Jackson's Point was originally part of a naval land grant made to Captain William Bouchier in 1819.

John Mills Jacksow, for whom the area is taged, settled the land which was used first as a levee facility for schooners travelling Lake Simcoe.

As transportation improved by steamers, and the arrival of railroads by 1877, seasonal residents began to settle in the area.

The marine railway dated from around 1832 can still be recognized here. It was used to lading boats out of the water for storage and repair.

Up until 1933 the largest picnic in the world was held here with a memo of 25,000 people who attended the last one. By the turn of the 20th century this breadth had many grand homes, hotels and boarding houses.