What's On This Weekend in Sydney: Our Sydney Editor's Top 5 Picks

Spring is in full swing, and our stunning harbour city is buzzing with exciting things to do - perfect for whatever mood you're in.

With the weather gearing up to be a spot cloudy, we're planning on a long lunch and some market shopping. We're also excited for the inagural pup cup, an alternative to the Melbourne Cup. Find it all below with our top five picks of what to do in Sydney this weekend. 

Sydney Cellar Door 

Fancy tasting 16 of NSW's wine regions without having to step foot out of Sydney? It's your lucky day! This November, The Rocks will be playing host to the tasting event of all tasting events. There will be 40 wineries in attendance with festival packs available for purchase. $30 will score you 5 tokens and a reusable tumbler so you sip your way around sustainably. The perfect spring weekend out! 

Saturday 9th November to Sunday 10th November 

Tallawoladah Lawn, The Rocks

Take a Dip at Sydney Harbour's Newest Swimming Spot

The good people at Pier One Sydney Harbour sure know how to have a good time. They've just transformed their private pontoon into a free swimming spot for anyone and everyone. Giving beach club vibes with a side of incredible views, you can book for groups of 10+ or just turn up. Entry is free and guests can order food and drinks straight from the bar! 

Free 

Friday 1st November to Friday 31st January, 11am to 6pm 

Pier One Sydney Harbour 

The Puppy Cup

As far as good causes go, you won't find one better than this. Puppy Cup is taking place this weekend and we're urging all dog-lovers to make their way over to Intercontinental Double Bay.

The event, hosted by Mon Petit Amour Manolo and Pound Paws Charity, will be raising funds to support the rehoming and rescue of pets. There will be rescue pup races (with vets placed on which dogs will be adopted first), a showcase if kyxury pet jewellery from Mon Petit Amour Monolo, a pledge station, fundraising raffle, live paw-traits and champagne, gourmet canapes and harp music. 

Saturday 9th November, 5pm to 7pm 

Courtyard, Intercontinental Hotel Double Bay

Catch a Flick at the Laneway Cinema 

Save some cash this summer with the return of Laneway Cinema in The Rocks. Settle in on bean bags and deck chairs for a movie under the stars. The cinema will be open every Wednesday from 7pm with free tickets available online and walk-ins welcome. You can also make a donation for popcorn with all proceeds going to a different charity each month, 

Free

Wednesday 6th November to Wednesday 26th March 2025 

The Rocks

Settle in for Sunday Lunch at Cafe Sydney 

Cafe Sydney has long been a favourite for a lazy Sunday lunch and they've just made it all even easier with a new three-course a la carte Sunday menu. Each Sunday they'll also have a selection of magnums and vintages ready and waiting to be poured by the glass as well as a spotlight on a different local distillery each month. 

$145 per person 

5th Floor, Customs House, Circular Quay 

Haven't found your perfect weekend plans yet? Check out the best new restaurants openings in Sydney or our monthly guide to read about everything else that's happening this month in Sydney.