In 1819, he joined a friend who was sailing to North America. After four weeks they landed in Halifax, Nova Scotia, where Bennett briefly worked as a schoolmaster till he had enough money to sail south to Portland, Maine, where he again taught school in the village of Addison, moving on to Boston, Massachusetts by New Year's Day, 1820. He worked in New England as a proofreader and bookseller before the Charleston Courier in Charleston, South Carolina hired him to translate Spanish language news reports, so he briefly relocated to The South. He moved back north to New York City in 1823, where he worked first as a freelance paper Writer and, then, assistant Editor of the New York Courier and Enquirer, one of the oldest newspapers in the city.