Sydney history walking tour, visiting Chippendale, city and Woolloomooloo

Brenden Wood
9 min readJan 27, 2024

Sydney is a city with a rich history, and after some excellent research by my two football mates, Mitch Stone and Andrew ‘Zappy Zapman’ Zapantis, I joined them for their 5 hour history tour of Sydney inner city.

Our history tour began at Wentworth Park in Glebe where rugby league was first played in 1908.

Brenden Wood, Mitch Stone and Andrew Zapantis at Wentworth Park. Picture: Brenden Wood

We visited the place where Warren Lanfranchi was shot and killed by Detective-Sergeant Roger Rogerson on 27th June 1981 in Dangar Place, Chippendale. We explored the link between the NRL and Daryl Somers’ Hey Hey It’s Saturday TV show and Chippendale. Why was Strickland Park not called Chippendale Park? The importance of Mortuary station in populating Rookwood Cemetery. We explore the history of Central railway station, Museum railway station and the J. F. Archibald Memorial Fountain. We complete the walk by visiting Macquarie Place, Harry’s Cafe de Wheels, St Mary’s Cathedral and the Pyrmont Bridge.

We recorded a podcast of our Sydney history tour, which we uploaded here.

Wentworth Park

Wentworth Park was named after William Wentworth, who was one of the founding fathers of New South Wales.

Wentworth Park in Glebe. Picture: Brenden Wood

A plaque outside Wentworth Park references the rugby league history that occurred at the location: “This site is recognised as being of great significance in the history of Australian Rugby League. Two matches were played at this site on April 20, 1908, the opening day of club rugby league in Australia, Easts beat Newtown 32–16, then Glebe beat Newcastle 8–5. The Glebe and Annandale premiership clubs subsequently used the venue as their home ground. Premiership football was last played here in 1931.”

Australian Rugby League’s plaque located at Wentworth Park in Glebe. Picture: Brenden Wood

Roger Rogerson shoots dead Warren Lanfranchi

Dangar Place is the laneway that was named after John Dangar who was a businessman and politician. Dangar Place is also home to the ‘X in a circle’ which is a marker that commemorates the spot where Roger Rogerson shot Warren Lanfranchi in 1981.

Zappy and Mitch searching for the X and the circle in Dangar Place at Chippendale. Picture: Brenden Wood

After spending almost 30 minutes, and referring to several online references, we managed to locate the X and circle that shows where Warren Lanfranchi was shot dead.

Following a lengthy search, Mitch Stone found the faint spot where Warren Lanfranchi was shot dead by Roger Rogerson. Picture: Brenden Wood

Lanfranchi was a heroin dealer who had served five years in jail for stealing colour TV sets. On 27th June 1981 Lanfranchi arrived at Dangar Place hoping to bribe Rogerson to avoid arrest on charges of armed robbery and attempted murder.

The X and circle marks the spot where Warren Lanfranchi was killed. It’s located in the gutter on the eastern side of Dangar Place. Opposite a fire stair well, in a ‘no parking’ zone. Picture: Brenden Wood

You can read more about what happened on that day on author John Dale’s website.

Strickland Building at Chippendale

Strickland Building was one of the first council-built housing projects in Australia and was opened in 1914. The building was built on top of one of the worst slum areas in Sydney. The Daily Telegraph reported that 160 applications were received for the 68 units that were created.

Strickland Building in Chippendale was designed by Sydney’s City Architect and City Building Surveyor Robert Hargreave Brodrick (inset). Photo: Brenden Wood

The Strickland Building was designed by City Architect and City Building Surveyor Robert Hargreave Brodrick, who held that title between 1898 and 1934.

Mortuary Station

Mortuary railway platform was opened in 1869 and is the oldest surviving railway station in Sydney.

The station is also home to the Mortuary Station clock, which is the oldest public clock in Sydney.

Sydney’s Mortuary Station. Photo: Brenden Wood

Goods Line Tunnel

The former Goods Line is a former freight railway line that connected an area at Central station known as the ‘Sydney Yard’ and the Sydney–Parramatta railway line to the shipping port of Darling Harbour. It was opened in 1855 and was extended to Dulwich Hill in 1922, providing a way for freight trains to access Darling Harbour without interfering with passenger trains.

The tunnel located near Mortuary station that was part of the Rozelle to Darling Harbour Goods Line. Picture: Brenden Wood

Central railway station

Central railway station opened in 1906. The site was officially opened on 4 August 1906.

Central railway station in SYdney. Picture: Brenden Wood

It is now the busiest railway station in Sydney and is one of the most iconic landmarks in the city.

Mitch Stone walking up to Central railway station. Picture: Brenden Wood

During our chat at Central railway station, which you can hear in this podcast, we discussed the importance of the distribution of exact time by the New South Wales railway network. Prior to the introduction of the first radio station in Australia in 1924, the only way for people in towns outside of Sydney to synch their watches and clocks was via the large clocks at railway stations, which were in turn synched by guards and rail staff who had synched their time pieces to the clock at Central railway station. Once AM radio stations began broadcasting pips at the top of the hour it allowed people the ability to set their own clocks and watches.

Before the introduction of AM radio railway clocks were important for people across New South Wales. Picture: Brenden Wood

The ABC’s Luke Wong wrote an excellent item about the importance of clocks and the railway network here.

