In partnership with 
Overview
With all these blustery, grey, wintry days afoot, you'd think Sydney would begrudgingly hibernate for the season, retreating indoors to binge-watch Cleverman and inhale a bunch of soup. But the city's got too much going on, too many new exhibitions opening, activities aplenty and hidden natural gems to explore.
Bundle up in your favourite woolies and get amongst your city this chilly season. All you need is a crisp $20 — and in most of these cases, you'll have a little (or a lot) left over.
By the Concrete Playground team.
1. EAT HOUSE-MADE DAMPER IN A CITY PUB
Redesigned by the team behind Momofuku Seiobo and Bar Brose, and with a menu inspired by the pub's former regular Henry Lawson, The Edinburgh Castle has officially reopened in the CBD. Ex-North Bondi Fish chef Daniel Lanza has created a menu that subtly references the Edinburgh's important literary history as one-time home to Aussie writer and poet Henry Lawson. Tasty morsels on the snacks list include house-made damper with garlic herb butter ($8 a serve), the perfect thing for a chilly winter's day. They also do a mean pork sausage roll for $14.
Cost: $8
2. BUNDLE UP AND TAKE A HIKE
According to the ancient Greek physician Hippocrates, 'walking is man's best medicine'. 2500 years — and the invention of antibiotics — later, he's still got a point. This week, a Tasmanian study showed that people in their 50s who walk 10,000 steps a day, every day, lower their mortality risk by 46%. And in Sydney — where spectacular waterfalls, mountains, caves and coastline are just minutes away from the car-strangled CBD — following the doctor's advice is easy. Plus, you'll boost your overall health to avoid those nasty winter sniffles — just make sure you bundle up and take your vitamins.
Cost: Free
3. VISIT THE CALYX
Meet the Royal Botanic Garden's new world-class horticultural experience, The Calyx. Opened 200 years after the official opening date of the Garden on June 13, 1816, this dazzling new UFO-shaped public space not only houses thousands and thousands of plants, but gives Sydneysiders an escape from the city's busy streets and relentless traffic. It also provides a new home for fun, innovative exhibitions. The first, now open, is Sweet Addiction, the botanic story of chocolate, from bean to bar. Also part of the show is a collection of over 18,000 plants, which are arranged as living artworks. Together, they form the biggest interior green wall in the Southern Hemisphere, measuring six metres in height and 285 square metres in area.
Cost: $15 online/$17.50 at the door
4. FIND OUT WHAT IT MEANS TO BE 'POST-HUMAN'
Step into New Romance: art and the posthuman at the MCA this winter and you'll be greeted with a dizzying array of moving parts, flickering lights and a casual spot of time travel. Splicing science and technology with politics and aesthetics, 18 artists from Australia and Korea conceive of the distant and not too distant future in this just-opened exhibition. New Romance runs Thursday, June 30 to Sunday, September 4 at the Museum of Contemporary Art and is open until 9pm on Thursday nights.
Cost: Free
5. 'RESEARCH' YOUR WAY THROUGH SYDNEY'S BEST BAKERIES
Sydney bakeries these days are in hot competition for your dough — especially in winter, when fresh, hot, bready goodness is just the ticket for a dreary day. There aren't many bakeries left just churning out simple loaves of white bread — now it's all about sourdough, fruit loaves, croissants, cronuts and cruffins. But not all of them rise to the occasion, so we're here to sort out which establishments you knead to visit, and which crumby ones you can be gluten-free of. Use your loaf and follow the Concrete Playground Crust-See Sydney Bakery list this season.
Cost: Around $5-10 per visit
6. LEARN UP ON FRIDA KAHLO
Two of the greatest artists in history, who happened to have one of the most volatile relationships in recent memory, are the focus of the Art Gallery of New South Wales' brand new exhibition, Frida Kahlo and Diego Rivera. Kahlo and Rivera's artistic and personal rollercoaster ride is the focus, with 33 artworks from the pair — including self-portrait paintings, drawings and canvases — all from the renowned collection of Jacques and Natasha Gelman. Australia doesn't actually have a Frida Kahlo on public display, so this is one heck of a slam dunk for the gallery.
