18 Fun and Unusual Things to do in Woolloomooloo, Sydney

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It’s the most fun suburb in Sydney to say, and, while it might not be on the list of the top ten things to do in Sydney – with its local vibe, pretty waterfront setting and iconic pie shop, if you’re looking to explore a bit more of Sydney on your trip, you might want to add it to your sightseeing list. And if you do, here are 17 fun and unusual things to do in Woolloomooloo.

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Where is Woolloomooloo?

It’s just slightly east of the main CBD in Sydney. It’s bounded on the far east side by upmarket Potts Point and the slightly edgier Kings Cross and on the southern side by Darlinghurst.

You can reach it by bus – the 311 goes here from the city – and you can also walk from Kings Cross station in just a few minutes.

Woolloomooloo is also a stop on the Hop On Hop Off Bus that takes in all the main areas of Sydney (check out tickets for that here).

If you prefer walking though, the best way to visit Woolloomooloo – and take in some of the sights in this guide – is to walk through the Botanic Gardens or the Domain and down the steps towards a small road called Lincoln Crescent. From here you’ll see the iconic Finger Wharf building above (which is lined with swanky restaurants) and can head out onto the rest of the suburb.

There’s also a pedestrian bridge just by the Big Matchsticks, below (look for the green line on google maps) that will bring you out into Bourke Street. This way isn’t quite as pretty as the other way though.

Because you’ll be walking past them, we’ll also include a few sights in and around the Domain for you to check out. After all this is Differentville, boundaries mean nothing to us (and these things are cool so I’m adding them!)

So, let’s get started,,, with one of those exceptions.

Fun and Unusual Things to do in Woolloomooloo

1. The Big Matchsticks

Located on a patch of land just behind the Art Gallery of New South Wales (a must-visit if you like art), these are not, technically, one of Australia’s iconic big things, but instead a piece of art by famed local artist Brett Whiteley.

sculpture or two giant matchsticks on a hill in Sydney

The Matchsticks are 8 metres high and their official name is Almost Once.

Apparently, they represent the idea of living life to its fullest until you finally burn out. Somewhat ironically, the sculpture was completed a year before Whiteley died from a drug overdose.

The local cockatoos, obviously have no sense of art or history and have decided that the matchsticks make brilliant chewing posts so, they do have to be restored every now and again!

If you want to learn more about Brett Whiteley – check out this post on the garden dedicated to him in North Sydney. It’s quite the tragic story.

There’s also a number of books about him, but Brett Whiteley: Art, Life and the Other Thing by Ashleigh Wilson is the authorised biography to check out. Click here to order it to read on your trip – or see reviews.

.2. Eat Sydney’s Most Iconic Pie

The pies at Harry’s Cafe de Wheels have been sampled by everyone from Elton John to Joe Jonas and, while they now have a couple of locations around the city, the Woolloomooloo one is the original.

And the one with the prettiest view!

It’s located right on the water on the Cowper Wharf Roadway

Grab a plain pie or go for the classic Tiger Pie which topped with mashed potato, peas and gravy. Perch on one of the limited seats – or balance it on your knee with a view of the warships and experience a piece of Sydney history and one of it’s most iconic foods.

Plus it’s a bargain at under $10 for a pie. There’s not many meals under $10 in Sydney!

3. Get Your Vegan on at Alibi

Not keen on the concept of munching cow wrapped in pastry sitting by the side of the road, then get your glad rags on and head off for a posh vegan dinner at the Alibi restaurant at the Ovolo Hotel.

The chefs at Alibi are seriously creative – when I went,they served a dehydrated watermelon poke dish that blew my mind.

Looking at the menu today, there’s choices like a mushroom-stuffed Yorkshire pudding and kimchi dumplings to choose from.

You can order dishes individually or let them choose for you and try the 8-course degustation menu. You won’t be disappointed.

They also do a Vegan High Tea.

Here’s where to check out the menus or make a booking.

4. Or at Least Meet The Gnomes

The Ovolo hotel group pride themselves on doing things a bit differently and one such touch is the gnome they use to reserve your table in their in-house bar,

Look, how can you not love him!

You’ll have to have a table booked to make use of him but, considering these are the type of cocktails you’ll find at the bar, why wouldn’t you want to do that?

5. Snap a Purple Picture

If you’re in Sydney in late October/early November, you’re likely to hit jacaranda season, and if you do, Woolloomooloo has a couple of great locations for pictures.

