The first European explorers of the area was a trading party led by a certain Ensign Shrijver, who were guided there by a Griqua via an ancient elephant trail in January 1689. The expedition reached as far as present-day Aberdeen before turning back and exiting the Klein Karoo valley through Attaquas Kloof on 16 March of the same year. However, it was only a hundred years later that the first farmers started settling in the region.
The first large permanent structure of the Klein Karoo, a church of the Dutch Reformed denomination, was first erected in 1839 near the banks of the Grobbelaars River. The village (and later town) of Oudtshoorn gradually grew around this church; it was named after Baron Pieter van Rheede van Oudtshoorn, who was appointed Governor of the Cape Colony in 1772 but died on the voyage out.
A small one-room school was opened in 1858, followed by the formation of a municipality and the founding of an Agricultural Society in 1859. During the same year work was also started on a larger church to replace the original small one.
Unfortunately, 1859 also signalled the start of a long and serious drought which severely depressed the national economy - by 1865 there was serious poverty. When the drought was finally broken by floods in 1869 the depression lifted and Oudtshoorn was transformed from a struggling village to a town of great prosperity.
The main reason for the large rise in prosperity was the ostrich, whose feathers had become extremely popular as fashion accessories in Europe; they were especially popular for use on hats. Between 1875 and 1880 ostrich prices reached up to GBP 1,000 a pair. The farmers of the region, realising that ostriches were far more profitable than any other activity, ripped out their other crops and planted lucerne, which was used as feed for the ostriches. The rising wealth also finally allowed for the completion of the Dutch Reformed Church - it was opened on 7 June 1879.
Owing to overproduction, the ostrich industry experienced a sudden slump in fortunes in 1885; the town's misery was compounded when it was hit by severe flooding during the same year, which washed away the nearby Victoria Bridge which had been built over the Olifants River only the year before.
The Oudtshoorn of today is a large and modern town that relies mostly on tourism, farming and the ever-present ostrich industry for most of its economic activity. The Klein Karoo Nasionale Kunstefees ("Little Karoo National Arts Festival"), South Africa's largest Afrikaans language arts festival, also takes place in the town on a yearly basis.
Tourist attractions in Oudtshoorn and the surrounding areas include: