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painter and professional photographer, was born in Van Diemen’s Land, son of John Richard Baily, steward to Bishop Francis Russell Nixon . Bailey went to England in 1861; Sketch to Windward (Crowther Library) was made on the voyage. Returning to Tasmania in the mid 1860s, he set up as a photographer in Hobart Town. According to his advertisements in Tasmanian almanacs and newspapers, he had trained at the London School of Photography. McPhail’s Directory of Tasmania for 1867-68 stated: 'H.H. Baily, (From the London School of Photography) vignettes, Cartes de Visite, and Miniature Portraits taken for Brooches, Lockets, &c., also Oil Paintings copied. Specimens always on hand.’
In 1866 Baily exhibited 'Album Portraits’ at the Melbourne Intercolonial Exhibition. He published stereo-photographs of landscape subjects in 1867 from his studio at 94 Liverpool Street, moving to 139 Elizabeth Street later that year. In 1874 some of his photographs were shown with the New South Wales Academy of Art; the Sydney Mail reported that his 'pretty collection of photographs, depicting Tasmanian scenery, chiefly in the vicinity of Hobart Town, elicited some attention’. In the same year he advertised in Walch’s Tasmanian Almanac : 'H.H. Baily… Prize Medallist Highest award for Album Portraits, Melbourne Exhibition 1866 1867. Enlargements, all sizes, finished in mezzotint, sepia or oil, with the greatest delicacy. A large selection of views of Tasmania from all parts of the Island.’
Baily advertised both photographic and oil portraits throughout the 1870s. He exhibited oil paintings (possibly on a photographic base) at the 1879 Sydney and 1881 Melbourne International exhibitions. He and his wife Celia Jane, née Bullock, had a son, Henry, who also became a photographer, so the firm continued in Hobart under the same name until 1918.