In 1829, a James WEBSTER had a business on Highgate, Kendal as a tailor and woollen draper. It may have been James that matched up his youngest sister Hannah WEBSTER with another tailor, Thomas SCOTT. An account of one of his customers indicates that he was still in business in April 1847.
Additionally, a James WEBSTER was proprietor of the Commercial Hotel aka Commercial Inn (and Posting House) on Highgate in 1809 and 1835.