Hotels with History
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Hotels with History

Five stunning hotels that will give visitors to Toronto a glimpse into the past.

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Toronto, like so many big cities that came of age in the mid 20th century, spent a lot of time and effort bulldozing its architectural heritage to make way for more modern but often less interesting structures. Fortunately, however, some buildings do remain to provide a bit of historical perspective to locals and visitors alike. Among the most prominent? A handful of century-old hotels. Staying a night or two at these notable accommodations is a surefire way to get an up-close view of Toronto’s past—while, yes, enjoying today’s creature comforts. We teamed up with to bring you five hotels that will give you a glimpse into the Toronto of yesteryear.

Fairmont Royal York
Though gargantuan office towers and condos now surround it, the Royal York was for decades one of the defining features of Toronto’s skyline. When it opened in 1929, as part of a network of Canadian Pacific Railway hotels (like the similarly styled Chateau Frontenac in Quebec City and Chateau Laurier in Ottawa), the Royal York stood as the largest building in the British Commonwealth. It was also among the most popular: Its late Imperial Room nightclub hosted performers from Tony Bennett to Tina Turner, and the hotel has served as residence to Queen Elizabeth II and other Royal Family members during their visits Toronto.

While numerous heritage features remain—check out the lobby’s ornate adornments, for example—the passing years have also brought many changes. A garden and apiary are now found on the rooftop terrace; they supply herbs, produce and honey to the Royal York’s lauded restaurants. And the hotel just underwent a five-year revitalization that included the complete renovation of nearly 900 guestrooms and updates to its health club.

Omni King Edward Hotel
King Edward VII isn’t the only big name associated with this hotel’s history. It was co-designed by E.J. Lennox, architect of Toronto’s Old City Hall and Casa Loma (among other notable buildings) at the behest of George Gooderham, a prominent developer and son of William Gooderham—yes, of the Gooderham and Worts Distillery. The accommodations are every bit as opulent as they were when they opened in 1903. A recent $40-million renovation brought updates to most guestrooms and common areas, and allowed for the reopening of the hotel’s long-shuttered 17th-floor Crystal Ballroom, which is now a supremely elegant wedding venue.

Of course, the King Eddy is still a place to rub shoulders with higher fliers: Brunch or high tea in Victoria’s Restaurant are very popular, while the swanky Consort Bar offers great people watching. And guests in the hotel’s 29 new Royal Club rooms can hobnob in an exclusive lounge, which offers a daily breakfast, complimentary beverages during cocktail hours, evening hor d’oeuvres and more.

The Drake Hotel
It’s hard to believe that barely more than a decade has passed since this relatively nondescript building was transformed from a derelict rave den into Toronto’s quintessential boutique hotel and the locus of a community’s cultural and economic renaissance. Erected in 1890, the building’s fate has since followed the ups and downs of its West Queen West home. Its initial use was as accommodations for visitors to what was then a wealthy area; it became a flophouse during the neighbourhood’s midcentury decline. But since 2004 its 19 rooms, all uniquely decorated with contemporary art, high-end finishes and numerous quirky touches have hosted hip travellers looking to be in the thick of Toronto’s sceneiest of scenes. The hotel is a major hub during glam events like the Toronto International Film Festival, and its popular restaurant, rooftop lounge and subterranean concert stage are see-and-be-seen spots year-round. Return in a year or two to check out the Drake’s expansion: Two adjacent buildings are being refurbished and enlarged to accommodate additional 30 or so rooms.

The Windsor Arms
Like the Drake, the Windsor Arms enjoyed a storied early history (built in 1927, the four-storey, neo gothic inn was designed to complement the striking Victorian structures of the nearby University of Toronto), but fell into disrepair in the latter half of the 20th century. Notably, the founders of TIFF used the Windsor Arms as their headquarters during the inaugural 1976 festival, but the hotel was derelict by the late ‘80s. A small handful of original elements were preserved as part of its 1999 rebuild, including the fireplace and stained glass windows in the tea room—which has itself become something of a Toronto institution for, well, traditional afternoon tea service. Classicist leanings pervade the hotel’s 28 suites, too: Expect plush furnishings, stately bureaus and, in one room, a playable harp.

The Old Mill
Built in 1914 as a restaurant sited next to the ruins of an old gristmill in Toronto’s west end, the Old Mill subsequently saw a number of additions—including a banquet hall and wedding chapel—such that the Tudor-style structure became something of a community centre. In fact, it was only in 2001 that the restored site became a proper inn, featuring 57 rooms and suites, as well as a posh spa and intimate bar with live jazz and a respectable scotch selection. One thing hasn’t changed, though: It’s still a very popular spot for tying the knot.


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