Most notably, Cathedral Street close to the junction with Dowling Street which lets you get this shot with the Sydney Tower Eye in the background.

If you want more purple pictures during your stay, check out this post on some of Sydney’s other iconic Jacaranda locations.

6. Head into Artspace

You could easily walk past this Art Gallery on Cowper Wharf Road if you didn’t know it was there, but don’t.

The two-floor space won’t take long to cover, but the exhibitions change regularly and there’s always something a bit surprising to see.

You can check what’s on here, or just wander in. Entrance is free after all.

7. Grab the Prettiest Cakes at Petal Met Sugar

This florist and bakery combo cater mostly for weddings, but they have a small onsite bakery and cafe with some of the prettiest cakes in Sydney.

They also do a high tea at weekends.

You’ll find them at Shop 7, 68 Sir John Young Cr. It’s a small space so be patient – and, if you want to try the high tea bookings are essential. They’re only open in the mornings. Check their website for exact hours and to make a booking.

8. Get Social at Contact Bar

When this place first opened it made its name by asking people to lock their phones away in a box so you’d actually talk to your fellow diners (remember doing that).

Apparently, they no longer do this, but it’s still a very cute place to drink or dine.

Order a la carte from the varied menu which swings from Brisket Burgers to Squid Ink Spaghetti or, check if they are running their secret degustation menu where only the chef knows what you’re going to get.

You’ll find them at 80 Crown Street. For more details or to make a booking, visit their website.

9. Have a Swim and a Sunbathe

This is another one of those sights that’s not technically in Woolloomooloo, but overlooks it, so I’m going with it.

Andrew Boy Charlton pool is located on the cliffs close to the domain and it has a view of the water, Woolloomooloo and the battleships that dock at Garden Island.

It’s also one of the best places in the Sydney CBD to swim and sunbathe.

It gets extremely busy at weekends so, try and time your trip in the week if you can.

Oh, and the pool is salt… that totally surprised me when I swam there.

For all the details, check out this post on Differentville’s sister health blog.

10. Listen to the Sound Sculptures

Even if you don’t want to swim, you should head toward the pool as in the water nearby is a set of sculptures called Dual Nature by artist Nigel Helyer.

They’re supposed to represent ships launching to tie in with the maritime history of Garden Island (where you see the big grey battleships opposite). You’ll find a full description of the sculptures from the artist himself here.

What’s most cool about them though is that they make noise. As the water from the tide goes in and out the sculptures reverberate.

11. Check out the Cute Eggs at Flour and Stone

One of Sydney’s most popular cafes, they earn their place on this list purely because they cover their boiled eggs with the cutest knitted covers.

Sadly, I can’t take a photo of the adorableness right now as it takes place in the part of the cafe called the Salon which is currently only open on Saturdays due to you know what! And oh heavens, the queue!!!

They also do super adorable cookies. Those you can get seven days a week.

Find them at 43 Riley Street.

If you like what you taste, Flour and Stone also do a cookbook. Check it out here.

12. Take the Razorhurst Tour

While the chi chi surroundings of the waterfront might lead you to believe that Wooloomooloo is all new and shiny, as you go inland, it’s a different story.

You’ll find row after row of tiny terraced houses, and while today these have super high price tags, back in the 1920s, Woolloomooloo, Kings Cross, Potts Point, Darlinghurst – and nearby Surry Hills, were notorious for crime, illegal booze dens, prostitution and violence.

They were known as the Razorhurst gangs, because of their pleasant habit of cutting their rivals’ faces with razors. Interestingly, two of the most notorious criminals of the time were women – brothel-keeper Tilly Devine and illegal booze peddler Kate Leigh.

You can download a map of the main locations, including the then infamous, now quite nice East Sydney Hotel, at Razorhurst.com.

If you want to read more about the history of this era before you come, also check out The Law of the Razor by Larry Writer which covers the era in detail.

Also note, while the violence of the Razorhurst gangs might have passed, Woolloomooloo does still have a few social issues and while it’s still very safe in comparison to what you might find in many other cities in the world, do just keep your wits about you if you start wandering the backstreets. I also keep mostly to the main roads at night.

13. Hit the Pub

Talking of pubs… there’s a lot of them in Woolloomooloo.

My first choice is the Woolloomooloo Bay Hotel; it’s down to earth but not too shabby – and the tables on the balcony have a nice view of the water.

Next to this is The Bells, it’s, let’s say, an unfussy pub, and, rumoured to be a drinking hole of actor Russell Crowe who has an apartment in the swanky Cowper Wharf building opposite. Probably because no-one in here will give two figs who he is!

