Toronto’s oldest hotels and the secrets behind their iconic bars

Toronto’s oldest hotel bars are sharing their century-old secrets so you can maximize pulling up a bar stool without booking a room. 

This city is old, and as a result, lavish institutions sprang up in the early days of urbanization, all wanting to provide only the plumpest of chequebooks with the most pampering possible. 

Glamour and opulence haven’t left Toronto in the centuries since; in fact, they remain major social and cultural engines today. However, today, the oldest players in the hotel scene want to make the hotel bar accessible, and not just for the highest bidder. 

The Broadview (Rooftop Bar)

Whether you are burning time on a two-hour-long line for an Ossington ice cream cone or trying to jimmy a reservation at a College St. restaurant, if you have walking-around money, west Toronto will eat it up in an afternoon. 

However, just an inch east of the DVP is Riverside, a neighbourhood that harbours The Broadview, a 135-year-old building made of pure brick and class.

While numerous bars, lounges, and restaurants have rotated out of The Broadview in its history, as it has gone from commercial dwellings to a hotel, to a boarding house with a *cough* certain club on its main floor, to a luxury hotel again, the place has never lost a hint of its charm. 

In fact, the east end has become a hotbed for what many in Toronto agree is a place for cool parents to raise cool kids in a cool neighbourhood that maybe won’t price you out.

As a result, the Broadview has almost retroactively become a locale of a similar vibe. 

Details on its new ground-floor pub, Archie’s (named for the building’s founder), can be found here. However, it’s the iconic rooftop bar that will be the main star of this story. 

[A view from the top at The Broadview]

“I mean, the whole building was built in 1891, and to this day, it functions as a beacon of the east end, and when we speak to a lot of our guests, especially those having a staycation, it’s often their first time coming this far out east. It’s a community hub, and that’s what this building was envisioned as even before the first brick was laid,” Jason Chapman, The Broadview’s food and beverage director, told yourcitywithIN. 

Chapman went on to note, as a Scarborough native, the definition of what ‘east’ is is subject to change; for him, growing up, Riverside and Leslieville were considered as downtown as it gets, with further west being an entirely different world with different people.  

To an extent, Chapman believes that remains the case, with the west side remaining so noisy for attention, condos, and more; a stroll eastward for some becomes an odyssey unto itself. 

What The Broadview and its programming want to do is give Torontonians a touchstone for the east end, as even the hotel itself is a gateway to the bounty of neighbourhoods on that side of town. 

[The glitz and glamour of the rooftop bar at The Broadview]

“The rooftop is where you are going to see the most eclectic and diverse range of people, whether guests or neighbourhood regulars. It has, in its own way, become a destination spot; we have repeat clientele from all over the world, and all over the city, which further supports that magic of a hotel bar,” says Chapman.

So what makes Toronto’s old hotels, and the bars/restaraunts within them, so special? Well, according to their proprietors, while most places competing for recreational savings offer a barrage of ‘elevated takes on classics,’ the hotel bar stays just that — classic. 

“When you think about it, we don’t want there to be a specific reason for you to swing by,” says William Hillario, senior food and beverage manager at The Broadview. “We can cater to any sort of situation, because our programming is just that malleable; we put a lot of consideration into both the quality and how quickly we can churn out only the best when made to order.”

This throughline is in the very marrow of a good hotel bar, as set menus, often built around one vision, make it enjoyed by those who need consistency — with a side of new faces every visit. 

[While the patio is nice, the rooftop bar at The Broadview has views of the city year-round]

What The Broadview has going for it to complement the classic essence of a hotel bar is its view; as compared to the towering spires of the west end, the rooftop bar here offers a view looking west that is hard to find, or beat, anywhere else in the city. 

Coupled with the right stiff drink and good company, whether those getting off a plane or your next-door neighbour, The Broadview’s rooftop bar is perfect for a little bit of perspective, and just the right amount of indulgence. 

The Gladstone (Cassette)

You got your Presto card? Good. Because we’re hopping on the 501 and taking it all the way to The Gladstone House on Queen West. 

Built in 1889, unlike its eastside contemporary, The Gladstone was purpose-built as a hotel for those cruising into Toronto on the Canadian Pacific Railway — and as most now know, travelling makes for thirsty work. 

While its adjoining bar has had numerous names (and vibes), last year, the powers-that-be behind The Gladstone introduced Casette, a retro-style bar built on classic cocktails and small bites. 

Operating amid the noise of West Toronto, The Gladstone and Cassette hunker down in the heart of the action, paying homage to their days accommodating dusty travellers; everything here is ground level and right in the middle of it all. 

