Your Guide to the Sydney Long Weekend

That gloom-less Sunday afternoon vibe, that triple-header sleep-in, that victorious pyjamas-only Monday. The long weekend is upon us and if you think you're going to spend it catching up on understandably excellent episodes of BoJack Horseman, there's too much balmy air and tasty events in Sydney to even consider bunking in.

Dig into the hearty, hearty deliciousness that is Good Food Month, then there's two free carpark gigs, entire festivals dedicated to cider and chocolate and one heck of a sharply dressed birthday party. Perhaps you're making the roadie to Newcastle for the National Young Writers Festival to fill your brain with sweet knowledge and creativity. Newcastle's underrated, you should visit One Penny Black for pourovers or The Edwards for cheesy fries. Just do it.

We've broken it down for you, the best things to do in Sydney over the long weekend. Take your pick of Saturday, Sunday and Monday's best around-town nosh pop-ups, parties and live gigs — you've plenty of time to nurse that fuzzy bear head in time to drift back to work on Tuesday.

Get amongst it.

SATURDAY

Junkyard Festival at the Vic

It's starting to feel like every weekend one of our favourite inner-west music havens, Vic on the Park, is hosting one must-attend event or another. Not that we're complaining. On Saturday, October 4 it's the Junkyard Festival at the Vic. The Junkyard Festival is held bimonthly in Sydney's inner west, showcasing some pretty sweet local music. The lineup sees a string of local favourites such as Deep Sea Arcade, Chicks Who Love Guns, The Upskirts, Doc Holiday Takes the Shotgun and Grease Arrestor playing in the Vic's beloved carpark. Supplementing all this live music goodness, the crew have also got some solid DJ action going on in the form of Palms, Tsars, Zero Likes, Ok Cocaine, Bachelor Pad, Bust Lip and Simbles. Entry is completely free, however RSVPs are encouraged. Drinks are recommended.

Saturday, The Vic on the Park.

The Festival of Chocolate

How has this not been done before? Over Saturday and Sunday, you'll feel like a kid in a candy store. The two-day Festival of Chocolate will see The Rocks transformed into a sea of market stalls, as dessert chefs from all over the country try to win you over with an array of chocolate-inspired concoctions in every mouth-watering form possible. 2014 is the debut of this festival, featuring as part of Good Food Month. Though some of what we might think of as the big guns of Australian dessert are staying home for this one, Rocks residents Ananas Brasserie, Baroque Patisserie, Bar 100 and La Renaissance will be spruiking their tasty, melty wares, alongside wider NSW choco-talent Sweetness the Patisserie, Chocolarts, Le Pain Quotidien, Adora Handmade Chocolates and Danieli's Fine Foods. Watch the people who have dedicated their life's work to making chocolate — heroes, really — demonstrate on the Chocolate HQ stage.

Saturday and Sunday, The Rocks.

Louder than Words - Sydney Dance Company

Expect to see the human body pushed to its absolute limits, choreography that seems almost miraculous and a potent blending of music, poetry, costuming and design.This exclusive Sydney season, Louder Than Words, is bringing two of the most awe-inspiring dance works (ever!) to the Sydney Dance Company stage. And they're both world premieres. From SDC artistic director, Rafael Bonachela, there's Scattered Rhymes, which is a collaboration with Australian composer Nick Wales and Grammy-nominated British composer Tarik O'Regan. Then, from Greek choreographer Andonis Foniadakis, there's Parenthesis, which features an original score written by French composer Julien Tarride and costumes created by fashion designer-photographer Tassos Sofroniou.

Kicks off Saturday, Sydney Theatre, Walsh Bay.

National Young Writers Festival

National Young Writers' Festival (NYWF) is the four-day writerly celebration that takes over the imaginations of young writers around the country. Directors Alexandra Neill, Jessica Alice and Lex Hirst's colourful program features familiar names like Benjamin Law, Yassmin Abdel-Magied, Clementine Ford, Lawrence Leung, Genevieve Fricker, Steph Harmon, James Colley, Patrick Lenton and more (including some other names you might not recognise now but definitely will in the next five years). Blowing out 17 candles this year in Newcastle, NYWF is growing bigger and wiser by the year. But a festival is never too old for an intergalactic-themed ball and a spelling bee-cross-Hunger Games-style battle of the brains, right?

