In the history of Windsor, published in 1996, L.S. Loomer writes that there were accidents on the railway almost from the first day. In 1855, two years before the projected line from Halifax was supposed to reach Windsor, a locomotive named the Mayflower went off the track. The damage was minimal but it was the first recorded incident and one of many that would plague the railway as the line was extended to Windsor and west through the Annapolis Valley.

Some of the early accidents on the line, written about by Loomer, were fatal. Three, possibly four brakemen were killed in separate accidents, Loomer said, when their heads struck a footbridge the railway built over Wentworth Road in Windsor. The footbridge eventually was replaced by a standard crossing, but too late to save the lives of the brakemen.

Like Loomer, Marguerite Woodworth records various accidents in her history of the Dominion Atlantic Railway. All the incidents made the news, even the trivial accidents, and usually with plenty of detail by the newspapers of the day.