Sydney is Australia’s oldest city, meaning centuries of the country’s history have unfolded in its streets. From ancient Aboriginal art to blood-curdling convict settlements, step back in time while learning about these historic sites found around the Harbour City. Did you know – Culture Trip now does bookable, small-group trips? Pick from authentic, immersive Epic Trips, compact and action-packed Mini Trips and sparkling, expansive Sailing Trips.
Susannah Place Museum
The Rocks was one of the very first places the British colonised when the First Fleet sailed into Sydney Cove to establish a penal colony in 1788, and this museum offers an insight into what the nascent city was like in those early days. Susannah Place — four humble terraces built by Irish immigrants in the 1840s — have survived redevelopment over the last two centuries, providing a glimpse into everyday life during convict times.
There are 14 islands in Sydney Harbour, but none are as gruesome as the one known as ‘Pinchgut’ for the brutal conditions that prisoners faced there. British colonisers installed a gibbet (or hanging gallows) in the late 18th century — leaving convicts to hang there for years as a warning to potential crooks — before building Australia’s only Martello fortress there about 60 years later. These days, you can catch the ferry to Fort Denison… just keep an eye out for skeletons.
On the other side of the Sydney Harbour Bridge sits the largest island in the harbour, which also has a long convict history. The UNESCO Heritage-listed Cockatoo Island was used as a convict penal establishment between 1839 and 1869, then became one of Australia’s biggest shipyards until 1991, using docks built by convicts in the 19th century. Today, you can camp the night on the island with jaw-dropping front-row seats of Sydney Harbour.
It’s important to point out that Sydney’s history didn’t begin when the British rocked up to colonise the territory in the late 18th century — Indigenous people had occupied the Australian continent for the prior 60,000 years. Evidence of the longest continuously surviving culture on Earth is found at Grotto Point on Sydney’s Northern Beaches, which is home to a series of rock engravings of kangaroos, whales, and boomerangs made by the local Aboriginal population.
The Lord Nelson Brewery Hotel
The Lord is proud of its title as Sydney’s oldest continually licensed hotel, pulling beers non-stop since way back in 1841. A plasterer named William Wells converted his home into a three-storey sandstone hostel in the 1840s and the pub has remained in its original skin ever since, benefitting from significant renovations and the addition of a brewery in the 1980s and 90s. The Hero of Waterloo, Fortune of War, and Australian Heritage Hotel are other historic pubs for a tipple in The Rocks.
Hyde Park Barracks
Located smack bang in the middle of Sydney’s inner-city, this historic site has gone through many lives — first as spartan accommodation for convicts, then as an immigration depot for female settlers, and finally used for courtrooms and government offices. In 2018, Hyde Park Barracks is a compelling museum tracing this chequered history, sitting on the UNESCO World Heritage list as one of the most significant convict sites in the world.
Sydney Cricket Ground
Scour the globe and you won’t find many sports stadiums still in use that stretch as far back as the SCG. Cricket has been played on the site since the early 1850s, and over the last century and a half, Sydney’s favourite sports venue has hosted nearly every sport under the sun, including more than 100 cricket Test matches in front of its gorgeous Heritage-listed Members Pavillion.
The town of Ebenezer on the northwest outskirts of the city boasts the oldest surviving church in Australia. The church was established by the local Protestant community in 1809 and was also a pioneer of education in the convict colony, opening a school as early as 1810. Visitors are welcome to tour this historic religious site, including the cemetery and churchyard attached to the church.
Museum of Sydney
Want to learn more about the city’s fascinating history? Plan a trip to the Museum of Sydney. This super modern museum is built above the remains of Australia’s first Government House and on the site of the first contact between the Indigenous Gadigal people and the British colonisers, and houses archaeological relics of Sydney’s early settlement.
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