In 1901 Winkelmann left Queen Street wharf and set up his photographic studio in Victoria Arcade. His photographs were published in New Zealand periodicals and overseas publications. They were often successfully exhibited. At home he won the New Zealand Graphic photographic competition in 1895 and the Auckland Weekly News competition in 1908. Overseas his most notable award was the grand prix at the Panama–Pacific International Exposition in San Francisco in 1915.

Henry Winkelmann's photographs covered a wide range of topics. He photographed well-known individuals and their families and residences, workers and their workplaces, and significant events. His pictures sometimes showed humour, as in his portrait of Captain John Whitney at Wenderholm with a dog wearing spectacles. Perhaps best known for his maritime scenes, Winkelmann photographed yacht race days and often climbed the masts while sailing, for aerial pictures. He photographed New Zealand while on yachting, launch and steamer cruises and journeys throughout the country: in 1899 he travelled overland through swamp and bush from Whakatane to Rotorua. In 1903 he accompanied, as photographer for the Auckland Weekly News, a party of members of the General Assembly visiting New Zealand's Pacific islands territories. He was also photographer on expeditions to view solar eclipses at Flint Island in 1907 and 1908, Port Davey, Tasmania, in 1910, and the Vava'u group, Tonga, in 1911.

http://www.teara.govt.nz/en/biographies/3w25/winkelmann-henry