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It would be a mistake to believe that Sir William simply parked himself at Minister's Island for the summer and watched the clouds go by. He was nothing if not a workaholic. At the height of his career he is thought to have sat on the boards of about 40 companies, while running the operations of the CPR and building a railroad in Cuba. He was often in the West on tours of inspection. At other times he was in England or other parts of the world. In short, he was an extremely busy man and often found only brief intervals in which to enjoy himself at Minister's Island.While he might be there for a few weeks, he was often there for only a few days, and sometimes for only a few hours.
With a mobile and well-equipped office located in his private railroad car, on the other hand, it was easy to work all the way down from Montreal and back. In a certain sense, stepping out of his car at the Bar Road crossing was not much more time consuming than stepping out of his office at Windsor Station. Van Horne once made a curious statement to the London press in which he said that while on Minister's Island "I do no business." That certainly was not true. In 1896 for example he was visited by New Brunswick railroad baron Alexander "Boss" Gibson, who wanted to sell Sir William a railroad line in the northern part of the Province. It is difficult to believe that the visit of a Mr. Meysenburg, one of the iron kings of Pennsylvania, in the summer of 1896, was purely a pleasure trip.
Similarly with the visit in 1899 of a certain General Thomas, an industrialist interested in railways in both the United States and Canada. During the construction of the Cuba Railway individuals from that country were noted to be visiting Covenhoven. Businessmen interested, like Van Horne, in a power generation plant at Grand Falls, New Brunswick, were guests at Covenhoven in 1910. James Dunn, later President of Algoma Steel, a company that made its millions supplying rails to the CPR, was at Covenhoven in the summer of 1912, along with several British millionaires, in what may have been his first visit to the town.
When, in between guests and business, Sir William did have a little time to himself, he seems still to have kept busy. The roving Editor of the Beacon, whose many interviews with Sir William gave him an unusually complex appreciation of the man, remembered him on some of those occasions with a knockabout hat on his head, hands folded placidly over his ample belly, and a large cigar rolling in his mouth, but also as one who did not find repose in idly sleeping the moments away, but in superintending his farm, collecting and classifying fungi, arranging his flower beds and walks—and of course painting. In the summer of 1901 he was observed to have several newly completed canvases at his summer home. One depicted a scene he had observed on the Island a few weeks previously. While strolling on the beach he suddenly came in view of two handsome moose cooling their limbs in the water. Impressed with this scene, he immediately committed it to canvas. The work of that summer also included a storm at sea entitled "Sea Study," sketched while returning from Cuba. Another, "At the Foothills of the Rockies," showed a broad prairie in the foreground with Indians on horseback and a trail disappearing into the dim foothills ahead. It was Sir William's wont to present any of his friends who had moved to St. Andrews with a painting of his favorite subject—the birch trees on his Island. One such, the gift of summer resident Evan Gill to the town, now hangs in the St. Andrews public library.