Your Sydney Optimum October

Rebecca Varidel
1st Oct 2023

Sydney get ready for fun + mischief this October. Here's our independent curated guide to what's on...

Highly celebrated, ARIA-nominated and award-wining artist, Emma Donovan performs across genres including gospel and soul. Emma will be performing on our 50th birthday 28 October in the Sydney Opera House Concert Hall for her headline debut and will be exclusively releasing one of the new singles at the concert from her upcoming country soul album. This is a new direction from Emma in terms of her music, departing from exclusively soul and R&B to explore the country genre, and we’re delighted that she will be premiering it as part of the Sydney Opera House 50th birthday celebrations!

Message In A Bottle is a powerful, poignant and beautiful work about the global refugee crisis and the strength of human resilience. A co-production with Sadler’s Wells Theatre and Universal Music UK, it will premiere in the Joan Sutherland Theatre, Sydney Opera House between 25 - 29 October.

Inspired by the hits of music icon Sting, Message In A Bottle is a high-energy, visually and emotionally evocative dance narrative that follows the lives of three siblings after their village is torn apart by war. Its creator, the five-time Olivier Award nominee Kate Prince of Zoonation, was compelled to create this production after witnessing the impact of the refugee crisis on families. Renowned musical arranger Alex Lacamoire (Hamilton, The Greatest Showman, In The Heights) was the musical supervisor and arranger for this dance work too and was instrumental in reimaging Sting’s music for this production including working with the iconic musician on some new arrangements for Message In A Bottle.

The Hunchback of Notre Dame based on the Victor Hugo novel and songs from the Disney film, is performing at Rockdale Town Hall until 8 October and our very own Declan Dowling is performing in it. Be there or be square. The Regals Musical Society is a community based, not-for-profit organisation in Sydney producing quality musical theatre productions, based in Rockdale NSW, with the objective of engaging their audiences and nurturing the talent of their members.

Oxford Cabaret Festival sashays into the limelight at the brand-new Meraki Arts Bar, nestled in the heart of Darlinghurst on iconic Oxford Street from 23 October. This exhilarating celebration of creativity promises to be an unmissable extravaganza, featuring a tantalizing mix of seasoned legends and emerging talents. It's just $25 for a single cabaret performance or $35 for a thrilling double bill on the same evening.

Sydney Spring Mischief 2023 continues with all the fun of the queer circus cabaret show, Cirque X 3 - 8 of October, In The Vault down at The Entertainment Quarter at 6.830pm each night.

BIG DANCE 2.0 - A CELEBRATION OF GROUNDBREAKING DANCE is our call for the Sydney must see of the month - October! Picture this – 9 dancers, singing, a boxing ring, a live-stream, and a snake. Intrigued? You should be! Don’t miss the latest work by Australia’s only collective-led dance company, Dance Makers Collective (DMC), at BIG DANCE 2.0, Riverside Theatres, Parramatta, 12 - 14 October.

BIG DANCE 2.0 features contemporary works by dancers and choreographers from across NSW, including Australian Dance Award winner Jana Castillo, this year’s Sydney Dance Company New Breed choreographer Eliza Cooper and emerging First Nations dance artists Jye Uren and Amy Flannery, to name a few.

Halloween Return to Rio is well and truly BACK for an otherworldly affair. It’s time to dust off the cobwebs, put on your dancing shoes, and prepare for a spinetingling weekender like no other this 27 - 29 October at Del Rio Riverside Resort, Wisemans Ferry. To celebrate its resurrection, the Rio team has assembled a spellbinding world of wonder, alongside a concoction of the most cutting-edge names in dance and electronic music from far and wide. With the likes of Patrice Bäumel, Sneaky Sound System, Late Nite Tuff Guy, Nick Warren and Mark Farina topping the musical bill, devilish drag icons, a freak circus and Frankenstein and his bride are just some of the more eclectic entertainment that awaits at Australia’s most spooktacular fancy dress party.

Headlining the Halloween antics is Pickle’s Family Funerals, who will be hosting an immersive theatrical experience where Rio revellers will be able to take part in their very own funeral. So, pull up a pew and say a prayer or two. With a pool party to die for, the weekend’s colourful shenanigans will see the Day of the Dead take hold of the Del Rio piscina. The margaritas will be flowing, and the tunes will be pumping. On the spiritual side, our Voodoo Fortune Teller will be delivering premonitions about your future, while an experienced shamanic practitioner, alchemist, and pranic healer will be hosting Himalayan breathwork and cacao ceremonies. Promising to activate a sense of clarity and bliss, these sessions will reignite the nervous system to keep the vibes high for the entire weekend.

