About Jackson's Landing
The Roaring Twenties…Living the good life at Jackson’s Landing
By 1927, the remains of the Enterprise were lying at the bottom of the lake and the marine railway was no longer in use (although it remained intact and is still visible on calm days). The property at the tip of the Point was sold that year to Irving Robertson, a wealthy and powerful newspaperman as the site for his spectacular summer home. The son of newspaper tycoon and philanthropist John Ross Robertson, Irving had established his own career as Editor in Chief of the Evening Telegram, one of the largest newspapers in Canada, as well as Chairman of the Hospital for Sick Children in Toronto. His academic credentials included Upper Canada College and Oxford University.
For all his wealth, power and prestige however, Irving Robertson was not a happy man. His mother had died when he was only four years old and his father had married, according to a biographer, “a woman of steely principles, dogmatic and determined” and her relationship with Irving was never warm or motherly.

Jackson's Point Hotel
For his part, Irving became well known as a “bon vivant” much to his stepmother’s disapproval. When he finally decided to marry at the age of 45, he proposed to his nurse, who was caring for him through ailments aggravated by his heavy drinking. They married in Sutton in the fall of 1927 and he acquired the Point for his bride as a wedding present, a place to make a fresh start. The summer resort cottages were removed, stone masons were brought in from Scotland and by the end of 1928 the summer residence was completed.
At this spacious summer home with a great lawn studded with fruit trees sloping down to the lake, the Robertson’s entertained the Canadian and international social elite and it was here that Robertson was most happy. His time was running out, however, and the heavy drinking was taking its toll despite the best efforts of his teatotalling wife. In the late fall of 1931 he slipped into a coma brought on by cirrhosis of the liver and he died soon after the New Year of 1932. The newspapers were full of stories about Robertson and the rival Globe newspaper reported on “the long funeral procession – one of the most impressive ever witnessed on Toronto streets”.

Cutting ice on Lake Simcoe
Modern Note: We have found the evidence of Irving Robertson’s life here in some intriguing ways. During the extensive renovation of 2003/2004 we became curious about an area of the basement which was completely enclosed by thick concrete walls with only a small opening of a few inches near the top of one wall making it impossible to see inside. Finally giving in to our curiosity we brought in a crew of concrete cutters to open a section of the wall, more than a foot of solid concrete. Inside, with the section removed we found the evidence that had been hidden there since Robertson’s death – hundreds of empty whisky bottles with excise labels from 1928 – 1931 which he had hidden there, away from his disapproving wife.
Reservations: Call 1-905-722-7752 or email info@jacksonslandingbb.com