The Tilbury is where the bright and the beautiful go – especially on a Sunday afternoon.

The Frisco is another good choice. It has a few outdoor tables and a really nice feel about it. I don’t go here as often as I probably should!

Lastly, there’s the Old Fitzroy Hotel, which is a right mix of characters. Regulars include playwright Louis Nowra and he immortalised the pub – and the local area in his book Woolloomooloo.

If you love reading books about where you’re travelling to, you’re going to want to pick this one up. It’ll either make the pub the first stop on your trip, or send you running for the hills in the opposite direction.

They also have a tiny theatre attached if you want to get cultural as one of your fun things to do in Woolloomooloo.

14. Find the Woolloomooloo Sign

How many times can you walk past something and not see it? About six seems to be the answer, at least when it comes to the Woolloomooloo sign at least!

I had seen pictures of it, but wasn’t quite sure where it was – and the fact that as you walk towards it, it’s hidden by a massive plant does not help!

If you want to find it though, it’s in the middle of the road by the junction of Palmer and Cathedral Street.

Behind it is a small garden with metal cows and sheep. This was created by a TV show called Guerilla Gardens. They were also responsible for the Sydney Troll.

15.Tour the Museum of Magic

Technically, Woolloomooloo ends at a road called William Street and this is just across that and in Darlinghurst, but it’s really good fun so whose counting!

The evening tour teaches you the secrets of all those magic tricks you were amazed by when you were little.

See more about it in this post.

16. Spot the Fake Doors

These doors on the back of the Elephant Backpackers on Crown Street look real, but they’re actually painted on.

Nope, I have no clue either but it’s just one of the odd little touches you spot around here.

A house over the road from here has a sculpture of brightly coloured pencils in its front garden, and, if you wander past the ballet school on at the right time of day you’ll be treated to the site of girls en pointe practising in what looks like garage while their mums look proudly on!

17. Find the Fintan Magee

There’s a few pieces of street art in Woolloomooloo, although not as many as you might expect considering it’s one of the grittier parts of Sydney.

One piece you might want to seek out though is Support by Fintan Magee on the wall of the Plunkett Street School.

Because it’s on school property it’s a bit tricky to get a decent picture of it. This was the closest I could manage and it involved shoving my arm through the bars of a gate – loving the additional bin detail!

Otherwise you’ll find some interesting historical murals in Bourke Street under the flyover – there’s also some vibrant tag themed art here.

The walls of the basketball courts and Woolloomooloo Playground are covered with bright murals and you’ll find some indigenous art-themed pieces at the junction of McElhone and Sydney Place.

Also, look out for this mosaic work on the PCYC building on the corner of Riley Street. It’s by famous Australian artist Byram Mansell.

18. Go Down the Rabbit Hole at Peekaboo Bar

Described as where Alice in Wonderland would drink if she ended up in Sydney, this tiny bar on Bourke Street looks like it belongs back in those Tilly Devine days (without the nasty bits!).

It’s the perfect place to finish your day of exploring in Woolloomooloo and I can firmly recommend the pretty Bourke Street Sour which is a layered mix of whiskey with lemon, red wine and egg white!

Mr Differentville got lured by the word Cointreau and had a Boops Pash – the cinnamon ring round the rim makes it taste like Christmas!

Where to Stay in Woolloomooloo

The Ovolo Hotel: It’s the chicest place to stay in Woolloomooloo. I’ve already talked about the fantastic bar and restaurant – but I haven’t mentioned the lovely water views. It’s located in the Finger Wharf building and so many of the rooms have direct views over the water

Click here to see rates and availability.

Mariners Court: If you’re looking for something a bit more moderately priced, then check out the Mariners Court Hotel.

As you can see, the outside is a bit strange, but inside is a different story and each room is slightly different in the way that it’s decorated.

I gets rave reviews on booking.com for its friendly service and some of the rooms open out onto a cute courtyard or have a balcony.

Click here to see pictures of the rooms -and the reviews and prices.

Airbnb: When I stayed in Woolloomooloo I stayed in an Airbnb in the Finger Wharf building which had the most amazing waterfront views. That apartment seems to be off the platform, but this one is very similar (and cheaper than the hotel – shhh)

If you’re looking for something else, here’s what else is on offer nearby.

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So, there you have it. My guide to some of the more fun and unusual things to do in Woolloomooloo. If you like it, please share it on social media so other people can find some fun things in the suburb too.

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