"Beats all creation, the new CPR Station", asserted the huge posters that hung on the newly completed Windsor Street Station. CPR president, William Van Horne's own words were used to announce the grand opening.

Bruce Price, the New York architect, who had recently completed the company's spectacular Banff Springs Hotel in the Rocky Mountains of Alberta, had been chosen to design the station. Van Horne, however, proved to be a difficult client to please and Price was forced to submit several designs. The "Richardsonian" style eventually chosen was built between June 1887 and February 1889, at a cost of $300,000. The CPR's new Montreal headquarters consisted of a freight depot, passenger terminus, an elaborately vaulted waiting room, a ladies waiting room, tub and shower facilities and a barbershop. Dining rooms were provided for in the basement.

By the turn of the century, the company had outgrown the building and Montreal architect, Edward Maxwell, was commissioned to design an extension to the west of the original building along Osborne Street (now de la Gauchetière). Built between 1900 and 1906, the Maxwell wing was constructed on a steel skeleton instead of the wall-bearing construction used in the Price building. Maxwell's design went to great lengths to complement the original structure. The central feature of Maxwell's work was an elegant five-arch open carriageway to accept the burgeoning passenger traffic.

In 1906, W.S. Painter, who had been appointed "Architect for the Company", designed an economical building to house the Dominion Express Company, a CPR subsidiary. The no-nonsense building continued once again along Osborne Street. The drab two-and-a-half storey reinforced concrete structure broke from the Station's classic image and was soon dubbed "the mud hut" by disapproving employees. After several uninspiring renovations, the majority of the "mud hut" was eventually demolished in 1973.

In 1909, when the Company had once again outgrown its Windsor Street offices, Painter was given an opportunity to design yet another much grander addition. This time, the extension ran down Windsor Street (now Peel) and more than doubled the size of the existing station. At the time of its completion in 1914, the impressive 15-storey tower was the highest commercial landmark on Montreal's skyline and the spectacular steel-arches in the passenger concourse supported the largest glass-roof structure in Canada. The Painter wing also incorporated a sturdy new train shed. The "Bush" sheds, as they were named, after the engineer who designed the system, alternated skylit passenger and baggage platforms between the tracks with open slots that allowed engine smoke to escape. Rows of steel columns and arched trusses supported the train shed. Below the rows of tracks, enormous, cavernous vaults were created in the process. Except for the modest example left to demonstrate the 19th-century style of architecture, the sheds were demolished to eventually make way for a landscaped courtyard and the adjacent Molson Centre, home to the Montreal Canadiens.

Canada and CPR saw enormous amounts of growth during the early 20th-century and Windsor Station's concourse witnessed the comings and goings of thousands of passengers - men and women off to build new futures and to fight wars. In 1922, CPR commissioned Canadian sculptor Coeur-de-Lion MacCarthy to create a statue to commemorate the employees who sacrificed their lives during First World War. The concourse continues to be home for the imposing "Winged Victory" statue that was later dedicated to the employees of both World Wars.

In 1954, the last major addition to Windsor Station was completed with the construction of a contemporary-styled structure, along St. Antoine Street, intended to house the Company's accounting departments. The building's claim to fame was not on the architectural front, but rather on the technological, with the installation of the first IBM 750 computer in Canada.

In 1978, the Company began an ambitious eight-year renovation project that included new copper and slate roofs, hydraulic elevators, air conditioning throughout, fire and security alarms and the replacement of 1,785 double-glazed windows. The entire limestone façade was also repaired and cleaned, washing away decades of soot and pollution.

In 1983, the "Ordre des architectes du Québec" honored the Company's efforts towards the conservation and preservation of architecturally significant structures by awarding it the prestigious << Prix Thomas Baillargé >>. In 1990, Windsor Station was named the first heritage railway station in Canada, the very first day a law was enacted, to recognize and protect railway stations. In 1997, Canadian Pacific in conjunction with the Molson Companies undertook a major real estate and revitalization project that included the construction of the adjoining Molson Centre. In February 1999, Historic Sites and Monuments Board of Canada recognized the national significance of the railway porters and their unions, by unveiling a plaque in the concourse of Windsor Station. The plaque can be found at the Peel and St. Antoine Streets entrance.

Although the Company's headquarters are now in Calgary, Alberta, Windsor Station continues to play a vital role as Montreal's "grande dame", housing a significant number of CPR employees, and the Canadian Pacific Railway Archives. The beautifully preserved concourse, one of the few large-scale facilities in Montreal, plays host to major events. The railway terminus, now located west of the Molson Centre, serves commuters only.