In 1796 Wentworth arrived in Sydney. It was then a poor prison settlement. The family lived at Parramatta. His father became a prosperous landowner. In 1802 he was sent to England. He went to a school in London. He returned to Sydney in 1810. He was appointed acting Provost-Marshall by Governor Lachlan Macquarie. He was given a land grant of on the Nepean River.