The earliest identifiable inhabitants of the Estcourt area were the San, a hunter-gather people, though rock engravings dating from four different Iron Age periods have been found on the farm Hattingsvlakte.

In the early nineteenth century the Zulu king Shaka used the Mfecane to build his empire, which led to a depopulation of the area.

[4] The first recorded settlement in the Estcourt area was in 1838 when a group of Voortrekkers encamped on the banks of the Bushmans River in anticipation of securing land right from Dingane kaSenzangakhona, the Zulu king.

Thus Natal acquired an English-speaking rather than an Afrikaans-speaking settler community and Estcourt, being so close to the Tugela River become a frontier outpost.

[6] On 4 January 1848 the Surveyor General recommended that the seat for the new magisterial district of Impofane be located at Bushmans River Drift.

The confirmation of large deposits of coal in the Dundee area in 1880, some 100 km north of Estcourt led to the building of a railway line to link the coalfields with Durban.

"[8] The mission station itself had been opened in 1892 - the second Augustinian Sisters establishment in Natal staffed mainly by French-speaking nuns from Canada and France.

Due to an economic depression after the war the school was unable to survive and the sanatorium had to complete with a nursing home that was run by one of the two doctors in the town.

Changing attitudes after Vatican II and the opening of hospitals run by the Provincial Departments contributed to the order closing its mission and the sanatorium in Estcourt in the late 1960s.

[9] In 1899, when he arrived at Estcourt as a war correspondent, Churchill described the town as "a South African town—that is to say, it is a collection of about three hundred detached stone or corrugated iron houses, nearly all one-storied, arranged along two broad streets—for space is plentiful—or straggling away towards the country".

[11] Estcourt effectively became the front[10] and this is where General Sir Redvers Buller first established his Natal headquarters and where Winston Churchill, then a war correspondent based himself.

On 15 November a raiding party ambushed an armoured train at Frere, 20 km north of Estcourt taking 70 prisoners including Churchill.

[12] After another raiding party was surprised on 23 November at Willow Grange,[13] 10 km to the south of Estcourt, the Boers withdrew to a position behind the Tugela River.

At some time close to the start of the twentieth century, Joseph Baynes, a Byrne settler and dairy industry pioneer, established a milk processing plant in Estcourt under the name of the Natal Creamery Ltd.[16] This factory was located adjacent to the railway station.

The factory was opened on 6 June 1918 by the Prime Minister General Louis Botha and marketed its products under the brand name Eskort.

The mill is in Estcourt, but its headquarters are in Durban and uses timber harvested from 21 922 ha of productive commercial plantations owned by the company.

[19] In 1963 the 58.5 million cubic metre Wagendrift Dam was constructed on the Bushman's River some 2 km upstream from the town of Estcourt.