[3] After an economic crisis in the mid-1820s crippled England, James became convinced that the family should emigrate to the colonies in Australia where their considerable wealth would allow them to receive large grants of land and put them into the first rank of society.

[3] The Hentys had hoped to obtain an order to select 80,000 acres (32,000 ha) upon arrival at the Swan River and hence quickly organised their transport to Australia.

The ship Caroline was chartered and James aided by his teenage brothers Stephen and John, was chosen to oversee the Henty family's colonial project.

They arrived at Fremantle in November 1829, with James being initially disappointed with the poor quality of the soil and the small 2,000 acre Stoke Farm land grant given to him.

James convinced Governor Stirling to give him an additional town allotment near Fremantle and also a large grant of land to the south, inland from the Leschenault Estuary, in a region which became known as the Henty Plains.

[3] Many of James' merino sheep at Stoke Farm died, his attempts at growing crops failed, and conflict between the Aborigines and the British in the area was increasing.

James realised that the attempts to establish themselves as graziers in the colony had failed, and decided to relocate to Van Diemen's Land where he would invest the family capital into the creation of a merchant business.

James' brothers Edward and Stephen on their voyages along the southern coast of Australia, saw an opportunity to set up a sheep station at the whaling outpost of Portland Bay.

Their father, Thomas was impressed with the land when he visited and sent James to England in 1834 to negotiate with the royal government a grant of 20,000 acres on this uncolonised part of the southern coast of Australia.

[3][4] James returned to Launceston in October 1835 to find that Edward and Stephen had already gone to Portland Bay to establish a farm and whaling station without waiting for the permission of the British government.