Cost: $14-18
7. CURL UP NEXT TO A FIREPLACE
As the pelting rain and wind of winter roll in, it's easy to see your enthusiasm for a night on the town being replaced by a deep craving to don your long dachshund-print pajamas and settle in for a dry and drama-less night of MasterChef. But there's one thing we know that's worth braving the rain and wind for, and that's cosy beers at one of Sydney's fireplace-equipped pubs and bars. It's your chance to feel like Hemingway with an alcoholic beverage in one hand as you relax in a room filled with that incredible open fire. Here are nine of the best.
Cost: Around $10 for a cheeky beverage by the fire
8. WANDER THROUGH A BAMBOO PAVILION
Paddington's Sherman Contemporary Art Foundation is going green with the final installation in their Fugitive Structures temporary pavilion series. For the finale of this awesome series, SCAF has teamed up with award-winning architect Vo Trong Nghia to create Green Ladder. The pavilion structure is made entirely from bamboo, "the steel of the 21st century" according to Nghia. The temporary pavilion will be on public display at SCAF from July 7 to December 10 and aims to raise awareness of bamboo's strength as a 'green steel' building material. Green Ladder aims to resemble a dense bamboo forest and visitors will be able to move through the graceful grid at their leisure.
Cost: Free
9. GO ROUND THE TWIST AT SYDNEY'S LIGHTHOUSES
Gone are the days when lighthouses were the domain of lonesome keepers, spending long nights keeping an eye on kerosene lamps and braving the fog and the foam. These days, automation does all the work. But despite that, it's hard to spend time at one without feeling like you're going back in time 100 years, when adventuring by ship was an extraordinarily risky business. Since 1622, more than 8000 ships have wrecked on the Australian coast, yet only about 2000 have been found. Visit these ten lighthouses in and around Sydney to travel back in time a little, take in some dazzling views, visit some beautiful beaches and perhaps even sleepover in an original light keeper's cottage.
Cost: Free
10. SEE A SEASHORE ART EXHIBITION YOU'D USUALLY SEE IN SUMMER
Lovers of outdoor sculpture, you no longer have to wait till October for your waterfront fix. The good folks at Sculpture by the Sea are teaming up with the Barangaroo Delivery Authority for an epic new annual exhibition, Sculpture at Barangaroo. Launching on August 6, the inaugural event will feature 12 spectacular outdoor works, created by fifteen Australian artists. Six of the pieces are brand new, while the other six are existent, but have been handpicked for their suitability to the site. Best bit? It's free.
Cost: Free
11. DO YOGA AT AN URBAN FARM
Though Sydney is filled with some awesome yoga studios, there are very few chances for city slickin' yogis to breathe in fresh air while trying out their best crane pose. Pocket City Farms is connecting mind and body to the actual earth with outdoor yoga classes that overlook their urban farm. For those worried about the winter chill, the practice will be held in a heated pavilion overlooking the market garden, with additional heaters and clear blinds also available for the cooler mornings.
Cost: From $10
12. GO WHALE WATCHING
Whale watching season is upon us, and the New South Wales coast is one of the best spots in the world to catch these majestic creatures in action. From May to November, the Pacific Coast migration goes from south to north and back again as the whales seek warmer water for the winter months. While humpbacks are the most documented, you might be lucky enough to catch orcas, brydes and southern right whales as well — and all without having to step foot from dry land. From Sydney to Byron, we've put together a list of all the best spots to stake-out and catch a glimpse of the majestic sea creatures. Binoculars, hiking shoes, snacks and picnic blankets recommended.
