He settled down to the congenial occupation of stockbreeding, on what was then considered to be a large scale.

Finding that his stock did not thrive so well in the immediate neighbourhood of the sea coast, and wanting more land for pasturing his increasing herds, he made anxious enquiries in all directions as to the possibility of crossing the Blue Mountains inland.
Nobody would entertain such a suggestion, the failures had been too many: every one to whom he broached the subject declared it to be impossible, prophesying that the extension of the settlement westward would forever be obstructed by their unscalable heights.

Blaxland, however, was not intimidated by these disheartening predictions; and, in 1811, he started out on a short journey of investigation, in company with three Europeans and two natives.

On this trip he found that by keeping on the crowning ridge or dividing water-shed between the streams running into the Nepean and those that fed what he then took to be an inland river, he got along fairly well.

Some time afterwards he accompanied the Governor in a boat excursion up the Warragamba, a tributary of the Nepean, and though there were no noteworthy results, it convinced Blaxland that, could he follow his former tactics of adhering to the leading ridge that formed the divide between the tributaries of the northern bank of this river and the affluents of the Grose, a tributary of the Hawkesbury, he would attain his object and reach the highlands.