History of convict colonial settlement from the beginnings of the First Fleet in 1788, and other significant parts of Old Sydney Town's heritage.
Stand at The Gap and the ocean is suddenly right there — no harbour, no ferry, just Tasman swell chewing sandstone. This is the seaward cliff on Sydney’s South Head, near Watsons Bay, reached from Old South Head Road. The headland has long been a coastal landmark for ships approaching Port Jackson — and a place of tragedy when vessels mistook the cliff line for the harbour entrance in bad weather.
On the night of 20 August 1857 the clipper Dunbar, inward-bound from England, was wrecked on the rocks south of the Heads near The Gap. One hundred and twenty-one passengers and crew died; the sole survivor was seaman James Johnson, found clinging to the cliff days later. The disaster stunned colonial Sydney: a huge funeral procession moved through the city, and the wreck helped spur construction of Hornby Lighthouse at the tip of South Head to mark the true harbour entrance. An anchor memorial at The Gap (established 1930 from Dunbar material recovered in 1910) and a historic rock inscription form part of the State Heritage-listed Dunbar Group, together with the underwater wreck remains.
Treat “It is Our Painful Duty” as a period quotation or image caption if that is what the photograph shows — not as unexplained body text.
The harbour view from Watsons Bay is the one on the postcards North Head opposite, Tasman out the Heads — but the place-name is a working one. Robert Watson (c.1756–1819), quartermaster of HMS Sirius in the First Fleet, later dockyard boatswain, pilot and harbour master, is the Watson in the bay. Governor Philip Gidley King granted him land at South Head in 1801; after the South Head Road opened, Governor Macquarie visited his stone house in April 1811, appointed him senior pilot (harbour master followed), and the Sydney Gazette was already calling the locality Watson’s Bay.
Watson was dismissed from dockyard posts in 1816 after a misconduct case, then appointed first superintendent of the new Macquarie Light at South Head in November 1818. He died the next year. A commemorative seat in Robertson Park (1929) summarises the career — useful locally, though some inscription details are simplified. The suburb later became famous for cliff walks at The Gap, pilot and signal stations, HMAS Watson, and the ferry from Circular Quay. Harbour panoramas “from Watsons Bay” sit in that longer story of navigation, wreck prevention and waterside settlement at the Heads.
Drive or ferry up the coast and the silhouette that says “Newcastle” is Nobbys Head — dual-named Whibayganba for the Awabakal people — the distinctive rock at the southern entrance to the harbour. Europeans first knew it as an island (also Coal Island). Governor Lachlan Macquarie laid the foundation stone for Macquarie Pier on 5 August 1818 to tie it to the mainland and tidy the entrance; convict and later free labour worked the pier for decades. It was completed in 1846 and later rebuilt as a stone breakwater. Sand piled along the wall, made an isthmus and Nobbys Beach — so the former island now reads as continuous headland.
In the 1850s the crown was lowered for a lighthouse and signal station platform. Nobbys Head Light (under colonial Government Architect Alexander Dawson) was finished 1857–58 — among the earliest permanent lights on the NSW coast after Macquarie Light at South Head. The lighthouse sits in Newcastle’s civic imagery and coat of arms. Views “from the Nobbys” look across the working coal port that grew from a penal outpost into one of Australia’s great harbour cities.
Drive out to Windsor and the concrete high-level span over South Creek looks like any modern creek crossing — until you realise this is about the fifth go at getting people from McGraths Hill into town without swimming. European settlers needed a reliable crossing here from the earliest Hawkesbury farms. Andrew Thompson built a floating bridge about 1802 and collected tolls; John Howe’s log bridge (Howe’s Bridge) followed about 1813. A wooden arch named for Governor Sir Charles FitzRoy replaced earlier structures in the mid-nineteenth century — local histories commonly date that span to 1848.
Then came iron. D. & W. Robertson supplied the ironwork and G. H. Royce is associated with construction of the 1879–1881 Fitzroy Bridge, opened to traffic in early March 1881. The present reinforced-concrete high-level bridge is mid-1970s (opened 1974/1975 in Hawkesbury accounts). Tucked beside the crossing is the 1835 Toll House — one of only two intact toll houses left in New South Wales — rebuilt after the 1864 flood and restored externally in the 1990s.
Historic photographs here likely show an earlier Fitzroy span (timber or iron), not the modern concrete bridge. Caption by era if the date is known; otherwise say “historic view.”
If you drive out to the Hawkesbury and come into Richmond along Windsor Street, St Peter’s sits on the rise above Pugh’s Lagoon as if Macquarie had planted it there — which, in a way, he did. This is one of his five Macquarie Towns. On the Hawkesbury tours of 1810–11 he chose an elevated bank for church, schoolhouse and burial ground; on 10 January 1811 the site was marked out with strong posts. An early schoolhouse-chapel served the town until a purpose-built church was needed.
The present Colonial Georgian church was designed by Francis Clarke and built by James Atkinson between the later 1830s and 1841. Bishop William Grant Broughton consecrated it on 15 July 1841. The picturesque rectory, also by Clarke, was completed in 1847. Edmund Blacket later altered the church — porch 1850, chancel mid-1850s — and remodelled the rectory in 1863. The group — church, rectory, school hall, cemetery and stables — sits in a park-like setting overlooking the lowlands and is listed on the NSW State Heritage Register.
Photographs here show the Richmond church and rectory group in the Hawkesbury landscape. This is St Peter’s, Richmond (Hawkesbury), NSW — not St Luke’s, Richmond, Tasmania.
King Street cuts east–west through the CBD — Domain / Macquarie Street at one end, the land falling toward Darling Harbour / Cockle Bay at the other — named for Philip Gidley King, First Fleet officer and Governor of New South Wales (1800–1806). Nineteenth-century “looking west” views catch shopfronts, hotels and horse traffic on the descending ridge — the commercial grain between George, Pitt, Castlereagh and Elizabeth.
The street stayed a retail and theatre-adjacent corridor well into the twentieth century, rebuilt after fires and boom cycles. Images here belong to that looking-west documentary habit rather than to one surviving landmark façade. Caption by identifiable corners, signage or vehicles where you can read them — and don’t confuse this CBD King Street with Newtown’s King Street.
