Historical tours of The Rocks in Sydney bring colourful convict tales to life

Wherever you are in the city of Sydney, you don’t have to look very hard to catch a glimpse of the city's colonial past. It’s present in the foundations of buildings, street and place names, parks and gardens, and of course, preserved historic precincts like The Rocks. This popular historical walking tour shares the story of the early colony with guests. Review: Barry Johnson

Historical tours of The Rocks
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These small group historical tours of The Rocks precinct will bring colonial Sydney to life. Convict Trails and Adventures is a two-hour guided walk that takes in many of the historic points of interest in and around The Rocks and harbour-side inner city.

Tour name: Convict Trails and Adventures
Runs: Daily (depending on numbers)
Departure point: Customs House, 31 Alfred Street, Circular Quay
Departure time: 10am
Duration: 2.5 Hours (approx.)
Inclusions: Guided walking tour and commentary

Best price guarantee: If you find this tour elsewhere at a cheaper price, we will beat it by 10%. Some conditions apply. There are no booking or credit card fees when you book this tour with The Big Bus tour and travel guide.

When Arthur Phillip led a band of convicts to colonise Australia, a new genre of urban tales, taller than the masts of the tall ships of the First Fleet, was born.

Many of those stories are shared by Go Local Tours on their two-hour historical tours of The Rocks precinct and surrounding areas of inner-city Sydney.

We meet on the steps of Customs House at Circular Quay for this morning walking tour, titled Convict Trails and Adventures. Queen Victoria’s frosty stare, immortalised in a stone bust above the entrance archway, lightens as our cheerful guide John begins his commentary. Since he was ‘knee high to a grasshopper’ (colourful colloquialisms feature heavily on this tour!), John has explored Sydney, sharing its secrets with keen visitors.

Australian and Aboriginal flags flutter overhead as John takes us back in time, with lively tales of 40,000-year-old Mungo Man; his recently rediscovered remains offering fascinating insights into ancient Indigenous spirituality.

Historical tours of The Rocks

Historical tours of The Rocks: Customs House. Image: Bigstock

As they stepped ashore in 1788, British convicts were mistaken by local Aboriginal groups as returning spirits. The new arrivals encroached further inland, until clashes drove the first inhabitants from The Rocks and they were replaced by the new colony.

Rum wars, farming disasters, rogues, heroes and Lady Chatterley’s Lover star in a rapid-fire history lesson, while we sip coffee and imagine horse-drawn carts trotting through streets lit by gas lamps.

Standing over the scale model of Sydney within the floor of Customs House, we straddle George Street, the grand boulevard that originally split the city, separating rich colonials and poor convicts. Two centuries later the East/West divide remains, with property prices continuing to skyrocket in the exclusive eastern suburbs.

Historical tours of The Rocks

Historical tours of The Rocks. Image: Barry Johnson

In their new home, many convicts built new lives, including Francis Greenway who was transported for forgery before becoming the colony’s official architect. After designing St James’ Church, he continued to tempt fate and died bankrupt, but nevertheless became the only forger in our history to be honoured on official currency.

Turning into cobblestoned Bulletin Place, we pass the former printing presses of the Bulletin magazine, first published in 1880, and still perhaps echoing with the touts of the editor, selling copies from his soapbox.

Historical tours of The Rocks

Sydney’s colonial past exists side by side with modern city life. Image: Bigstock

Next stop on these historical tours of The Rocks, Harrington St, where we see the spire of one of Sydney’s oldest sites of Catholic worship, St Patrick’s Church, which has stood since the 1840s. Religious heritage and city revelry often mix in modern Sydney, and a former convent school adjoining St Patrick’s is now home to the Heritage Belgium Beer Cafe.

At the exposed colonial archaeological site, The Big Dig, a crude well held a clever convict’s secret (and illegal) alcohol stash.

Historical tours of The Rocks

Historical tours of The Rocks. Image: Barry Johnson

We emerge from a tunnel at Observatory Hill, where southern constellations enthralled our first astronomers. Today it’s the endless patterns of the Harbour Bridge’s crisscrossing girders that hold our gaze.

While the Red Coats no longer march through Millers Point, the Garrison Church still harks back to its military heritage, adorned with the emblems of the Commonwealth’s finest regiments.

Historical tours of The Rocks aren’t complete without a visit to a couple of the precinct’s oldest pubs, but beware of free drinks. Naive colonial travellers were given free rum at the Hero of Waterloo until they collapsed drunk in the basement. Carried out via a secret tunnel, they often woke aboard a ship to endure months of hard labour at sea.

Historical tours of The Rocks

Historical tours of The Rocks. Image courtesy of Hero of Waterloo

Foundation Park teases visitors with a glimpse of the docks. Here, desperate wives once prayed for their husbands’ safe return from dangerous whaling expeditions. In the park, the claustrophobic convict homes still stand, the low roofs giving us temporarily hunched backs.

From here we descend into the entertainment precinct of The Rocks, which has bustled since the first days of the colony. Stories of our colonial ancestors fuel animated chatter over a coffee or tea to end the tour.

For a colourful introduction to the city’s earliest stories, these historical tours of The Rocks are ‘grouse’!

Barry travelled as a guest of Go Local Tours.

Additional images: Bigstock


Barry Johnson

About the writer

Barry Johnson is a freelance writer living in Sydney, but with a trail of Aussie souvenirs scattered throughout previous homes in Europe, America, Asia and the Middle East. Barry believes travelling is an adventure where the highlights push you on to the next trip and the lowlights can be laughed at with hindsight. Without a passport, he’d have missed getting lost in the Californian forest a week after the Blair Witch Project went viral, building a giant Buddha on a Cambodian mountain, camel racing in an Egyptian desert and teaching English to Peruvian children as they taught him Quechua, the language of the Incas.

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