And they’re off! Race Season kicks off this weekend, and Sydney will celebrate in her own style. Sydney gets spooky this Friday night for Halloween, and we reveal all the best haunts in town. There’s also never been a better time to hit the coastline for a swim and have a last walk past the Sculptures by the Sea exhibition.
The first weekend of November is always exciting in Sydney. Get your freak on this Friday night for Halloween and hit the best haunts in town for trick or treat with the family (or a grown-ups face painting feast). For a more organised freak-fest, get your scream on at Luna Park with the annual Halloscream attraction. As if the rides weren’t scary enough already, they’ve been elevated to the next level of fear-factor for a weekend of hauntingly good fun.
On Saturday, race season kicks off across the nation, and Sydney celebrates with our very own Golden Eagle Day at Royal Randwick Racecourse. Grab your fascinator and hit the track, or sit back and delight in some delicious dining options brought to you by the Australian Turf Club’s premium food and beverage providers. Here’s my selection of the must-see attractions this weekend in your Sydney playground.
Sydney Staples
1. Sydney Streets on Macleay Street
Sydney Streets is back, transforming some of our favourite neighbourhoods (Pyrmont, Darlinghurst, Redfern, Glebe and Potts Point) into lively hubs celebrating local businesses, community spirit and good times. This week, Sydney Streets will take over iconic Potts Point high street, Macleay Street, featuring a stage at Fitzroy Gardens, roving Halloween-themed entertainment and funky activations. Make sure you drop by local favourite, The Roosevelt, which is known for its Sydney Streets celebrations, DJ sets and cocktails on the street.
Where: Macleay Street, Potts Point, NSW 2011.
When: Saturday, November 1, 11am-8pm.
Price: Free.
2. Halloween Haunts
There’s not one official Trick or Treat Street of Sydney but there are definitely several well-known haunted hangouts that locals descend upon each year like a pack of zombies searching for brains. Head to Chesterfield Parade near the cemetery in Clovelly, or Hastings Parade in North Bondi for the best family friendly old-school door knocking, lolly-grabbing community fun.
My tip is to arrive before 5pm as the treats tend to disappear by 6pm at the latest and be sure to dress to impress. Parents and kids have well and truly embraced the Halloween trend down under and there’s no such thing as too freaky or too fabulous this Friday night.
Where: Chesterfield Parade, Clovelly.
When: Friday, October 31.
Price: Free.
3. Halloscream at Luna Park
Acclaimed as Sydney’s biggest Halloween festival, big kids and little ones can scream to their heart’s content at the famous Luna Park. The iconic amusement park shines after dark with spooky specific rides and events across the weekend for all ages. The big mouth opens at 6pm and includes unlimited rides and entry to the scare maze and “carnival beneath” attraction. My tip, eat your trick or treat candy stash after the rides! And buy your tickets online early, it can sell out.
Where: Luna Park, Milson’s Point.
When: Friday, October 31 to Monday November 2.
Price: $110 general admission.
4. Golden Eagle Day
Giddyup! It’s race season and Melbourne isn’t the only city to get its gallop on. Royal Randwick Racecourse will kick into gear with the $10 million Golden Eagle, Sydney’s second-richest race and the number one event of the Spring season. Think fashion, food and drink, live music, VIP lounge areas and plenty of prizemoney up for grabs. While Melbourne thinks they’re living it up for Derby Day, Sydney Secretly scoops the pool with the best style, sunshine and scrummy dining options. Public gates open at 10:30am on Saturday and in keeping with the Golden Eagle theme, guests are invited to add a “gold accent” to their outfit for the day and no fellas, a gold fake tooth doesn’t count! My advice is to book your dining spot well in advance so you can be sure to get a table and this leaves more time to focus on the field and fabulous fillies on show.
Where: Randwick Racecourse.
When: Saturday November 1.
Price: General admission starts from $39.
Tickets available here
5. LAST CHANCE: Sculpture by the Sea
This is the final weekend for Sculpture by the Sea, Sydney’s iconic outdoor art installation, drawing crowds from across the globe to our Eastern Suburbs natural gallery. The 2km long sculpture walk features around 100 works by artists from across the world, all positioned against one of Sydney’s prettiest pockets for a fusion of art and nature. With giant lizards, dolphins leaping out of toasters, and a stunning Bonsai tree set against the waves of Tamarama, this is one of Sydney’s most popular must-see art events.
Where: Bondi to Tamarama walk.
When: Friday, October 17 to November 3.
Price: Free.
