Berry is fascinated by history. Much of his inspiration is drawn from visiting places and encountering pieces of their histories, provoking for Berry what he describes as an "awareness that much has happened here in the past - great tectonic upheavals, life growing from the ooze, evolution, human history, many many footprints left under the surface, scents left hanging in the breeze". In 2002, while in residency in Southland, he discovered the diary of a surveyor in the Fiordland expedition of 1926-7 and drew on it to produce a body of paintings resonant with New Zealand's colonial and pre-colonial history, geology, mapmaking and the history of exploration. His 2005 exhibition Unsettled Land continued to trace the histories and stories of places and of man's imprint on the land.

Berry's most recent work has focused on a more personal history, told through the multicoloured lens of childhood. In 2007 he produced an exhibition entitled The Road Home, a collection of childlike paintings that are innocent but not naive, populated by stickmen and brightly coloured trees and dominated by the recurring motif of roads, suggesting a different kind of journey.