Everything you need to know about what's happening this month in Sydney

Ahh…yet another wonderful month in Sydney town. The sun is shining, summer is nigh, and it appears that everyone has collectively decided to have friends again.

My favourite time of year!

This month, it’s safe to say that the city is ramping up big time. You thought you were busy in October? I have news for you, doll. It’s live gig galore, and you’ll be so busy scoffing down bottomless bao buns and Aperol spritz that we’ll be surprised if you come up for breath.

Yes, you’re in for an absolute treat this month. Lucky you. So what are you waiting for? Whip out those Google calendars and get planning, because here are the best things to do in Sydney this month.

Sydney Cellar Door

Image: @chiswickwoollahra

Wine lovers rise up, I have good news. This month is officially NSW Wine Month, meaning the entire town is being taken over by some of the state’s best local wineries. From long lunches at Blue Door, to winemaker dinners at Kin, you’re absolutely spoiled for choice when it comes to events this month.

And with all that being said, our monthly pick has to go to the Sydney Cellar Door event. Happening across the second weekend of November, over 40 NSW wineries are banding together in Circular Quay to deliver what might possibly be the ultimate wine crawl. The two-day festival will see our local winemakers showcase some of their best farm to glass tipples, proving once again that you don’t need to travel far for a good sip.

WHEN: Saturday 9 and Sunday 10 November
WHERE: First Fleet Park and Tallawoladah Lawn
HOW MUCH: Free entry
CHECK IT OUT HERE.

Sydney Streets Series

Image: City of Sydney

Yes, that’s right, the famous Sydney Streets series is back again this month and proving to Sydneysiders that we can, in fact, do the whole European alfresco thing. This month will see Harris Street and Redfern Street closed off for the ultimate day-to-night festivities. And if the most recent Stanley Street party was anything to go by, these ones can heave. Our bets are on Redfern Street kicking off come Saturday 16 November. Day drinking on the streets with your mates – what could possibly go wrong?

WHEN: Saturday 9 and 16 November
WHERE: Harris Street and Redfern Street (respectively)
HOW MUCH: Free entry
CHECK IT OUT HERE.

Pier Dining All You Can Spritz

Image: Supplied

I don’t make the rules. Springtime calls for bottomless Aperol fuelled brunches with the girls. And I know I’m not the only one who will go actually feral for a sunny day and an outdoor dining space. So thank god PIER Dining at Pier One Sydney Harbour is playing make-a-wish, because they’re slinging an epic Friday and Saturday all-inclusive special that shouldn’t be missed.

For $89, they’re treating guests to a 1.5-hour experience filled with Freemantle octopus, crisp potato scallops, pistachio and asparagus malfadine and pavlova. Of course, we can’t forget the spritz cocktails they have on offer – from your classic Aperol to a Dockside sparkling with Davidson plum. In other words, you’ll know where to find us.

WHEN: Every Friday and Saturday at 12.30pm
WHERE: PIER Dining, Pier One Sydney
HOW MUCH: $89
CHECK IT OUT HERE.

Peggy Gou at Munro Warehouse

Image: Vogue UK

I can’t explain, I got a feeling that I just, I can’t erase. Okay, I’ll stop, sorry. But hopefully by now you’ve pieced together that the electronic queen herself, Peggy Gou, will be playing live at Munro Warehouse this month. Anyone who’s ever had a hot girl Euro summer has probably already caught a set, but it’s a far rarer occurrence for the DJ to be making her way down under. Perfect way to ring in summer, I say. Tickets are also surprisingly still available, but I’ll place bets that they’ll be gone asap.

WHEN: Saturday 16 November, from 7pm
WHERE: Munro Warehouse
HOW MUCH: Tickets are $120
CHECK IT OUT HERE.

Patrick Topping at Ivy Saturday

Image: Patrick Topping

More! Live! Music! We honestly all have to stop whinging, because this month is actually going off when it comes to gigs. Renowned house artist, Patrick Topping, is also making his way over to Sydney shores this month for a one-off gig at Ivy. Some people won’t recognise the name, but I promise you’ll know the tunes (that is, if you have decent music taste). Be Sharp Say Nowt, Voicemail and Forget are just a few of his marvellous creations. Tickets are still left, but like before, these will GO.

WHEN: Saturday 30 November, from 9pm
WHERE: ivy
HOW MUCH: From $63
CHECK IT OUT HERE.

Red Bull Cliff Diving World Series Final

Image: Red Bull

Ok, a momentary break from live gigs is probably necessary. Which is why I bring to you the Red Bull Cliff Diving World Series Final. Random, I know, but it brought a massive turnout last time in 2022, and we expect no different this year. In short, 12 men and women each launch themselves from platforms over 20m high, and are ultimately judged on their diving skills. Sydney’s hosting the final again, meaning two people will be crowned champion. It’s happening over three days, but Sunday is when things start to really get good. Honestly worth the check out.

WHEN: Friday 8 to Sunday 10 November, from 11am
WHERE: Fleet Steps, Mrs Macquarie’s Chair
HOW MUCH: Free
CHECK IT OUT HERE.

Garage Sale Trail

Image: Timeout

Looking for some retail therapy this month? Or perhaps you’re trying to coordinate a good ol’ fashioned spring clean before December arrives? We’ve got you covered. Introducing Garage Sale Trail, Australia’s largest secondhand treasure hunt happening across two weekends this month.

