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By the fall of 1901 Van Horne was fed up with the small size of his cottage. Wanting something bigger and bulgier, he and Edward Maxwell collaborated on an addition to the rear or north end of the house which would double its size. By the spring of 1902 the finished product showed what has become the classic Covenhoven. There was another addition in the form of a porte-cochère, an extension of the verandah, carried out 40 feet over the driveway, roofed over, and supported on either side with sandstone pillars. The driveway was carried several hundred feet beyond this structure, and ended in a circle of flowers. Finally, a rustic cottage with a thatched roof was built at the south-east end of the Island. This was in all probability what was known to the Van Hornes as "Belvedere," a favorite bathing spot for daughter Adaline and sister Mary.There were two more notable additions to Covenhoven in Van Horne's lifetime. The smaller was a new studio, which was constructed outdoors on the east side of Covenhoven in 1909. The larger was a new wing added to the eastern side of the building in 1910. It was 40 x 45 feet in size, comprising a wine cellar in the basement, space for the enlargement of the music room, a large studio for Sir William and a billiard room. On the second floor were two large bedrooms to be used by Benny and his wife. On the floor above was room for another bedroom or two, with an observatory to command a wide sweep of the bay and islands.
The next year Van Horne finished off the interiors of these two new additions. CPR Chief Architect Walter Painter was put in charge of the business, which included marble-topped radiators to match those in the rest of the house, bookcases and a combination billiard / pool table for the annex.
In the fall of 1911 and through the spring of 1912, the picturesque circular bathhouse tower was added to the property at the southern tip of the Island, where it commanded a panoramic view of the Bay. On this project Painter collaborated with London architect Francis Swales, who seems to have been chiefly in charge of the tower's design and details. The red limestone was blasted out of the beach nearby, and the stones laid by local masons Charles Horsnell and Joseph Gibson. The blocks were left in a rough state, with drill holes showing, to economize on labour or, what is more likely, to create a more rustic effect. The upper floor featured 360 degrees of open windows and a drain hole in the floor to let out the rain, changing rooms on the lower floor, and beneath this a curving walkway which led to a salt-water pool. The pool was 4 feet deep at low tide, 8 feet at high, had a drain to let out warm water, and at least once acted as an impromptu weir. One morning it was found filled with a school of silver hake which had gotten trapped at low tide, smothered, and had to be shovelled out.
By this time, Covenhoven was an unmodestly spectacular summer cottage. There were about 28 rooms in all, not counting closets and utility rooms. The centerpiece of the downstairs was the drawing room, 40 x 26 feet in size, with large double doors opening onto the verandah, from which opened the long vista of Passamaquoddy Bay south to Eastport. On the opposite wall stood the massive sandstone fireplace, flanked by carved floor-to-ceiling columns of grape vines inlaid with gold leaf. These columns have been attributed to renowned American architect Stanford White. According to an article by W. A. Craick which appeared in MacLean's Magazine in 1912, if one were set down in this room "without being aware of one's whereabouts, the first thought would be that one was in the midst of some great city. To conceive of such surroundings in a summer residence many miles from any city," wrote Craick, "would be almost impossible."
To the right of the drawing room, located in the annex of 1910, was the long, narrow2 music hall, 30 x 11 feet, with Sir William's spacious studio and bedroom, each roughly 20 feet square, adjacent to that. To the other side was the flower room, and straight ahead were the 30 x 24 foot dining room and 20 x 16 foot card room. The kitchen and laundry were also contained in the annex, as well as bedrooms for the butler and cook. All of the rooms in the lower section had 12 foot ceilings. Upstairs, in rooms about 9 feet in height, were about 9 bedrooms, 3 of which were large suites, about 24 feet square—one for Mrs. Van Horne, one for Adaline and one for Benny, as well as various other, slightly smaller bedrooms and bathrooms for guests. Sir William's grandson, William Cornelius Covenhoven, Jr., born in 1907, had his own nurse, and the nurse her quarters adjacent to his bedroom. There were also a sewing room and large storeroom on this floor.
The furnishings of the house tended toward the massive, like Sir William. In its heyday, the long drawing room table was set with heavy, carved mahogany chairs, underneath which stretched a Persian carpet large enough to require 6 staff to drag it out for spring cleaning. Along one wall was a goodly length of bookshelves, with hundreds of volumes generally encyclopaedic in nature, on subjects ranging from art to fungi to train operation. The single most spectacular item of furniture was the hand-carved 17th-century Spanish cabinet in which Van Horne kept his painting supplies. The CPR, with its steamer service on the Pacific, had opened up the Orient to the West, and Chinese and Japanese pottery had become fashionable in Canada. Sir William had become a Canadian authority on this subject as well as a notable collector of it. The wall cases in his drawing rooms at both Sherbrooke Street and at Covenhoven displayed many vases, tea bowls, bottles, jars and bowls from the East, some priceless. He was an avid art collector, too, and his collection included masterpieces. Covenhoven would probably not have displayed his most highly prized paintings, such as his Murillo, which he purchased in 1911 for $25,000, or his Rembrandts. These would have been kept safe in his Montreal home, but at Covenhoven at its high point there would probably have been at least a hundred paintings adorning its various walls. The assortment was eclectic, but Canada was well represented, and included friends such as John Hammond, William Hope and Edward Colonna. Many were his own compositions. Sometimes as a joke on the overly credulous he liked to pass off his own works as European masterpieces.