The place was known to the Herero under the name Otjivanda. In 1885, 40 Boer families from the north-west of South Africa settled at Grootfontein. Part of the Dorsland trekkers, they were heading towards Angola. When that territory fell under Portuguese control, they turned back and established the Republic of Upingtonia at Grootfontein. Abandoned by 1887, it became the headquarters of the South West Africa Company in 1893.

In 1908 the Roman Catholic church established a mission in Grootfontein as the basis of their eventually successful attempt to establish missions in Kavango.

Like all the towns in the Otavi Triangle, Grootfontein is green in summer but drier in winter. In spring, jacaranda and flamboyant trees bloom in profusion. The town has an old German Schutztruppe fortress from the year 1896, which today houses a museum that expounds on the local history. The economic mainspring of the area were for many decades the Berg Aukas and Abenab mines to the north east of the town. These produced zinc and vanadium but have since closed. This is dolomite country and the carbonate deposits in the upper parts of the mine have yielded interesting fossils of simian or pongoid creatures that lived millions of years before modern humans evolved.

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