Thursday to Sunday, Newcastle.

The Shiny, Newly-Reopened Manly Wine

Seaside wine is pure textbook How to Long Weekend stuff. Reopening its doors following the first renovation since opening in 2009, Manly Wine is back with a clean slate ripe for the long weekending. Unveiling a brand new set of threads for summer, The Keystone Group's outdoor, beachside wine bar is perfect for barefoot, post-swim weekend wines. Pair rose spritzers with Manly Wine's signature prawn and chorizo gumbo, wagyu burgers or a Northern Rivers 150 day grain fed rib on the bone, or perhaps the raw seafood bar is on the cards post-dip — steered by head chef Joel Robinson. They're open for brekkie if you're up that early seizing the day, unless you're more beers and sunsets inclined.

From Saturday, South Steyne Road, Manly.

SUNDAY

Watsons Bay Cider Festival

Summer is nearly upon us. Days are getting longer and the sun is shining near unwaveringly. To celebrate, the good folks at the Watson's Bay Boutique Hotel are throwing a festival dedicated to our favourite crisp fruit beverage — cider. Perched on the Watsons Bay foreshore, this establishment knows a thing or two about hosting chilled summer events, even in spring. Their Cider Festival will span the long weekend October 4-6 and feature a variety of local and imported ciders. Making good use of the fact that cider rhymes with slider, snacks in slider form will be available all day (as will non-rhyming paella). Live music will be plentiful, and for the go-getters among us, there's an apple bobbing competition and a 'cider trail' along Military Road.

Saturday to Monday, Watsons Bay Boutique Hotel.

The Vines Free Carpark Gig

The Vines are a long way from their Rishikesh days. The reformed, Craig Nicholls-run, Sydney staple is back with a new double album Wicked Nature — their sixth studio album — and two new members. Drummer Lachlan West and bassist Tim John have joined Nicholls for the latest reincarnation of The Vines, a band that quite simply refuses to surrender. After a three year hiatus from any touring The Vines will return to the stage for an exclusive one off show to perform their new material — in the carpark of Enmore's Vic on the Park. Creating a bonafide ruckus over the October long weekend, The Vines will play a free show on Sunday, October 5 from 1–6pm.

Sunday, The Vic on the Park, Marrickville.

Ruby's BBQ

Nothing like 16-hour slow smoked brisket and crunchy burgers on a long weekend Sunday. IconPark season two residents, Rupert & Ruby are holding a Ruby’s BBQ event at the Stanley Street location from 11am-3pm on Sunday, with executive Chef, Eli Challenger cooking up specialties for your meat-loving self. Nom on Challenger's Carolina pulled pork and Kentucky fried chicken — which saw Ruby’s BBQ win the coveted People’s Choice Award at Taste of Sydney. Be sure to book for this one, as these melt-in-your-mouth meats are hot property in this town. To make a booking (and you'll need to) visit IconPark.

Sunday, Rupert & Ruby at IconPark, Darlinghurst.

The Glass Menagerie — Belvoir

In the opening monologue of The Glass Menagerie, Tom Wingfield (Luke Mullins), a thinly veiled portrait of Tennessee Williams, informs the audience that he intends to give them "truth in the pleasant disguise of illusion". Soon after, he casually remarks that "The play is memory … it is sentimental, it is not realistic." So which is it to be? Truth or sentiment? Belvoir’s latest production grapples not only with Williams’ text but also his disdain for the theatrical conventions of his time. The Glass Menagerie is not only compelling theatre, it is proof that you needn’t take a hatchet to the classics if you want to make them say something new.

Saturday and Sunday, Belvoir, Surry Hills.

Goodgod Small Club Fourth Birthday

It's hard to believe, but it's four years now that Goodgod Small Club first started bringing its much-needed, eccentric, eclectic good times to the CBD. To celebrate their fourth birthday, they're putting on an epic shindig — as only Goodgod know how. That means, of course, a venue-consuming, all-night-long, convention-obliterating party — this time around themed 'Taking Care of Business'. At the centre of the action will be the Goodgod 'house band' presented by Siberia Records, and Alex Cameron (one-half of Seekae). You can also expect a parade of special guests including Ariane, Astral DJs, Champain Lyf, Drongo, Mike Who, Nacho Pop, Power Suit, Shantan Wantan Ichiban and Tyson Koh. And the dress code? Under the suave 'Taking Care of Business' theme, Goodgod wants to see you looking your public holiday schmickest, so they're asking for suits. Yep, suits. Sharpen up.