In essence, the organisation allows homes and businesses to set up shop and list their very own garage sale online. In other words, you won’t have to coincidentally stumble upon one on your weekend stroll. Instead, make a map and get shopping across town. And if you’re interested in hosting your own, it’s free to register. Ahh..technology truly is a wonderful thing.

WHEN: Saturday 9 and Sunday 10, Saturday 16 and Sunday 17 November
WHERE: Across the country (see online listings)
HOW MUCH: Free to register store, free to attend
CHECK IT OUT HERE.

Head On Photo Festival

Image: Sydney.com

Australia’s leading photography festival is back again this month, meaning you can get your fix of culture in. Bondi beach, Bondi Pavilion and the Paddington Reservoir Gardens will all be taken over with a plethora of emerging and established Australian and international artists. Highlights include the Festival Launch Party happening on Friday 8 November, VILLAGE Hearing the Grass Grow by Michael Coyne and Bridging the gap – First Nations photographers presented by Barbara McGrady, Tace Stevens and Milly Hooper. Added bonus, it’s all free to the public.

WHEN: Until Sunday 1 December
WHERE: Various locations
HOW MUCH: Free
CHECK IT OUT HERE.

McGuffin Park at Ensemble Theatre

Image: Via Aussie Theatre

If you fancy a little dinner-and-a-show moment this month, check out the world premiere of McGuffin Park at Kirribilli’s Ensemble Theatre. Set in the small Aussie town of McGuffin, the play follows the chaos that unfolds when the mayor unexpectedly resigns just one week before mid-term elections. Expect anti-government agendas, meddling journalists, blackmail, and friendships pushed to the edge. It’s funny, thought-provoking, and definitely worth a watch.

WHEN: Until Saturday 23 November
WHERE: Ensemble Theatre, Kirribilli
HOW MUCH: From $43
CHECK IT OUT HERE.

Edinburgh Gin x ACID.FLWRS Pop Up

Image: Supplied

Attention all gin and/or art lovers. Edinburgh Gin is partnering up with iconic floral artist ACID.FLWRS to deliver one of the coolest pop ups in town this month. On Friday 8 and Saturday 9 November, the brands are taking over Rainbow Studios in Darlinghurst to deliver the ultimate immersive art and cocktail experience. You’ll be able to catch some of Claire Mueller’s vibrant floral sculptures forming part of her installation Filled With Wonder. Of course, no artsy evening would be complete without an array of some signature gin cocktails all thanks to Edinburgh Gin.

WHEN: Friday 8 and Saturday 9 November
WHERE: Rainbow Studios, Darlinghurst
HOW MUCH: Free
CHECK IT OUT HERE.

Summer Dance

Image: Instagram @kilkakreative

Ladies and gentlemen, I have fabulous news. Sydney’s favourite day-to-night party is officially back for a sun-drenched takeover this month. This is the type of party that gives major Brooklyn vibes, and promises impeccable music. Yes, Summer Dance is back and hosting a string of sets that’ll make you question whether Sydney’s music scene ever really died.

Grab a Day Party ticket and expect the likes of TSHA, DJ HABIBEATS and Rakish + Jhassic on the decks. This one’s hosted outside at the Liberty Hall Courts, which gives major summer party vibes. Alternatively, opt for an After Dark ticket to see DJ EZ, Mincy and Garage Pressure inside Liberty Hall. Really, there’s no wrong choice (or you can do both, lol).

WHEN: Saturday 9 November, from 3pm
WHERE: Liberty Hall
HOW MUCH: From $59
CHECK IT OUT HERE.

Free Foot Massages at Birkenstock Pop Up

Image: Nordstrom

Birkenstock is turning 250 years old. You heard that correctly. The brand is literally older than the federation of this country, so it’s understandable they’re looking to celebrate. On Friday 8 and Saturday 9 November, the iconic sandal will be taking over Chinatown Country Club for a free-to-the-public event. There’ll be free foot massages, as well as the Walk This Way travelling exhibition. Definitely a fun work break activity.

WHEN: Friday 8 and Saturday 9 November, from 10am
WHERE: The Apartment, Chinatown Country Club
HOW MUCH: Free
CHECK IT OUT HERE.

Mexican-Asian Bottomless Brunch at Woollahra Hotel

Image: Supplied

Oh the yuppies are going to love this one. This month, the Woollahra Hotel is opening it’s doors to the Festival of Tequila, so you know they mean business. And while the Hotel will be running an array of specials throughout the month, our pick has to be their Bottomless Weekend Brunch series. Every Saturday and Sunday in November, they’ll be slinging the likes of Caliente wings, Trevally ceviche and prawn wontons up to your eyeballs. Of course, the Mexican-Asian feast wouldn’t be complete without bottomless mimosas, bellinis, wines and beers. On Sunday 3 and 10 November, you’ll even score a live Mariachi band.

WHEN: Saturdays and Sundays in November, 12pm to 4pm
WHERE: Woollahra Hotel
HOW MUCH: $89 ($20 additional for frozen Don Julio margarita slushies)
CHECK IT OUT HERE.

Pearl Jam Alive 1991-1992 Exhibition

Image: Behind The Gallery

In celebration of rock band Pearl Jam’s return to Australia in over 10 years, Paddington is playing host to a seriously cool photography exhibition. Presented by Chris Cuffaro, the LA-based photographer is taking us back to the band’s prime days during their early careers. Expect never-before-seen, behind-closed-doors imagery that will send you straight back to the early 90s. To top it off, he’ll also be hosting talks and live performances throughout the week.