Pre contact – Members of Cadigal, or Gadigal, people inhabit Redfern, Erskineville and surrounds. The Gadigal Traditional Owners who today speak for the Sydney clan area stretched “from the south side of Port Jackson from South Head to Petersham”. The Gadigal people spoke the coastal Eora dialect of the Darug language and are often referred to as the Eora people. Redfern as a site was important to its people because it had a source of water – Shea's Creek, which today is Alexandra Canal, as well as a source of food from the wetlands that drained into the creek. Redfern’s high point on the terrain offered views of the trade route from Circular Quay to Parramatta, on which the colony’s first railway would be built. These trade routes connected with larger routes which linked the north and south, and east and west of Australia. Not only goods, but ideas, songs, ceremonies and news travelled along these routes.

The British arrive in January with catastrophic effect on the Aboriginal way of life. The Eora people do not flee, as Captain James Cook predicted, but stand their ground. Governor Phillip attempts to create good relations, but these soon disintegrate due to the persecution of the Aboriginals by the convicts. The Aboriginals are pushed out of Sydney town with fear of being shot, and with the quick pollution of the Tank Stream by tanneries, they are forced to use water sources near Redfern.

The smallpox plague devastates the Aboriginal people. Without immunity to the disease brought by the British, a large percentage of the Cadigal clan is wiped out. Following the plague, survivors from surrounding clans join together to survive, and to participate in the guerrilla movement led by Pemulwuy.

James Chisholm arrives in the colony of New South Wales aged 19 as a non-commissioned officer.

Settler David Collins observes Cadigal people performing a ceremony “between the town and the brickfield”.

In the early 19th century, the area that contains Redfern remains undeveloped, labelled as 'government paddocks', and becomes known as Cleveland paddocks after Governor Macquarie’s friend, Major Thomas Cleveland.

Circa 1817 major land grants are given to Dr William Redfern, William Chippendale and William Hutchinson.

Carters Barracks opens, which becomes the Sydney Female Refuge and later the Convent of the Good Samaritan.

The police barracks in Garden Street opens.

The Benevolent Asylum opens on the site where Central Station now stands. It is a refuge for homeless older men, deserted women and children, and the mentally ill.

Between 1823 and 1824, Cleveland House, 51 Buckingham Street, Surry Hills, is constructed for emancipist merchant Daniel Cooper. The design is attributed to Francis Greenway.

World's first railway, operating with steam locomotives, opens in England.

James Chisholm dies and is buried in the garden of Chisholm Estate and Calder House, until damage to the grave prompts relocation of his body to Camperdown Cemetery.

Grange Villa is constructed prior to 1840 at the western end of the North Eveleigh site. It is home to a number of prominent local and colonial figures, including William Beckett, Sir Saul Samuel and possibly Felix Wilson. It is purchased by the Department of Public Works in 1908 to expand the Eveleigh Railway Workshops, and probably demolished shortly thereafter.

During the 1840s, government legislation is passed ordering polluting industries to move from the Tank Stream. They move into Redfern and Waterloo, establishing industrial suburbs. Redfern develops terrace housing and villas.

On Hutchinson’s land, one of his sons-in-law, John Rose Holden, builds Eveleigh House. Named after Holden's mother whose maiden name was 'Everleigh', it stood on what is now known as The Block and is remembered by Eveleigh Street, which borders The Block.

Sydney Railway Act is passed. Sydney Tramroad and Railway Company is authorised to build the Sydney to Goulburn railway, and starts to build the first railway track in New South Wales, between Sydney and Parramatta – a distance of 22 km. The project runs into financial difficulty and is taken over by the New South Wales colonial government.

On 3 July, 10,000 people gather in Redfern to watch Mrs Keith Stewart, the daughter of Sir Charles Fitzroy, turn the first sod of earth for the construction of Australia’s first railway.

Cora Gooseberry, wife of Bungaree, is buried in the Presbyterian section of the Sandhills (Devonshire Street) Cemetery. Found dead on 30 July, E. Borton (or Berton) pays for her burial and headstone in the Presbyterian section.

On 16 August, James Sinclair Taylor McGowen is born aboard the ship Western Bride, prior to his family’s arrival in Melbourne.

Sydney’s first railway line, from Sydney to Parramatta Junction opens on the 26 September. It runs through the garden of the Chisholm Estate. Parramatta Junction becomes Granville in 1880, named after Granville Leveson-Gower.

J.F. Castles takes a lease over Chisholm Estate and Calder House on the Chisholm Estate and opens an exclusive school for boys.

Imported English rails, locomotive and carriages arrive in Sydney.

Railroads are nationalised by the government, after the privately owned Sydney Railway Company fails.

The first Redfern Station opens, on Cleveland paddocks. It is the first station in Sydney and includes the first Sydney railway workshops, called Redfern Railway Yard.

The Cleveland Street Overbridge is built.

Cleveland Street Overbridge is duplicated.

John Whitton is appointed NSW Railways Engineer-in-Chief.

Newcastle to Maitland railway opens.

The first national school opens in Redfern.

On 22 December the eastern portion of the Cleveland Paddocks was dedicated as a reserve for public purposes and named Prince Alfred Park in commemoration of the visit by the Duke of Edinburgh to the Australian colonies at the end of the 1860s.

J.S.T. McGowen’s family moves to NSW.

Mortuary Station is established.

The Metropolitan Workshops at Redfern Railway Yard are extended and planning for Eveleigh Railway Workshops commences.

J.S.T. McGowen joins the United Society of Boilermakers and Iron Shipbuilders.