Sunday, Goodgod Small Club, Chinatown.

MONDAY

Sydney's Best Coastal Walks

You can walk to the shops. You can walk to work. But no walk will feed your soul like a walk by the water. And if you live in Sydney, your soul should be pizza-party-level full. These ten coastal walks have it all — wild scrub, picturesque paths, yacht clubs and war ruins. Bar stops right where you need them. Parts of the Bondi to Coogee you can blitz in an hour, while the Bundeena to Otford track is an overnighter. Here's your next ten weekends' worth of active leisure.

All weekend, all summer long. Check out our whole test-walked list here.

Foe, Like The Enemy Pop-Up Store

The acquisition of good vintage clothing can be a difficult feat. Much like the metaphoric fog, sometimes you have to sort through a whole bunch of crap until you find something good. Fortunately for us, the guys behind Foe, Like The Enemy have trawled through Asia and the Americas to source the best vintage clothing they could get their hands on. After a wildly successful first pop-up instalment, Foe are holding their second pop-up store in Regent Street, Redfern from September 24 — October 8. For a limited time you can walk into a real-live shop and try on vintage clothes in an actual changeroom — we're talking Jurassic Park denim details, well-worn flannos, as many retro sunglasses as you can predict to lose at a music festival.

Saturday to Monday, Regent Street, Redfern.

Pinot Palooza

Master sommelier Madeline Triffon describes Pinot Noir as 'sex in a glass', while winemaker Randy Ullom calls it 'the ultimate nirvana'. One of the most challenging grapes in the world of vinification, it's also one of the most surprising and rewarding. No wonder Bottle Shop Concepts — the good folk who brought Game of Rhones our way in June — are coming back to town with Pinot Palooza, an epic travelling wine festival celebrating all things Pinot Noir. For just one day, wine connoisseurs in Sydney, Melbourne and Brisbane will have the chance to sample more than 150 drops, direct from the Southern Hemisphere’s best producers. Think Ata Rangi, Yabby Lake, Bay of Fires, Rippon, Kooyong, Mount Difficulty — and that’s just the first few leaves on the vine. Pinot Palooza will hit Sydney on Monday, October 6 at Carriageworks, you can buy tickets right here.

Monday, Carriageworks, Eveleigh.

The Clock Salumeria

Nibble on a piece of Italy this weekend; we're talking meats, cheeses, wines, All the Molto Bene Things. The perfect afternoon or pre-dinner plan, Surry Hills' Clock Hotel is hosting their very own Salumeria, a pop-up bar just for the long weekend. Paying homage to traditional Italian delicatessens (salumeria), mixed boards will feature a range of meats including prosciutto, hot sopressata and capicola alongside cheeses such as gorgonzola, pecorino and taleggio; all complemented by gardiniera, pane de casa and green tomato marmellata. You'll only fork out $20 for two meats one cheese, $30 for four and three, so if you rock up with a small crew it'll cost next to nothing to nibble. And anything involving carafes of Prosecco and Chianti sounds pretty perfect to us. Check out the new Whisky Room while you're at it.

Saturday, Sunday and Monday, The Clock Hotel, Surry Hills.

Gone Girl

The director of Seven, Fight Club and The Girl with the Dragon Tattoo, David Fincher has made a career out of stylish, devilishly entertaining pulp. His latest film, Gone Girl, is absolutely no exception. Adapted from Gillian Flynn's bestselling novel of the same name, it's a dark and twisting tale that presents itself as both a biting commentary on relationships and media frenzy, and a subversion of procedural film conventions. And at the same time, it fully embraces the sleaze and exploitation of that which it critiques. The film is very much double-edged sword. It condemns us for our obsession with violence while funnelling it down our throats. Once again, Fincher is dressing up trash as serious art, wanting to have his cake and eat it too. And frankly, we wouldn't take it any other way.

All weekend, various cinemas around Sydney.

Words by the Concrete Playground team.