Henry Winkelmann emigrated to New Zealand in 1878, at the age of 18. He had his first experiences of sailing on the ninety-day voyage aboard the Calypso, enduring storms, climbing the rigging and learning the customs of the sailors. Winkelman worked his way from Dunedin to Auckland on a series of ships, and by 1881 was living in a boarding house in Hobson Street. He and a fellow boarder named Hudson agreed to spend three months on uninhabited Jarvis island, the minimum time required to claim it for the Henderson and Macfarlane Shipping Company; the island was a source of valuable guano, but was so remote that it had been abandoned some years prior. After nearly eight months on the island, their supplies exhausted save for rainwater, birds’ eggs and fish, Winkelmann and Hudson were rescued, and were paid only the wages agreed upon, in spite of their ordeal.
Winkelmann joined the Bank of New Zealand as a clerk in 1882, and was transferred several times during the next decade, working in Fiji and Australia. He was highly musical, and supplemented his income from the bank by teaching the zither, an instrument at which he had been proficient from a young age. In 1892, Winkelmann recorded in his diary the purchase of a Lancaster Instantograph camera, with which he also began to earn money for taking photographs. At this time, Winkelmann was living with his mother in Devonport, Auckland, at 14 Dock (now Huia) street. Between 1892 and 1901, Winkelmann worked at a variety of jobs, including as a customs agent, insurance salesman and debt collector, and director of the Coastal Steamship Company. Throughout this time, he continued to take and sell photographs.
Although Winkelmann is best known for his yachting subjects, being himself a passionate sailor, he travelled widely throughout the country during the 1890s, and built up a substantial body of photographs, including street scenes, industrial subjects, portraits, panoramas and landscapes. Winkelman’s photography was widely published at the time, and in 1901 he cemented his reputation as one of the country’s leading photographers by establishing a studio in Victoria Arcade, Auckland. Winkelmann’s work was included in the Christchurch International Exhibition of 1906, and he was the photographer on two scientific expeditions, to the Flint Islands in 1907-8 and to the Cook and Society Islands in 1910. In 1913, Winkelmann purchased a property in Kaukapakapa and retreated there for the duration of the First World War, perhaps due to anti-German discrimination. He remained reclusive for the remainder of his life, only emerging for yact races. Winkelmann’s glass plate negatives, as well as a number of his prints, are held by the Auckland Museum.