Unbound Street Performance Festival brings two days of free circus, music, puppetry and unexpected theatre to The Rocks on 26 and 27 September. …

Chardy Party brings more than 100 wines and 30 winemakers to Sydney CBD for a long weekend afternoon of Chardonnay, food, music and conversation. …

Leon Bridges brings Happiness Anytime to the Sydney Opera House Forecourt on 26 February 2027, with 54 Ultra joining him for a summer night of soul and groove. …

The Hunger Games: Sunrise On The Reaping returns to Panem on November 19, following a young Haymitch into the 50th Hunger Games. …

SmartFone Flick Fest 2026 brings phone-made cinema from around the world to Sydney Opera House on November 1, with finalists spanning drama, comedy and documentary. …

Bryan Adams returns to Sydney in February 2027, adding a second Afterpay Arena show to his Roll With The Punches tour. …

Spring Cycle 2026 brings thousands of riders across Sydney Harbour Bridge on 11 October, with two routes linking the city to Pyrmont and Parramatta. …

As spring arrives in Sydney, A Room With A View brings E.M. Forster’s story of love, freedom and possibility to Belvoir St Theatre from 3 October to 1 November 2026. …

Street Paws Market brings dogs, families and local stalls together in Macquarie Park on 19 September for a free community day. …

Spirit Of Christmas 2026 brings the Willoughby Symphony Orchestra and Choir to Chatswood on 13 December for an afternoon of carols, classics and festive music. …