King Street, or turn right along the Enmore Road food strip? The best answer is simply to do both. South King Street is the spot to uncover quirky design and homeware stores between creaking old pubs and lively candle-lit tapas bars (The Bach Eatery, created and run by a charming New Zealander, is especially good.)

Evening

Enmore Road is even cosier, with restaurants you’ll want to linger at for hours: book a table at Hartsyard in the months before you arrive (Google #hartsyardsoftie to see why) or show up an hour early at boutique cheese and wine bar The Stinking Bishops to put your name on the list (their no reservations-policy is a blessing in disguise as brewery-cum-bar Young Henrys is just around the corner.)

Make sure you cap off the evening with a scoop of the world’s best gelato at Cow and the Moon – last year they won the Gelato World Tour title in Rimini, Italy and their strawberry balsamic flavour is something else. Alternatively if you’re after something a little harder, move on to Mary’s. People queue for hours to get into this rock’n’roll den, as much for the burgers as the beer. Let’s be honest, there’s always room for a good burger, isn’t there?

The Old Clare Hotel

The Grounds of Alexandria

Pentimento

Gould's Book Arcade

Black Star Pastry

The Bach Eatery

Hartsyard

The Stinking Bishops

Young Henrys

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