In 1793, Governor John Graves Simcoe came across what would be the future site of Holland Landing, then known as St. Albans, and considered this area would make an ideal shipping and defense point between York (now Toronto) and Georgian Bay. Holland Landing was named after Samuel Holland, first Surveyor-General of British North America.

During the War of 1812, when the British decided to retake the entire lake Simcoe system through the construction of a number of first-rate ships in Kingston and Penetanguishene. A large anchor, over fifteen feet (roughly 4.6 m) long and weighing approximately 4000 lbs (about 1 816 kg), for the frigate under construction at Penetanguishene was shipped from England and had made it as far as Holland Landing when the war ended.

The idea for a canal combining to Lake Simcoe and the Trent-Severn Waterway was approved and construction started in 1906. Holland Landing would conjoin Newmarket and Bradford. It was almost complete in the summer of 1912 – three lift locks, three swing bridges and a turning basin – when the new government of Robert Borden cancelled the project. The project was discarded, earning it the name "The Ghost Canal". It continues to serve as a historical landmark.