Walk among heritage buildings and sites that were established in Sydney's colonial past and you will hear plenty of engaging stories from your tour guide along the way.
And the tour is a good way to get a cardio workout without even realising it!
The Starting Point (Hyde Park)
Meet at the Archibald Memorial Fountain in Hyde Park and look for tour guides wearing an orange shirt. But be aware that there is also a bus tour that meets at the same site so ask which guide will lead the walking tour.
The Archibald Memorial Fountain is located just a 5-minute walk from St James Railway Station (or a 10-15 minute walk from Town Hall). It's a statue designed by French Artist Francois-Leon Sicard in 1926 honouring the partnership between France and Australia during World War I.
During the early 19th century, Hyde Park was used by convicts to play sporting games as well as by the Australian Army who shared the grounds for drill training exercises. Convicts played Cricket, Rugby and Hurling on the site and they also used the terrain for Horse Racing.
Before you start to walk, your guide will point your attention to St Mary's Cathedral Church which is located across the road from Hyde Park. Originally built in 1821 (and re-built in 1865 after a fire destroyed its structure), it was the first church built in the new colony by former Governor Lachlan Macquarie.
Your guide will inform you that a new feature was added to the cathedral in 2000 (and you wouldn't be able to tell given that the feature blends in so well with the rest of the Cathedral's 19th-century Gothic design).
Lachlan Macquarie: The Town Planner
The tour leaves Hyde Park and moves down Macquarie Street within the Sydney CBD. Statues of Lachlan Macquarie and his wife Elizabeth Macquarie are placed near the corner of St James Road and Macquarie Street.
Former Governor Lachlan Macquarie held office between 1810 to 1821 and developed the town plan for Sydney. He named Macquarie Street after his family name and Elizabeth Street after his wife Elizabeth Macquarie's name.
Learn the legacy that his name has left upon the city from your tour guide.
Visit the Hyde Park Barracks that housed up to 1,400 convict men and boys at one time. The barracks were built to monitor convicts and ensure that they were well behaved during their time in the living quarters.
The Hyde Park Barracks were built in 1819 and closed in 1848 converting into an asylum for women up until 1887.
Across the road from the Hyde Park Barracks lies the oldest church building in Sydney. Built in 1824, St James Church was used by the convicts on Sundays as a place to worship and pray. Churches were built in an attempt to bring morality back into the convict community. But these efforts were mostly in vain as you will find out later in this article.
The Rum Hospital
The Mint (South Wing)
Your guide will walk you further down Macquarie Street to The Mint which was the South Wing of the former Rum Hospital. Convict patients were treated within the hospital from 1816-1848. After it's closure, the South wing was converted into a mint that printed coins from 1854 to 1926.
Many of you might be curious about why the building was nicknamed 'The Rum Hospital'. Well to put it simply, Governor Macquarie made a deal with three merchants over the ownership of imports of rum and spirits into the colony. In exchange, the merchants agreed to build the hospital.
If you do choose to attend the Sydney Walking Tour, you will also learn why The Rum Hospital was poorly designed (and it's a head-scratcher!). Without giving too much away, let's just say that the design of this wing would have made life extremely difficult for patients, staff and visitors.
Rub the bronze snout of a life-sized statue of a wild boar and drop a coin into the boar's mouth (letting it drop into the pool of water beneath). It is believed that this gesture will bring you good fortune and the money donated will go to the Sydney Hospital.
Gifted to Sydney in 1968 as a replica of the original statue in Italy, Il Porcellino sits outside the Centre Wing of the former Rum Hospital (now known as The Sydney Hospital).
Old Parliament House (North Wing)
The North Wing of the former Rum Hospital was converted into the first NSW Parliament House in 1829 where the first Legislative Council met for Council meetings. Legislative Council meetings moved between the various rooms of the North Wing because the Council needed to find bigger rooms (as the number of members grew from year to year).
Armed with security guards who patrol the outside of the building, the Parliament House of NSW continues to be used to this day by the NSW State Government where the Legislative Council (Upper House) and the Legislative Assembly (Lower House) regularly meet inside the Chambers.
It should be noted, however, that the tour does not go inside any of these three wings of the Rum Hospital due to time constraints.
Matthew Flinders was an English Navigator who led the first trip around the island of Australia. He was also the first man to assign the name Australia specifically to the continent (and island) itself after he saw the name being referenced in numerous books.
Visit his statue on Macquarie Street with the Free Sydney Walking Tour and learn the sad story of Matthew Flinders' life. Your guide will also share with you the peculiar name that was being considered as an alternative option for naming the continent.
It's a peaceful place away from the hustle and bustle of the CBD. Although the tour only gives you a glimpse of a small part of the garden, you can always return at a later time and really soak in the serene atmosphere.
Site of the Governor's Residence
The Sydney Walking Tour then moves into Bridge Street approaching the site where the First Government House had been built.
