Pubs with History: 7 of Sydney's Most Unusual Drinking Dens

Established in the 1820s by ex-convict Samuel Terry, then rebuilt by brewery Tooth & Co. in 1921, the Fortune of War is the oldest continually licensed public hotel in Sydney. Over the centuries, the bar was considered the first and last stop for sailors and troops taking their own chances in the fortunes of war. Today, the Fortune is still in luck, with a range of local and imported beers on tap, a bistro, and live music five days a week. Combine your visit with a walking tour of The Rocks to learn more about the area's vibrant history.

Named after an English naval hero, The Lord Nelson is Sydney’s oldest continually licensed hotel. Built from sandstone blocks quarried by convicts from the base of Observatory Hill, it opened it to the public in 1841. Largely restored to its original state, the Lord is now home to an award-winning micro-brewery, bar, and restaurant. Tick if off your list along with other traditional taverns on a historical pub tour of The Rocks.

This mid-19th century pub is said to be haunted by the wife of a former publican, who broke her neck and died in 1849 after falling down the stairs in suspicious circumstances. The space is also notorious for its underground cellar tunnel, complete with convict shackles, which was used for rum smuggling and recruiting drunk patrons as sailors in the early days of the colony. The Hero is rich in history, heritage, and maybe even the odd haunting; if you dare, try a ghost walking tour to see more of Sydney's sinister side.

An iconic Sydney CBD hotel since 1885, the Edinburgh Castle hosted famed Australian writer, poet, and drinker Henry Lawson. It was here he wrote Star of Australasia and signed his first book deal for The Days When the World Was Wide. Lawson was part of the bohemian Dawson and Dusk Club, who were also regulars. The pub pays homage to Lawson and its colonial past throughout the bar, restaurant, and cocktail lounge upstairs. Just a 5-minute walk from the Queen Victoria Building, it's a convenient place to relax after a few hours discovering Sydney’s highlights.

If you find yourself in the trendy suburb of Paddington, the Woollahra Hotel is a short walk from Oxford Street and Centennial Park. In the 1880s, what was then known as Ackland’s Hotel was host to many macabre incidents, with its cellar offering perfect cool storage for the victims. The underground space remains largely unchanged—minus the bodies, of course— though the hotel above was rebuilt in the 1930s, restored to its former art deco glory. Today it's a local favorite, thanks to its bars, bistro, and fine dining offerings.

Former Australian Prime Minister Bob Hawke was almost as famous for his love of beer as his political talents. In 2017, he agreed to co-found Hawke’s Brewing with 100 percent of his royalties going to Landcare Australia, an environmental charity he helped create. Located inside Hawke’s Brewing, the Leisure Centre pays homage to 1980s pubs and the great man himself, with its wood paneling, Australian Chinese bistro, and memorabilia-filled pool room. And if craft brewing is your thing, there's even more to discover around Marrickville.

Not long after this Manly pub opened in 1859, a huge tide inundated the beachfront bar, washing the punters out onto the street. Four years later, a mysterious fire caused even more damage. The intrepid owner rebuilt the premises, only for it to be destroyed by fire again in 1923. The current heritage-listed brick building with its distinctive turret was built in the 1930s on the same site. Recently refurbished and boasting ocean views from its rooftop bar, this landmark Northern Beaches hotel is a great place to refresh after a couple of hours snorkeling in the local waters.