Early travelers and explorers who visited the Cape in the 1500’s traded with the Khoikhoi people who lived in the Greater Swellendam area. During the first half of the 18th century, Trekboers started drifting further away from the settled areas and the East India trading company started loosing control.

In 1743 Swellendam was declared a magisterial district, which makes it the third oldest district after Cape Town and Stellenbosch. In 1745 the district was named Swellendam after Governor Hendrik Swellengrebel and his wife, Helena ten Damme.

The Drostdy was built in 1747 to serve as headquarters for the landrost but a town soon started to develop around the Drostdy. The town soon became the gateway for travelers to the interior and the services the town offered became indispensible to these travelers and explorers.

In 1795 the burghers of Swellendam rebelled against the east India trading company and declared themselves a republic, but the glory was short-lived because of the British occupation in the Cape.

By the 19th century the Overberg was booming and Swellendam served as the capital being the most popular refreshment station. Today Swellendam is a popular destination for cultural and adventure tourists alike.