Depiction of First Government House (By John William Lewin (1770-1819) - Series 01: Australian paintings by J.W. Lewin, G.P. Harris, G.W. Evans and others, 1796-1809, held at the National Library of Australia, Public Domain,https://commons.wikimedia.org/w/index.php?curid=17959431)
Constructed in 1788 by Captain Arthur Phillip (who was the very first Governor of NSW), the house was the first major building to be built on the Australian Mainland. English Bricks and Stones from the local area were used by convicts to build the Governor's residence and office. Originally designed with six rooms, successive governors renovated and added extensions onto the Government House in later years.
Most of the house was demolished in 1846 but the remaining structures of the building are displayed at the Museum of Sydney which rests on the original site of the First Government House.
The Edge of the Trees
Gaze upon the art piece The Edge of the Trees made by artists Janet Laurence and Fiona Foley.
Edge of the Trees reflects the first interaction between the English Settlers and the Aboriginal Natives. The trees symbolise how the Aborigines watched the English settlers arrive on shore from behind the trees.
Walk up to the pole tree structures and read the Aboriginal words placed upon the trees.
The History of Bridge Street
Before the tour moves into Loftus Street and heads down to Circular Quay, your guide will show you the historic building currently used by the NSW Department of Lands and you will also learn why Bridge Street was given its name. A bridge used to go over The Tank Stream which was a canal that ran from Hyde Park into the Harbour. The stream is located at the dip of two hills (right near where Pitt Street intersects Bridge Street).
Convicts used the stream to collect drinking water until 1826 when the water supply became polluted due to increased farming and infrastructure projects within the area. A stone grating was placed over the top of the canal in 1858.
Ask the tour guide if they may be able to take the group down to the spot where the bridge used to be.
The Sydney Walking Tour moves down Loftus Street and meets at the front of Customs House. This building served as the Headquarters of the Australian Customs and Border Protection Service for nearly 150 years.
Customs House opened in 1845 to manage the inflow of new settlers due to increasing trade within the area.
Walk into the foyer of Customs House and take photos of the model replica of the Sydney CBD placed beneath the glass floor.
It was believed for a long time that the site of Customs House was the place where Captain Arthur Phillip raised the Union Flag in 1788 to signify the creation of a new colony. But this long-held belief turned out to be false and the Sydney Walking Tour finishes at the real location where the flag was raised.
Moving underneath the Cahill Expressway, your guide will take you into Circular Quay. Take some photos of the Sydney Opera House and the Sydney Harbour Bridge and really see Sydney in the eyes of a tourist. Your guide will also point you to the coffee shop that has the best view of Sydney Harbour.
Explore The Rocks on the Sydney Walking Tour and discover the area's colourful history. It's easy to feel like you have stepped back into the 19th century as you walk among the vintage buildings and houses in the area.
Many convicts flocked to The Rocks setting up a community of 1,200 people by 1823. Meanwhile, government officials and wealthy aristocrats retained their residence in the areas near Hyde Park and The Tank Stream. These were two communities who lived very different lifestyles.
A number of brothels and pubs were built in The Rocks and the area quickly developed a reputation associated with mischief and debauchery. Convict men who lived in The Barracks spent their Sunday afternoons in The Rocks (after attending church) and often got up to mischief.
Gangs were soon established around the area which included the infamous The Rocks Push who were larrakins that were granted membership through bare-knuckle boxing matches. Female members of the gang lured men who were drunk or were under temptation into secluded areas where these men were then assaulted and robbed by members of The Rocks Push.
You will also learn on the tour how cramped the living conditions really were for many families who lived in the area.
Sydney's Oldest Pub
Fortune of War is Sydney's Oldest Pub serving rum and wine to convicts, merchants and patrons. Convict Samuel Terry built and opened the pub in 1828 and the building has retained most of its 19th-century charm.
Although the tour does not go inside the pub, you may stop by and have a drink on your way back from the tour.
A web of hidden passageways lie all around The Rocks area including the Suez Canal. It was once known as a hot spot for debauchery because members of The Rocks Push regularly lurked and assaulted their victims in this spot.
Take a stroll along Atherden Street in The Rocks which is one of the final stops of the Sydney Walking Tour. Atherden Street is just 28 metres long and ends at the face of a former quarry. What also gives the street its unique charm is that the road surface itself is comprised of lines of bricks.
View of Sydney Harbour Bridge from the Pylon Lookout
Finishing at the Pylon Lookout (located next to the Overseas Passenger Terminal), you can soak in the best panoramic views of Sydney Harbour.
The Sydney Walking Tour also ends on the site where Captain Arthur Phillip planted his Union Flag into the ground. The exact spot rests beneath the Overseas Passenger Terminal.
Handy Tips and Final Thoughts
Here are a few handy tips for you to know if you do decide to go on the Sydney Walking Tour;
1) Although the tour is deemed to be free, you may choose to make a donation if you wish. But it is entirely up to you how much you would like to pay. Most people on the tour that I had attended donated between $10- $30 per person.
2) Bring a bottle of water with you especially on hot days.
3) Mention to the tour guide that there are tunnels, bunkers and an underground lake located beneath the Sydney CBD. It may encourage your tour guide to talk about the history buried beneath the city and will make the tour even more compelling for you and the rest of the group.
So treat yourself to a tour of the heritage buildings around the Sydney CBD and The Rocks and see Sydney in a new light. It's a city with an intriguing past that is waiting to be unearthed and explored.