READ MORE: Our favourites at Sculpture by the Sea
6. Sail on Sydney’s first dog-friendly cruise
Dog lovers, rejoice! Sea Sydney Harbour’s new “Dogs on Deck” cruise launches this weekend, letting you set sail with your furry friend. Designed especially for dog lovers, the new one-hour afternoon cruise invites guests to enjoy the stunning sights of Sydney Harbour with their four-legged companions by their side. If your dog loves sticking their head out of the car window, imagine the upgrade on a sleek catamaran, sea breeze ruffling their fur. The sailing will take place aboard a spacious 10.5 metre catamaran, which can cater for a maximum of 20 dogs.
You can book your spot on the upcoming cruise here.
Where: Pickup at Man O War Steps, Circular Quay (next to the Sydney Opera House).
When: First sailing on November 2.
Price: Tickets cost $69 per adult, $19 per dog and $29 for children ages 3-12.
READ MORE: Sydney’s first dog-friendly cruise encourages guests to set sail with their pups
Where to Eat and Sip
7. Otto’s 25 years 25% off
One of Sydney’s most celebrated restaurants is 25 years old, and to celebrate, they’re smashing 25% off your bill. Now that’s a mouth-watering reason to celebrate! Set against Sydney’s sexy Woolloomooloo backdrop (try saying that after a celebratory bottle of champagne), Otto Ristorante oozes class. Any restaurant that spells its name as Ristorante automatically makes it flash btw. This Friday night is the final night to snap up some snapper and snag a bargain with a classy meal under the stars, watching the “haves and the have yachts” saunter up and down the finger wharf in their boat shoes. Tip, to redeem the discount, mention “Happy Birthday” when booking or upon your arrival. Love a secret code!
Where: Otto Ristorante, Finger Wharf, Woolloomooloo.
When: Ends Friday October 31.
Price: 25% off final bill.
8. Celebrate World Champagne Day with Solotel
The bubbles just keep on popping at Solotel following World Champagne Day. This fizzy and fabulous collaboration between Solotel and Veuve Cliquot, plus Brolos Western Rock Lobster, has launched Cliquot and Claws, a limited-time indulgence to showcase the iconic pairing. The kick-off weekend was so successful, the fun will continue up until Sunday, with an exclusive menu across five venues, including Aria, Barangaroo House, Chiswick, Chophouse Terrace and North Bondi Fish.
The menu includes a smashed Brolos lobster burger ($25) and Brolos grilled half lobster with herb & garlic butter, and frites ($45), which you can pair with a glass of Veuve for $15. Visitors to these venues can also opt for a bottle of Veuve for $99. My tip: bring your best lobster bib and prepare to get your hands dirty!
Where: Select Solotel venues: Aria, Barangaroo House, Chiswick, Chophouse Terrace and North Bondi Fish.
When: Saturday November 1 and Sunday, November 2.
Price: Varies depending on order.
9. Messinaville Gelato
When you start adding the word “ville” to the end of your name, you know you’ve officially made it. Messinaville is on the map, folks! After the humble origins in Darlinghurst in 2002, this gelato hole-in-the-wall has become an iconic institution and one that Sydney is proud to boast as their own! The new Marrickville HQ features their flagship gelato store, a chocolate counter, their offices and the full production factory, where everything that is served up in their various stores is made. Get your sweet skates on and head down for a day dripping in coffees, pastries, pancakes, and of course, gelato.
Where: Messinaville, 1 Rich Street, Marrickville.
When: Saturday and Sunday, 8am until late. .
Price: Free to join the fun.
10. Sydney’s best long lunch
Named by Time Out Magazine as Sydney’s best Sunday brunch or long lunch, Sean’s Panorama in Bondi is hard to beat. It’s not your flashy, show pony vibe you’d imagine, but rather an intimate, quaint, welcoming little spot with immaculate attention to detail and a menu that will make you feel all sorts of emotions. Chef and owner Sean Moran has been dishing up these gourmet delights for years, with mostly locals being in on the secret, but word has spread, and despite the now busy booking list, you’ll still be made to feel like you’re a VIP guest when you dine here. My strong advice is to select the Sunday roast chook for a poultry mouth-explosion like no other. It’s also the perfect place to stop after you’ve finished the Sculpture by the Sea exhibition at the south end of the beach.
Where: Sean’s Panorama, 270 Campbell Parade, North Bondi.
When: Open every Saturday and Sunday.
Price: $140 for a three-course meal, plus drinks.
Markets and Shopping
11. Second Life Markets
Second Life Markets return to Sydney this weekend, with over 120 stalls taking over Carriageworks on Sunday. As second-hand shopping continues to be a trend that everyone can get behind, these markets are not to be missed, arriving at the perfect time to upgrade your summer wardrobe. There will also be local DJs, a lineup of food trucks, drinks, and plenty of curated vintage finds.
