Born in Forfar, Herald was a house painter and clerk in a textile mill. He then moved with his family to Edinburgh in 1884. He studied art in Dundee, Edinburgh and later at Herkomer's School in Bushey, where he shared a house with Nicholson and Hyde. He often painted townscapes, employing an imaginative colour palette, often unrelated to nature. The influence of Arthur Melville is clear in his work. His works have a poetic quality which, had he not been such a recluse, might have brought wider acclaim during his lifetime. After a period living in Croydon in the 1890s, he returned to Arbroath in 1901. He worked in watercolour and pastel, and, under the influence of Melville practised the 'blotesque' technique. He mainly chose harbour scenes as the focus of his watercolours, Arbroath, Auchmuthie and Hastings being the main locations. Many of these were scenes at dusk or painted during or just after rain to show the reflections on the streets and pavements. His pastels, however, tended to depict pastoral scenes, with cattle or figures in fields or orchards.