Canadian Pacific initially received a land grant of 25 million acres (10 million hectares). Over the years it acquired assets in mining and smelting and in timber. In 1956 it set out to develop these assets, establishing subsidiaries in oil and gas, minerals, fertilizers, food products, forest products, real estate, hotels, finance, trucking, telecommunications, shipping lines, and airlines. These assets were centralized in a holding company, Canadian Pacific Investments Ltd., in 1962 (renamed Canadian Pacific Ltd. in 1971). Canadian Pacific's passenger services were taken over in 1978 by the crown corporation VIA Rail Canada (VIA Rail Canada, Inc.).

For much of the company's history, most of its owners lived outside Canada, but this began to change after World War II as more Canadians began to invest in the company. By the late 20th century, about two-thirds of the voting rights were held by Canadian investors.

In 1980 the company became Canadian Pacific Enterprises Ltd., whose subsidiaries included Canadian Pacific Hotels (merged with Fairmont Hotels in 1999), CP Ships, PanCanadian Energy, and Fording Coal. The parent company divested its remaining interests in 2001, with Canadian Pacific Railway being spun off as a separate business. At the beginning of the 21st century, the railroad's transcontinental network served ports in Montreal and Vancouver, and it extended into U.S. cities such as Chicago, Washington, D.C., Philadelphia, and Buffalo, New York. See also Canadian National Railway (Canadian National Railway Company).