Where: Carriageworks, 245 Wilson St, Eveleigh NSW 2015.
When: Sunday, November 2.
Price: From $5.
READ MORE: Second Life Markets’ Nadia Razlan talks Sydney fashion, vintage clothing and top thrifting tips
12. Tramshed Markets
You probably haven’t heard of the Tramshed Markets (simply “Tramsheds” for cool folks), but you should be. It’s about as eclectic a market as can be, making it the perfect place to hang out at any time of the weekend. From the breakfast buffets and bakeries to the sunset bars and restaurants, these permanent markets are also an artisan’s delight to show off their best wares and tempt you with their tastiest titbits.
Where: Tramsheds, 1 Dalgal Way, Forest Lodge.
When: Saturdays and Sundays, 9am–3pm.
Price: Free entry.
13. Carriageworks Farmer’s Market
A favourite for locals and tourists alike, Carriageworks Farmers Markets brings an array of fresh produce from all over the country to the precinct in Eveleigh. Whether you’re after homemade butter, granola and yogurt bowls, fresh flowers or organic wines, there’s something for everyone. Grab a loaf of bread from A.P. Bakery’s stall, or pick out some super-fresh veggies from one of the many stalls. After your shopping spree, chill out and perch on one of the many seats, which provide the perfect opportunity for people watching.
Where: 245 Wilson St, Eveleigh.
When: Open Every Saturday, 8am-1pm.
Price: Free entry.
Concerts and Gigs
14. Feverup Candlelight Tribute to Taylor Swift
Let this concert ignite your inner glow with a sensory tribute to the one and only Tay Tay. St Stephen’s Uniting Church in the city sparkles with candles and talented musicians who dedicate the evening to your favourite songstress’s best hits. There’s nothing quite like live music in an intimate setting, surrounded by the warm glow of candles and being serenaded by an orchestra. Grab a friend, a family member or even your teenagers and enjoy a night out where you don’t even have to be a Tay Tay fan to be swept away. And the best part? It’s only a fraction of the price you’d pay for an actual Taylor Swift concert ticket!
Where: St Stephen’s Uniting Church, 197 Macquarie Street, Sydney.
When: Saturday, November 1.
Price: Starting from $57.50.
15. TWICE at Qudos Bank Arena
K-Pop band TWICE have embarked on their latest world tour <THIS IS FOR> and is en route for their Aussie leg on November 1 and 2. Qudos Bank Arena will go K-pop crazy this weekend when the megastars descend for an evening of 360-degree stage performances at getting up close and personal with the fans. Known for their catchy songs and synchronised dance moves, this nine-member group has grown into one of the most influential and famous K-pop artists in the world. With over 20 million cumulative album sales across Korea and Japan, TWICE continues to break records, becoming the first female K-pop group to headline North American stadiums.
Where: Qudos Bank Arena, 19 Edwin Flack Ave, Sydney Olympic Park.
When: Saturday, October 25, at 7pm.
Price: Tickets start at $109.90.
What’s on in Theatre
16. Phar Lap: The Electro-Swing Musical
The Sydney Fringe Festival may be over; however, wacky and wonderful theatre is here to stay. Enter Phar Lap: The Electro-Swing Musical. Written by award-winning music director and composer Steven Kramer, this comedy explores the life of Phar Lap, Australia’s most famous racehorse, in what Kramer calls “the true underdog story”.
Kramer is on a mission to prove that Australia doesn’t need to rely on theatre imports — he wrote Phar Lap: The Musical as proof that Aussie theatre can stand proudly on its own. Independent venue Hayes Theatre in Potts Point hosted the debut of the new musical comedy last week, with Joel Granger taking on the role of Phar Lap. Audiences may recognise Granger from Australian productions of The Book of Mormon, Hairspray and West Side Story. He also recently starred as Benny Southstreet alongside Cody Simpson in Guys and Dolls with Opera Australia, proving that while the venue may be intimate, the talent is top-tier.
Where: Hayes Theatre, 19 Greenknowe Ave, Potts Point.
When: October 17-November 22.
Price: From $60 per person.
17. Calamity Jane at the Sydney Opera House
Grab your gun holsters gals, Calamity Jane is in town and she ain’t messin’ around! The classical musical has been stripped bare again and reimagined with Virginia Gay at the helm. Deadwood is the place, Jane is the sharpshooter, and the American West is where the calamity ensues. Back by popular demand, Gay returns to her role as the magnetic, masculine heroine exclusively for the Sydney Opera House season of this award-winning production. My top tip is to buy tickets for the 1pm daytime show, instead of the 7pm show, where you’re likely to snap up the best seats.
