Surrounding Whittlesea are 36 villages which make up the Hewu (meaning "flat land' in Xhosa) district.

Founded in 1849, Whittlesea was as a military outpost created to protect white settlers during the Frontier War of 1850–1853.

The town was named after Whittlesea in Cambridgeshire, birthplace of Sir Harry Smith (1787-1860), Governor of the Cape Colony from 1847 to 1852.

[3] Between 1948 and 1994, at the height of the apartheid regime in South Africa, Whittlesea belonged to the former Ciskei, a bantustan/homeland established in 1961 under the Promotion of Self-Government Act of 1959.

[7] However, projects started by The South African National Roads Agency Ltd (SANRAL)[8] and Expanded Public Works Programmes [9] have brought hope to the area.