Andrew Zapantis and Mitch Stone at Central railway station’s Grand Concourse. Picture: Brenden Wood

Macquarie Place Park

Macquarie Place Park is located at the corner of Bridge and Loftus streets, just south of Circular Quay. It is the oldest town square in Australia.

Macquarie Place Park. Picture: Brenden Wood

An obelisk was erected in Macquarie Place Park in 1818 by Governor Macquarie to mark the place from which public roads in the colony were measured.

Obelisk was erected in Macquarie Place. Picture: Brenden Wood

In Macquarie Place Park you’ll find an anchor and cannon from HMS Sirius.

Sir Francis Sutton salvaged the anchor in 1905 from the 1790 wreck of HMS Sirius on Norfolk Island and erected it in the park in 1907.

Zappy and Mitch at the anchor from the 1790 wreck of HMS Sirius on Norfolk Island. Picture: Brenden Wood

Near the anchor is the cannon from the same ship that was used as a signal gun at South Head from 1810, and joined the anchor in Macquarie Place in 1907.

Moore Steps at Circular Quay

Moore Steps steps were named after Sydney mayor Charles Moore, and were opened in 1868.

Moore Steps at Circular Quay. Picture: Brenden Wood

They’re located on the east side of Sydney Cove and lead up to Macquarie Street.

Harry’s Cafe de Wheels

Harry “Tiger” Edwards began selling pies in 1936, and after World War II he opened Harry’s Cafe de Wheels in 1945 with his cart located on Cowper Wharf Road in Woolloomooloo, near the Finger Wharf and Fleet Base East.

Harry’s Cafe de Wheels at Woolloomooloo. Picture: Brenden Wood

Speakers’ Corner in the Domain

Speakers’ Corner is located at the eastern side of The Domain, opposite the Art Gallery of NSW in 1878.

You’ll find some excellent historic information and photos after Speakers’ Corner here.

St Mary’s Cathedral

St Mary’s Cathedral was built between 1866 to 1928.

St Mary’s Cathedral. Picture: Brenden Wood

Underneath the cathedral is the crypt of St Mary’s Cathedral. Buried in the crypt are these people: John Bede Polding, Roger Bede Vaughan, Patrick Francis Moran, Michael Kelly, Norman Thomas Gilroy, James Darcy Freeman, Edward Clancy, Edward Cassidy, John Therry — first official colonial chaplain, John McEncroe — second official colonial chaplain, Daniel Power, Charles Davis — Bishop of Maitland and coadjutor bishop of Sydney and George Pell.

The crypt of St Mary’s Cathedral. Picture: Brenden Wood

The crypt at St Mary’s Cathedral is open to the public at certain times of the day. St Mary’s Cathedral is open every day, and admission is free.

“The Crypt is a breathtaking cavern of striking architecture and ornate design. It is highlighted by the magnificent terrazzo floor, considered to be one of the finest mosaic floors in the world. It was created by the Melocco Brothers, who introduced terrazzo flooring to Australia. The stunning Celtic cross inlayed in the floor of the Crypt is a striking feature 42 metres long by 21 metres wide. It is further adorned by five medallions depicting the days of Creation and on the stems and arms of the cross are 18 smaller medallions illustrating the titles given to Mary, the Cathedral’s namesake. The cross with its heady mix of complex swirls and geometric patterns in exuberant colours highlights the inspiration Peter Melocco translated from the Book of Kels, a manuscript of the gospels which traces its origins from the sixth to ninth centuries. The Crypt, first and foremost is a sanctuary; the resting place of some of our most important Australian Catholic leaders. From pioneer cleric John Joseph Therry to eight Sydney Archbishops the slabs placed above their graves are masterpieces in their own right with delicately written inscriptions outlining the highlights from the lives of the men who lie beneath. There are altars to remind one of its solemnity and sacred purpose and the altars, which like the floors, abound in rich symbolism. The base reliefs on the Polding and Kelly Memorial Chapel altars depict various scenes from Jesus’ life including His Passion. Though mainly known now as a stunning venue for art and liturgical exhibitions, music concerts, weddings and other special events, the venue remains a true artistic masterpiece”, says the St Mary’s Cathedral website.

Pyrmont Bridge, Darling Harbour

The Pyrmont Bridge is a heritage-listed swing bridge across Cockle Bay. It was opened in 1902. The bridge initially carried traffic via the Pyrmont Bridge Road between the central business district and Pyrmont.

Pyrmont Bridge. Picture: Brenden Wood

In 1981 the bridge was permanently closed to traffic and the government ordered the bridge to be demolished, but they later revoked this decision. In 1984 the Darling Harbour Authority was formed with the task of redeveloping Darling Harbour. The Pyrmont Bridge was restored, with the swing span in full working order, and incorporated as a pedestrian bridge in the redevelopment of Darling Harbour.

The opening of the Pyrmont Bridge. Video: Brenden Wood

A section of the monorail was built across the bridge at this time. The Pyrmont Bridge was reopened to pedestrian traffic in 1988.

Mitch Stone and Andrew Zapantis in Hyde Park. Picture: Brenden Wood
The war memorial in Hyde Park. Picture: Brenden Wood
Inspectint the indigenous artwork at the bottom of the new building called King & Phillip. Picture: Brenden Wood
Brenden Wood and Mitch Stone in Hyde Park, and the Archibald Fountain. Picture: Brenden Wood
Historic buildings at Broadway. Picture: Brenden Wood
An example of a low-set building on Shepherd Street in Chippendale. Picture: Brenden Wood

#Sydney #History