Cost: Free
13. TRY A POPCORN OLD FASHIONED
Easy Eight was opened by the Mojo Record Bar crew in March 2016 and they've got one heck of a delightfully fun winter cocktail for you. Order big from the fun and frivolous cocktails list, where every drink comes with an edible garnish, hurrah! There's an apple pie cocktail (i.e. an appletini) with an adorable pie crust lid which you can pull off and dunk into your drink. But we're here for the Popcorn Old Fashioned, with popcorn-infused bourbon, maple syrup and little pieces of popcorn. It'll warm you right up.
Cost: $19
14. EXPLORE HIDDEN CAVES NEAR SYDNEY
Don't spend all winter sprawled on the couch enthralled by The Goonies — go out and choose your own adventure. Within a couple of hours' drive of Sydney, there are hidden caves for cooling off in, huge sandstone caves for camping in (with 50 or so of your closest mates), beachside caves for picnicking in, tunnel caves for meeting glow worms in and river caves for swimming in. In short, there's a lot of caves. Here are ten we think you should visit.
Cost: Free
15. SNUGGLE UP TO SOMEONE ELSE'S DOG
Dog-sharing. Yep. Read it again. Dog-sharing. Services that allow pooch owners to connect with other pooch owners to help with everyday care, pupsit for holidays, do walks and so on. It's happening. Australian service Dogshare was initially launched for dog owners only, but it's now launched a pretty damn exciting feature — a 'borrowing' feature for dog loving people in the same neighbourhood. Similar Aussie service BorrowMyPooch works on the same principle but has a subscription fee for owners and borrowers, while Pawshake is free to sign up as a sitter, but owners pay to host their pups.
Cost: Free
16. BUY A SUCCULENT
The gardening bug is a hard one to shake. What might start off as some Woolies parsley growing in the windowsill above the sink can quickly evolve into obsessively spraying Seasol on your asters and getting elbow-deep in dirt to dig up this month's potato harvest. By then, you'll know succulents are glorious gems to invest in during the colder months — they're hardy little blighters. Here are the ten best places to buy plants in Sydney, go pick out a nice little summery cactus.
Cost: Smaller succulents can cost as little as $10
17. BRAVE THE COLD AND LISTEN TO THE STARS SING
It's such a shame David Bowie's not around to see this. Sydney installation artist Michaela Gleave has come up with an app that translates constellations into musical scores so you can 'play' the stars above you. Wherever you are in the world, at anytime of night, A Galaxy of Suns can read your geolocation and plays the music it transcribes from the constellations within your view. Bundle up and get amongst the cold winter night.
Cost: Free
18. FIND HIDDEN ARTWORKS IN THE CITY
If you've got a hankering to see new art but have run out of vital organs to sell for travel money to Venice, there's actually quite a bit to see around the traps. You can experience a whole different cultural side to Sydney, especially in the CBD, if you know where to look. Check out our guide to some of the best public art permanently installed by the City of Sydney — you might have literally tripped over it.
Cost: Free
19. GO BUSHWALKING IN THE BLUE MOUNTAINS
If you particularly love a solid mountain trek in winter, pull on those Blundstones. We're lucky enough to have so many great hiking tracks right in our backyard, and the best among these is arguably the Blue Mountains, but with so many trails and paths to traipse, choosing is the hard part. From easy day hikes to hardcore overnighters, the Blue Mountains have it all. Check out a few of our favourites.
Cost: Free
20. GO FOR A BIG LONG BIKE RIDE
Many people associate cycling in Sydney with dodging cars, battling road rage and navigating their way through complicated tangles of main roads and side streets. But it's the best way to warm up with the wind in your hair this winter, and there are oodles of dedicated (and more serene) bike paths to explore, passing through expansive parks, around tranquil lagoons and alongside stunning beaches. Whether you're still on your training wheels or prepping for the Tour de France, here are ten of Sydney's best bike routes.
Cost: Free
Top image: Ondrej Supitar.