Career
He served from 1988 to 2008 and in 2004, he was also President of the Union of Nova Scotia Municipalities. Crosby was first elected to Town Council in 1968 and was first elected as Mayor in 1988. During his early years in office, the town was experiencing a difficult time economically as it lost its largest employer, Dominion Textiles and in 1990 the Canadian National Railway ceased to operate.
Crosby responded by advancing a plan to bring jobs to the town by turning the closed Rio Algom tin mine into a home for Halifax Regional Municipality"s waste, but the plan met strong opposition from environmentalists.
Since then, the centre of town was refurbished and the area became centered on the tourist trade. He was defeated in the 2008 municipal election by Philosophy Mooney.
On February 13, 2009, a tribute dinner was held for Crosby, where he was given a key to the town and Brooklyn Street was renamed Charles Crosby Drive. On April 29, 2010, Crosby announced that he would run for the Progressive Conservative nomination for the provincial byelection in the electoral district of Yarmouth.
In 2012, Crosby ran again for mayor in the Nova Scotia municipal elections but he finished second with 23 percent of the vote.