HUBS
OXFORD ST
From Whitlam Square, Oxford Square, Taylor Square to 3 Saints Square you'd think we were a bunch of squares. Far from it. Oxford Street is replete with small bars, big bars, gay bars, quirky fashion & retail and great restaurants, cafe's & eateries. It's home to the iconic and very libertarian Stonewall, Colombian, Universal, Oxford & Burdekin Hotels. The food choices are plentiful and there’s something for every taste with cheap’n’cheerful takeaways catering to the lunch crowd, or dinner and a show for later in the evening. Oxford St is the main connector between the city and the Eastern Suburbs, but don't let that put you off, it's always abuzz and its side streets lead to another world.
CROWN ST
Stretches from the Domain all the way down to the edge of Redfern. It's got three main chunks of cool stuff. The northern most is Stanley Street (see below). The southern most is in Surry Hills and well worth a wander down. It's got a very communal vibe, and is a town centre in and of itself - lots of cafes, outdoor dining spots and landmark pubs. But it's the Darlinghurst part of Crown Street that we are interested in here - peppered with small bars, great cheap eats, vintage fashion, books, music and more. Wander along and make some pit stops at the Liverpool St, Oxford St and Campbell St intersections. Make a day of it and have lunch, in the sun, at The Winery.
DARLINGHURST RD
Runs from the world famous Coke Sign to Oxford Street. Well, this aint entirely true, it's also the main drag in King's Cross, but that's King's Cross and we're talking Darlinghurst. This street is pretty cool. It has the Fire Station at the north end, and the fireys are always happy to pose for a picture if they're out front. Govinda's restaurant and cinema is an absolute institution, as is the Darlo Bar. It gets a bit sparse down the south end, running in between the National Art School and St Vincent's hospital, but there is a lovely park there and the Jewish Museum too. Film Club and Radio Alice are here too, next to Robata Grill (worth it!).
VICTORIA ST
Victoria St is going through a transformation right now - just as Covid arrived a few of the bigger restaurants closed shop. But this strip, between William St and Liverpool St is coming alive again, with a handful of artisanal bakeries opening up. And as well as donuts, cakes and coffee they’ve got some great lunchtime offerings too. Messina is across the road, so that’s all 5 food groups covered:) Tropicana Cafe is a great spot to people watch. A luxe grocery store, deluxe florist and a handful of small bars round out the Vic St experience. Turn left onto Liverpool St (heading east) and follow it all the way to Boundary Street where you will find a grouping of some of the best art galleries in the ‘hood.
STANLEY ST
It used to be called Little Italy, now it’s the United Nations of cuisine with food choices to suit every taste and prices for every budget. Whether you’re hankering after an al-fresco snack, a refreshing drink at the bar or a four course meal at one of the many feted restaurants, Stanley St is a prime destination. Of course, Italian is still on the menu and Beppi’s, a Sydney institution, has been serving it up since 1956. Alternatively, Bill+Toni’s $10 pasta deal hits the spot pretty well too. There’s also Spanish at Bar Tapa, Mexican at La Farmacia, French at Bon Vin and Japanese at Stanley St Sushi! New outdoor dining makes this food destination even more fun plus there are five fabulous art galleries to visit as well. (see ART)
LIVERPOOL ST
Liverpool Street runs from Whitlam Square at Hyde Park all the way to Paddington and is the way to 5-Ways Village at Glenmore Road. There are many hotspots with restaurants, vintage & antiques, bars and art galleries all interspersed with vibing inner-city residential houses and flats. It really is an eclectic mix with locals frequenting their neighbouring businesses. There are a few clusters, primarily near the Crown Street end and the Darlinghurst Road intersection. Places of note are the Robin Gibson Gallery, Dedece, the Darlo Bar, Dust Collectibles, Listen Up records (Sat Only) and the hot brunch spot bill’s, plus a whole lot more; are just around the corner and well worth the detour.
WILLIAM ST
William St links Town Hall, via Park Street to the Cross and on to the Eastern Beaches down New South Head road. It's got the newly renovated Australian Museum, the Australian Design Centre and Giftshop and a rather cool little smattering of cafes and eateries, art galleries and other odds and ends. Towards the Coke sign try Grand Days for vintage clothing and books and 1933Boozehouse for live music and cocktails. Keep going over the hill and you will come to Rushcutters Park, a local’s (and dog) haven with harbour views and more coffee options!
FOLEY / BURTON
This little nook is just off Oxford Street and straddles Crown. It's home to unique specialty retail, services owner operated cafe's and two of Sydney's most well known small bars: Shady Pines and Pocket Bar. Foley Lane is also pretty rad to walk up and take pictures of street art and retro Darlo grit. And here, you will also find the Bikram Yoga school.
The corner of Burton and Palmer Streets is a thespian nook with the ESCAC community centre and the Darlinghurst Theatre Company. Round the corner, on Forbes, The Rusty Rabbit and a Brewer’s Tale are local favourites.
CAMPBELL ST
Campbell Street flows from Taylor Square down into China Town. Visit here for more boutique retail and al-fresco eats. It crosses Crown Street so it's very easy to bounce around the two, catching some live reggae and chicken wings at Rosie Campbell's, trying on some retro/vintage threads at the MASSIVE Zoo Emporium, or a new read/vinyl at the Record Store and Oscar’s Books. It gets great light and is a brilliant place to wile away the afternoon. There's also the bottom of Campbell Street which has awesome things like Wild Rover, Harpoon Harry’s $10 Burger deal and Sydney Brewery for craft beers.
TAYLOR SQ / RAINBOW CROSSING
Taylor Square is the centre of East Sydney. It's primarily full of bars: Kinselas, the Courthouse, the Oxford Hotel, Cafe Freda’s, but it's central to everywhere and a great meeting/dropping off spot. The Rainbow Crossing just off the square is idea for a Sydney instagram moment and the smattering of shops and cafes around here warrant an hour or two of exploring. Brix is a rum distillery, upholding Sydney’s dark and colourful past. The Beresford is a great neighbourhood pub with a laid back beer garden and beers, dinners and drag shows. Lumiere Cafe is famed for its massive brunch plates and Veneziano Coffee does a very good brew.
SOUTH DOWLING
Now, this little joint is actually on the cusp of Paddington but it's still very much a Darlo vibe with the Beacham Hotel on the corner and a host of rad little haunts and shoppes leaking back up Sth Dowling towards the Taphouse. There's actually great afternoon light on this street and a couple of very sexy clothing stores, for example Baby Likes to Pony in addition to some very cruisey watering holes. Also, if you see a queue at lunchtime, jump on the end - the locals know what’s what! And bookmark Sth Dowling Sandwiches, Simon Says Juice and Cohab Coffee for good food choices. Sax Fetish and The Bookstore are just around the corner on Oxford St too.