The Coolest Things to Do in Sydney This October



From prosecco-laced long lunches and immersive cocktail tours to late-night gigs and artistic fairs – Sydney has plenty to keep you occupied this month. Make sure you don’t miss a thing with our top picks of things to do throughout the rest of October.


Chiswick Woollahra and Chandon are welcoming the warmer spring evenings with the launch of Rosé on the Lawn. The sprawling and luscious Chiswick lawn will come alive with live acoustic tunes, garden games and roaming canapés, all completely free of charge. Guests can purchase flowing glasses of Chandon sparkling rosé, as well as an array of speciality Chandon rosé cocktails. Try your hand at a game of bocce or lawn bowls or take a seat on the lawn with a glass or two of rosé.

Thursdays in October, 5:30pm-7:30pm


65 Ocean Street, Woollahra

Local favourite Park House is dishing up sophisticated eats from its formal dining space, The Restaurant. Big on flavour and direct from the fire, the food is refined yet homely. From wood-baked whole fish and minute steak frites, to rotisserie chicken and indulgent fudge brownie, there is something for everyone to enjoy. First date, family dinner or a mid-week catch up, The Restaurant offers friendly table service and an extensive wine list ranging from local drops to European wines, that will help celebrate any occasion.

2 Park Street, Mona Vale

Spring is definitely in the air, so what better way to celebrate than with a Bottomless Rosé lunch? Every Saturday in October, Hartsyard will be pouring bottomless Sangiovese Rosé from Sparrow and Vine for just $35pp, from 12pm to 2:30pm. Guests can enjoy their rosé alongside delicious dishes designed to share including fried cheese with hot mustard, grilled baby cuttlefish skewers, kangaroo tartare and kingfish sashimi.

Every Saturday in October, 12pm – 2:30pm

$35pp (For bottomless rosé and full menu available for purchase)

33 Enmore Road, Enmore

Beam Suntory has announced the launch of Sip and Stroll – a guided cocktail tour through some of Sydney’s hidden nightlife gems. From trending cocktail bars to the most impressive new establishments, the Sip and Stroll tours will reveal a suite of the most tantalising cocktails crafted by Australia’s finest bartenders.

Throughout the month of October, two intimate Sip and Stroll cocktail tours will be held weekly on Thursday evenings and Saturday afternoons. Perfect for those who are new to Sydney nightlife or veterans looking to re-visit some of Sydney’s best haunts, the tour guide  ̶   world class cocktail expert Cam Pirret  ̶  will take you through an immersive experience leaving no cocktail untouched, from a Maker’s Mark Old Fashioned to a classic Sipsmith Martini.

Thursday: 3rd October, 10th October, 24th October, 6:30pm-9:30pm

Saturday: 5th October, 12th October, 19th October, 26th October, 3:30pm-6:30pm

$60pp (+BF)

Meeting Point: The Rook, Level 7/56-58 York St, Sydney

Day drinking has never looked so good with Jamie’s Italian offering a $50 long lunch with bottomless prosecco on weekends throughout October. Dine on pasta, polenta chips, and bottomless prosecco for two hours. For those who want something sweet, they are giving guests the option to add an espresso martini or any dessert for just $10.

Weekends in October, 12pm-4pm


107 Pitt Street, Sydney

Every Thursday is taco day at Harry’s but this Thursday it’s an extra special one to celebrate International Taco Day. On 3rd October, gear up for a one-day Mexican fiesta with a huge $5 taco menu, with options for everyone, not to mention a selection of Mexican inspired plates. At the bar you’ll also be able to grab $5 Mexican beers and $10 margaritas all day long.

Thursday 3rd October, 11am-10pm

Free entry (Menu from $5)

40-44 Wentworth Avenue, Surry Hills

Nola Smokehouse & Bar (Credit: Steven Woodburn)

All You Can Eat Meat, NOLA Smokehouse & Bar

Every Sunday, you can indulge in unlimited, succulent smoked meats for just $65 per person at NOLA Smokehouse and Bar. You’ll receive endless amounts of all their smoked meats including Rangers Valley black onyx brisket, slow-roasted and hot-smoked pork shoulder, blackened organic chicken with Creole spices, free range Milly Hill cold-smoked lamb and NOLA’s Andouille Cajun-spiced sausage. Plus, you can order one side per person choosing from the likes of fries with sweet and spicy BBQ salt, Southern slaw or fried Brussels sprouts with blue cheese mayo and hot sauce. Now, that’s our kind of feast.

Sundays in October (Lunch only)


Level 1, Tower 1, 100 Barangaroo Avenue, Barangaroo

Each Sunday in October, Hotel Rose Bay are holding an intimate long lunch that takes diners through the journey of fresh produce from soil, vine, sea and vat to Hotel Rose Bay.

On the 6th and 20th, the lunch will be hosted by James Squire, with a Beers + Bites seven course lunch with matching beers for every course ($90pp). On the 13th and 27th, Margan Estate will host a Wine + Dine five course degustation lunch with matching wines ($120pp).

Sundays in October

From $90pp

807 New South Head Road, Rose Bay

Saké Restaurant & Bar is celebrating a decade of delivering its signature, super-fusion Japanese food at its up-market location in The Rocks, Sydney where the remarkable Saké journey began in October 2009. In honour of its 10th birthday, Saké The Rocks will showcase the delightful, modern riff it brings to Japanese cuisine at an exclusive, seven-course dinner, paired with Champagne, wine and Japanese drinks.

Wednesday 16th October, 6:30pm


12 Argyle Street, The Rocks

Chargrill Charlie’s is cheering on the Wallabies in the2019 Rugby World Cupby offering free chicken family packs every time Australia wins. Aussie fans simply need to visit one of the thirteen Chargrill Charlie’s stores in Sydney wearing their green and gold Wallaby jersey, cap, beanie or scarf to enjoy the Wallabies family pack offer, featuring a whole stuffed chicken, large salad and large chips or wedges. The deal is available for 24 hours after the final whistle is blown and also includes an Aussie-themed Chargrill Charlie’s trucker cap with every pack.

Annandale, Mona Vale, Wahroonga, Mosman, Willoughby, Drummoyne, Neutral Bay, Woollahra, Frenchs Forest,  Rose Bay,  St. Ives, and Lane Cove  

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