Parramatta Lanes is back and bigger than ever, bubbling to life from 11 - 14 October, and serving a stellar line up of musicians. This year features 120 acts over seven stages. From hip hop to house, ballroom to Bollywood, Parramatta Lanes is turning on a diverse mix of sounds and performances. Highlights include Honeytrap Sound System, Sydney’s first femme-led sound system collective who will deliver a vibrant performance inspired by their roots in Reggae, Cuban & Caribbean music.

Hip-hop artist and South-West Sydney local L-FRESH The LION will be bringing Campbelltown Arts Centre’s ‘Conscious’ collective to the stage with a curated program of local hip hop artists set to represent the scene. Was a rapping robot that can drum on your 2023 bingo card? Tick it off! ‘Keirzo’ as the robot is affectionately known, will be performing as part of the computer music festival featured at Paramatta Lanes. From musical artists to art works - the festival will also feature the ‘Sky of Bubbles’ which features 50 spheres that light up at night and ‘Bloom’ which depicts the creative process symbolised by jellyfish.

Liveworks Festival by Performance Space runs from 19 - 29 October at Carriageworks with bucket loads of ticketed and unticketed undertakings that are way too many to list here so make sure to check out their websites. We are a huge fan of Rainbow Chan 陳雋然 so keenly looking forward to The Bridal Lament is an ambitious new performance and music project by the award-winning vocalist, producer and multi-disciplinary artist. Or maybe cLUB bENT bACK uP 9pm 28 October tickles your fancy?

Unticketed experiences to explore while at Carriageworks include Night 1001 an installation and live re-voicing of the last night of Barbara Campbell’s durational performance 1001 nights cast (2005–2008), Proof by Heidrun Löhr which draws on Löhr’s archive of more than 300,000 images to create a large-scale installation in the public space and ReelDance / Dance (Lens) with films from the archive in dialogue with new national and international films.

The Villain Era Tour is presented by Joel Granger in association with Hayes Theatre Co for one night only, Monday 2 October 7pm. A good private school boy from New Zealand to an egocentric Helpmann Award loser. Join Joel Granger for an evening of cabaret as he uncovers that his boy-next-door charm might be hiding his true diabolical nature. With credits including The Book of Mormon, Cry Baby and She Loves Me, enjoy Golden Age standards to contemporary music theatre to maybe even a brazen attempt at a pop song or two, if he’s feeling particularly villainous.

Hayes Theatre Co. will be delivering witty and deeply moving romance from 13 October with A Little Night Music. Welcoming back acclaimed director Dean Bryant (Sweet Charity, Assassins, Merrily We Roll Along), we’ve been waiting all year for this Sondheim classic. And there's even more excitement with Australian musical theatre legend (and theatre namesake) Nancye Hayes playing Madame Armfeldt, the production will also star Blazey Best, Melanie Bird, Jeremi Campese, Erin Clare, Kiana Daniele, Leon Ford, Dominic Lui, Pamelia Papacosta, Josh Robson and Erica Wild.

Join us from October 13 for this witty and deeply moving romance.

NEW South Eveleigh Street Party will take place throughout Sydney’s South Eveleigh in Locomotive Street, The Eveleigh and Village Square, over two days, Thursday 5 and Friday 6 October. As one of Sydney’s most significant historic sites, South Eveleigh will transform into a vibrant cultural hub showcasing a dynamic blend of entertainment and experiences that cater to all ages. Encounter headline acts Donny Benet and Ngaiire, as well as a line-up of Sydney’s best chefs, musicians and restaurants including Kylie Kwong’s Lucky Kwong, a collaboration between Matt Whiley’s Re and Alex Prichard of Iceberg’s Dining Room & Bar, and a special kids program presented by 107 Projects at Village Square and Anita Gelato. The event promises an unparalleled tapestry of experiences spanning music, food, beverage, art, design, dance, and play, embracing the myriad forms of community culture. At the heart of Street Party, Locomotive Street will come alive with giant inflatable tentacles that will extend from the buildings onto the street, and chalk artistry by local First Nations artists MadWings will transform the street into an urban canvas.

We couldn't talk about October in Sydney without mentioning the once only event on the 7th when Paul, Gene, Tommy, and Eric for what will be the biggest send-off party in the world for the band who gave us rock’n’roll! KISS The Final Curtain will bring down Accor Stadium.

The Surge a multi-layered feast of music, ideas, lessons from the past and hope for the decade ahead, brought to you by Ensemble Offspring and leading guitarists Andrew Blanch and Vladimir Gorbach, is touring NSW, Goulburn, Oberon, Parramatta, Wyong, Bundanon 6 - 15 October. Together, they reignite two '90s classics by iconic Australians Peter Sculthorpe and Nigel Westlake, alongside five recent commissions reflecting on the cultural, environmental and political situations Australia finds itself in today.