[The lobby-side entrance to Cassette in The Gladstone]

“The Gladstone has always been really connected to the community in this end of town, and as a result, it became a huge hub for artists and other creatives to meet up and connect — it has so much character in its walls as a result of that,” Laura Squires, general manager of The Gladstone House, told yourcitywithIN. 

Squires has a rather deep connection to this corner hotel, as her great-grandfather used to be a night manager for The Gladstone.

“We have so many areas dotted around where there are photos and little artifacts of the original restaurant that opened with the hotel, which are foundational pillars of how we operate here,” says Squires. 

The previous incarnation of the adjoining hotel haunt was the Melody Bar, a sprawling space built around big shows and big nights, which had a 20-year tenure operating on that corner. 

However, like many locations in the early 2020s, it closed and was only recently resurrected as Cassette. 

[Retro lighting and retro style, done earnestly at Cassette]

“We wanted to still keep a piece of that history and identity alive, but at the same time, we have to make a throughline to what trends and community needs are currently in Toronto now. So, as a result, sticking to the classic hotel bar feel and making it energetic and social was a priority,” says Squires. 

Retro decor dominates Cassette, while an intimate piano corner evokes the old-school lounge feel one would expect from such a space. 

Complimented by the muffled noise of Queen West on a busy night, plus the ‘ca-chunk’ of the streetcar going by, Cassette perfectly functions as a living homage to The Gladstone’s past, while ensuring the crowds of tomorrow are wine’d and dine’d. 

[Grab a drink and do some people watching at Cassette]

Part of this hospitality was a focus on the fact that the neighbourhood is designed to appeal to crowds, further bolstering what any hotel bar wants to do, which is draw in more people from outside the hotel. 

“They’re out there in the neighbourhood, and they love to come out; we have even kind of made some off-the-cuff karaoke programming, and people just love to come in and sing. People often just want to come in and experience a good bar, no strings, few gimmicks, and we had the environment to make that a huge part of our programming,” says Squires. 

The Gladstone’s is steeped in history and is further complemented by the fact that just behind a door to the right of the lobby is a space designed to accommodate all tastes. 

The Fairmont Royal York (The Library Bar) 

Here we are, the big one, the absolute crown jewel of Toronto’s oldest hotels, The Fairmont Royal York.

This sprawling gilded hotel,  just shy of its 100th anniversary, much like The Gladstone, was designed as a beacon for those coming into town via Canada’s then-sprawling railway system. 

Due to its substantial size, The Fairmont Royal York hosts three iconic restaurant and cocktail venues. But if there is one that is as iconic as the towering structure of the Royal York itself, it’s the Library Bar.

“This building, and by extension us, are the first thing a lot of people see, because naturally, we are right across the street from Union Station, so whether coming in by train from the airport or elsewhere, we are the first thing seen — we are in essence that way, ambassadors to the city,” James Grant, director of food and beverage for The Fairmont Royal York, told yourcitywithIN. 

[Opulence and more hidden inside the Fairmont Royal York]

As a result, the main lobby has its own lounge bar in the form of Clockwork, which is only a taste of what the hotel has to offer in terms of hospitality. It isn’t until you bank the corner to the Library Bar that the definitive experience takes place. 

Paying homage to its name, the Library Bar currently offers a menu curated around famous novels and authors who came from Toronto, supplying guests with a literary experience they get to taste, as opposed to read. 

“We wanted the team to take that idea, to take their favourite books with roots here, and to run with it,” says Grant.

With this hotel, and its adjoining bar being by far the largest in this collection, Grant was quick to note that not overwhelming guests was a crucial part of the experience, as above all else, a hotel bar should soothe the weary. 

As a result, the Library Bar has a few standbys that guests can indulge in, with the famous Birdbath Martini, which is made to order with either their Quill Gin or Quill Vodka.

[As good as it gets at the Fairmont Royal York’s Library Bar]

“In one way or another, this has been on the menu ever since this bar opened. When I came on board, I simply directed that it needs to be, in essence, ‘the perfect martini.’ It doesn’t matter how you normally drink yours; when you come in here and get this, the only words coming out of your mouth are, ‘god damn, this is a great martini,’ says Grant. 

Grant further stated that while martinis are usually only three components, it still took him and his team six months to get it exactly where it needed to be. 

[Bottle service anyone?]

As for what makes a hotel bar magical, Grant had immense insight, not only in celebrating their history, but also in highlighting that they function as a social space many in Toronto are looking for, but often discredit. 

“Hotel bars are that missing ‘third space’ many people in this city are looking for. The number of times I have walked into a hotel bar and seen strangers sitting and mingling meaningfully is too many times to count. They’re trapped in time that way — they are an oasis away from the chaos of the world.”