Ten days after arriving in Nova Scotia in 1783, Wentworth was off making his rounds. That autumn the 46-year old Wentworth was tramping the woods with his assistants, going as far as Annapolis Royal. He not only looked at standing timber, but that which had been felled. Sawmills were always to be a favourite object of his attention. The territory for which Wentworth was responsible was very wide. Nova Scotia then included the current day Canadian province of New Brunswick, and interestingly part of the current day State of Maine.

Wentworth received a 800 pounds, annually for his office as surveyor general. He had requested half as much again so that he could pay the expenses of his offices, but was generally denied. Thus it was that Wentworth supplemented things by taking fees whenever he approved a grant of land. Governor Parr took issue on the basis that the people he was taking fees from (newly arrived loyalists) were promised land grants without fees. Wentworth was to receive orders directly from London to stop taking fees. This development made things that much more difficult for the Wentworth household at Halifax. During the years between his governorships, and likely throughout his life, he suffered from a lack of funds, as so many of the crown office-holders did. It was not so much that such people did not receive a fairly handsome yearly salary from the crown, it's just that they felt obliged to spend beyond their means to maintain a lifestyle which they believed was connected to the office they held.