These thoughtful and engaging works – composed especially for The Surge by Aussies Robert Davidson, Felicity Wilcox and Jessica Wells – examine everything from human-induced climate change to the pervasive influence of the internet.

With stunning live visuals by the ever-inventive Peachey & Mosig, immerse yourself in poignant social revelations and shameless ’90s nostalgia!

9th Annual Wahroonga Food and Wine Festival returns to the picturesque Wahroonga Park on Sunday 29 October 11am to 5pm. With an impressive array of wineries from across NSW and Australia, the festival will also offer small batch distillers, Piggy & Moo's specialty Fried Chicken and Pork Belly Burgers, Berlin Bangers, Sofrito Paella, Asian Dumplings and Fish Cakes, Turkish Gozleme, Vegan Vege 4 Love food truck, the Satay Brothers, Cornstars Fritter Co, and an array of dessert food trucks, Hunter Valley Cheeses, Alexander Roastery Coffee, and Goose on the Loose, and an Artisan Producer Alley. Entrance is free.

Grill’d has cruised into Bondi Beach with its 166th national restaurant opening. To celebrate the opening, three local Bondi lifeguard legends, Harrison Reid, Ryan ‘Whippet’ Clark and Dean Gladstone will build their favourite Grill’d burger to battle it out for donations to their nominated charities. Guests that visit the Bondi restaurant can vote via the Grill’d Local Matters jars, a national initiative that gives back to local communities. Visitors can also order the burgers built by the boys!

Voting ends on the 31st of October, with a donation to the winner with the highest votes, and respectively to second and third.

Harrison's Burger Wagyu beef patty, crispy bacon, egg, aged cheddar, Spanish onion, lettuce, tomato sauce, herbed mayo

Charity: Live, Learn & Survive is an organisation with a vision is for every child and young adult, no matter their background or location, to have access to education on water safety, fire safety and first aid. Learn Survive has provided lessons to 26,000 children across 6 countries.

Ryan's Burger beef, cheese, pickles, lettuce, tomato with a special mix of mustard, mayo and BBQ sauce

Charity: Ocean Heroes is a platform for people on the spectrum to build confidence and social connection through surfing. Your donation would help us continue to provide a fun, healthy and unique way for people on the spectrum to improve their self-esteem.

Deano's Burger double beef, bacon, cheese, lettuce, avocado and relish

Charity: Waves of Wellness Foundation is a mental health surf therapy charity, committed to changing lives by delivering for-purpose, innovative support programs for people experiencing mental health challenges.

SXSW Sydney is on from 15 - 22 October with over 1,000 music, conference, gaming, tech and screen experiences to choose from, including 700+ speakers, 300+ performances, 170+ games demos, 200+ screen events, 1 huge Tech & Innovation expo and 1 week of free programming in Tumbalong Park. The full programme has now been announced on

Jewish International Film Festival graces Australian screens once again, presenting a curated collection of Jewish cinema's most enchanting and illuminating tales from across the world. Sydney screenings start this month from 24 October at Randwick Ritz and next month Roseville Cinemas. Featuring 55 Australian premiere films from 19 countries, the Festival will deliver a vast program; presenting 30 feature films, 20 documentaries, two series, and six short films alongside a suite of live events.

"In a world where stories are our bridge to understanding, this year's JIFF is a testament to the timeless resilience and adaptability of the Jewish spirit," said Jewish International Film Festival Artistic Director, Eddie Tamir. "As we celebrate a remarkable line-up of films, from the deepest roots of Yiddish culture to Australian stories and tales that push boundaries, we're honoured to curate this immersive journey, offering both a reflection on the past and a beacon for the future in the 2023 edition of JIFF."

Mental Health Month is celebrated in NSW each year in the month of October, and 10 October is the World Health Organisation, World Mental Health Day. There are many ways to support mental health and to increase awareness. Here's one way through the arts with a powerful, moving and joyful play, The Disappearance based on Kin Platt’s book The Boy Who Could Make Himself Disappear that meets mental illness and diversity with heart and with humour> The play opens for a two week Sydney season from 10 October at Chippen Street Theatre.

Spicers Guesthouse in the Hunter Valley are continuing BEYOND BLUE’s BIG BLUE TABLE concept to help raise essential funds to support mental health. Hosted by Beyond Blue Director and Hunter Valley local Johanna Griggs, guests will be treated to an incredible four-course lunch menu with matching wines on 22 October, by Jayden Casinelli, head chef of the Guesthouse’s éRemo Restaurant. A host of éRemo’s suppliers and other local businesses are donating ingredients, both gourmet and humble, to the Big Blue Table, as well as an impressive array of luxury auction items and experiences.

Images: Message In A Bottle credit Lynn Theisen.