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Born at Middleton Junction, Jackson had relatively little formal training. After leaving school, he attended evening classes at Oldham School of Art. It was here that he first came into contact with young members of the Manchester School, who were attracted to the work of the Barbizon painters. He was made a member of the Arts Club in 1879 and after the exhibitions of the Manchester Academy in 1880 and 1881 he was made a member of the Manchester Academy of Fine Art. He became a member of the New English Art Club in 1886, but had little to do with its more progressive members such as Sickert and Steer. In the 1890s, he became a member of the Royal Society of British Artists (1894) and through his friendship with Edgar Wood was much involved in the Arts and Crafts Movement.