Where: Joan Sutherland Theatre, Sydney Opera House, Bennelong Point, Sydney.
When: Saturday, September 27- November 1.
Price: Tickets start at $49.
18. Back to the Future: The Musical
When it opened in London, Back to the Future: The Musical quickly became a success story, scooping up the Best New Musical award at the Laurence Olivier and What’s On Stage awards. It also swiftly transferred to Broadway. Now, the musical is dazzling Sydneysiders at the Lyric Theatre, with breathtaking visuals and a real flying DeLorean.
The exciting cast lineup includes Tony Award-winning actor Roger Bart, who will reprise the role of Doc Brown, having impressed audiences in both the West End and Broadway. Starring opposite him as Marty McFly will be Axel Duffy, a rising star from Brisbane. You can read our review of the new production here.
When: Friday, September 26, until Sunday, December 28, 2025.
Where: Sydney Lyric Theatre, 55 Pirrama Rd, Pyrmont NSW 2009
Price: From $89.
19. The Book of Mormon
Regarded by many as one of the funniest (and most outrageous) musicals of all time, The Book of Mormon was written by the masterminds behind South Park, Trey Parker and Matt Stone. The musical tells the story of two young missionaries from the Church of Jesus Christ of Latter-day Saints: “perfect” Elder Kevin Price and socially-awkward Elder Arnold Cunningham.
Kevin hopes his mission will take him to sunny Orlando, Florida, but instead, the mismatched pair are sent to a remote village in Uganda. The result is chaos, comedy and a lot of outrageous satire. We won’t spoil the show, but if you want to find out more, read our review here.
When: Now showing until Sunday, November 30, 2025. Shows take place on most Tuesdays–Thursdays 7pm, Fridays 7:30pm, Saturdays 2pm & 7:30pm and Sundays 1pm & 6:30pm.
Where: Capitol Theatre, 13 Campbell Street, Haymarket NSW 2000.
Tickets: From $69 per person.
READ MORE: The Book of Mormon is back in Sydney — here’s everything you need to know
Art Exhibitions and Galleries
20. Ricky Swallow, Bent Forms
Who would’ve thought that what was missing from your shot of the Opera House was a giant bent stainless steel spoon? Ricky Swallow’s commission for the MCA’s Loti Smorgon Sculpture Terrace sees four huge spoons dotted across the lookout. They were created by Swallow from scaled-up wax prints of actual teaspoons, which he bent into various shapes. Head to the terrace and enjoy panoramic views of Sydney’s iconic harbour as you check out the wacky pieces of art by Swallow. If you loved Sculpture by the Sea, this exhibition is also worth a visit.
Where: Loti Smorgon Sculpture Terrace, MCA, 140 George St, The Rocks NSW 2000.
When: Showing until July 20, 2026.
Price: Admission from $20.
21. Dangerously Modern: Australian Women Artists in Europe 1890-1940
This brand-new exhibition at the Art Gallery of NSW celebrates the remarkable women artists who overcame social barriers to forge international careers beyond Australia. This exciting exhibition is the first to celebrate the vital role of Australian women in shaping international modernism, featuring iconic figures like Margaret Preston, Nora Heysen and Grace Cossington Smith, as well as the under-recognised Agnes Goodsir, Justine Kong Sing and Helen Stewart. The exhibition will show more than 200 works, expanding visitors’ understanding of modern art movements, including realism, impressionism, post-impressionism, cubism and abstraction.
Where: Art Gallery of NSW, Art Gallery Rd, Sydney NSW 2000.
When: October 11- February 15, 2026.
Price: Adult tickets: $35, Youth: $18.
22. Mike Hewson: The Key’s Under the Mat
New Zealand-born, Sydney-based artist Mike Hewson is next in a long line of artists aching to take over The Art Gallery of NSW’s unique, subterranean Nelson Packer Tank space, turning the industrial bunker into a concrete jungle with a park, play space, construction site, and a communal area framed by sculptural works.
Mike Hewson: The Key’s Under The Mat opened last Saturday, and is the current talk of the art world. It marks the artist’s first solo presentation in an art museum, a platform to heighten his unique approach to what an all-ages playground looks like. Visitors are encouraged to meet, dwell, play, make, perform and explore while interacting with the park’s various features. You can even do a load of laundry or take a shower in the space!
Where: Art Gallery of NSW, Sydney.
When: From October 4, 2025.
Price: Free.
