Bondi’s cult-favourite dive bar, Chuck Trailer’s, is opened it’s second site in the heart of Sydney at 36 York Street this March.

Known for its high-energy atmosphere, extensive whiskey selection, and American-style menu, the two-storey venue is a fresh take on late-night dining and live music.

The ground floor will serve Chuck’s signature menu—smashed patty brisket burgers, loaded fries, and a diverse selection of wings—alongside a 6-metre bar offering 300+ American whiskies, craft beers, and cocktails. Downstairs, the basement has been transformed into a dedicated live music space, featuring a stage built into a custom concrete half-pipe. Expect a rotating lineup of rock, punk, and indie acts, with Birdman, Bare Bones, Rick Dangerous & the Silkie Bantams, and Neptune Power Federation already confirmed for opening weeks.

The venue’s design leans into its skate-punk roots, with murals by artists Steen Jones and Sindy Sinn, truck-bed booths, and walls covered in vintage Thrasher magazines. Owners Ben Campbell and Brendan Darcy describe the expansion as a natural evolution: “We wanted to bring the Chuck’s experience to the city while staying true to what made the original special—great food, strong drinks, and a no-frills approach to nightlife.”

Chuck Trailer’s CBD is operating daily from midday, with late-night service until 4AM from Thursday to Saturday. For updates, visit here.