James Watterston Herald's only formal art training was at Herkomer's School in Bushey.
In the 1890s he lived in Croydon where he had success selling his work. In 1901 he returned to Arbroath.
James Watterston Herald worked mainly in watercolour and pastel. His technique is in the manner of Arthur Melville. He liked to paint town scenes often with figures on wet pavements. He died at 55 from cirrhosis of the liver.