Nightlife Spots That Put the Word 'Entertain' in Toronto's Entertainment District

Toronto’s Entertainment District is a stretch of downtown, running roughly from Queen Street West on its northern edge and south to the lakeshore, with Spadina Avenue and University Avenue along its west and east borders. This is where the action is: the shopping, hotels, restaurants and theatres. During the week, it is filled with busy commuters who rush to work, coffee cups in hand, eyes downcast at cell phones.

There’s certainly plenty to see and do in the Entertainment District during the day, yet the excitement revs up when the sun goes down. For about 20 years, from the 1980s to the early 2000s, nightlife in the Entertainment District was centered primarily around the large dance clubs that opened in early 20th century warehouse spaces. The club crowd was a vibrant presence most nights of the week, bringing large numbers of young people into the area while also prompting older crowds to stay away.

A shift in thinking and city planning over the past decade has seen many of these clubs close. As condos sprouted as quickly as seedlings in spring, the number of Torontonians who live in the Entertainment District has substantially increased from just a few hundred to several thousand. The change has caused a growth in the nightlife options available. Where clubs were once dominant, you’ll now find sleek cocktail lounges and the perfect pub for an after-work pint. Today’s Entertainment District is no longer just welcoming to rowdy youth. It is for all ages – even rowdy middle ages – in need of a good time.


When it comes to Fynn's of Temple drinking policy, the short answer is that you should do it. Whether it is their highly recommended brunch with $4 Mimosas and Caesars or a hefty dose of beer every night of the week, Fynn's extends their Irish hospitality one pint at a time. With dark wood accents, it is the perfect place to nurse your winter sorrows. When buds come onto the trees, their large patio opens and fills with people who have jobs that allow them to drink their lunches. Every night of the week there is a new special, including free oyster Fridays and $5 burger Tuesdays. Live pub music is played every Wednesday for winter, spring and fall. In the summer, they just expect that you will go outside.

Recommended for Best of Toronto's Entertainment District because: Great beer and lots of smiling people can be found at Fynn's. We wonder if the two are related?

Courtney's expert tip: As you can imagine, St. Patrick's day is kind of a big deal here. It makes Ireland itself look a little tame.

Read more about Fynn's of Temple Bar →

Bar Hop
Photo courtesy of Bar Hop

You may be able to have too many shoes, but you can never have too many brew pubs (too much beer is another thing, but let's not bring the mood down). Toronto's Barhop doesn't require that you engage in a tour of the city. There is more than enough brewing goodness in one place. You can get a large format table bottle if you and your friends are the sharing types, or you can sample from their seasonal beer list. There is even a nice array of gluten free beers and ciders. The gastropub atmosphere means that you are not stuck with some greasy reheated fare, but rather hearty food that matches the fancy brews. Start with the garlic brown butter doughnuts and don't shy away from the breaded pickles. Breath mints might be a nice thing to pack along with your wallet.

Recommended for Best of Toronto's Entertainment District because: Beer enthusiasts need not have another reason to partake in a pint, but the Bar Hop will give it.

Courtney's expert tip: Don't give up your drinking on a Sunday. $5 craft beers on Sundays are the reason to keep the weekend going a little longer.

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Photo courtesy of Pai Toronto

As you walk into the basement of a nondescript brick building, you either think, "This is going to be good," or "This is going to be horrible." Luckily, Pai's humble abode caters to the former thought. There is usually a wait, but it is Toronto and the line does move fast thanks to the 80-seat capacity. Things get loud in here, with excited patrons, booming music and sizzling dishes making their way to new tables at breakneck speeds. Named after a spot in Northern Thailand, Pai specializes in family style dishes, divided into "Snacks and Starters" and "Mains." Add the papaya salad and the Thai omelette to your usual repertoire.

Recommended for Best of Toronto's Entertainment District because: Thai food and a communal atmosphere can make for a great, smack-in-the-city night out.

Courtney's expert tip: Mango sticky rice for dessert is a must.

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Steam Whistle Brewery makes a Canadian pilsner that they are rightfully proud of. This local beer maker is located right near the Roger's Centre and the CN Tower and it is a perfect stop on the Toronto tourism train. Their beer recipe has been exacted using European brewing standards, yet there is a lightheartedness to the company that is all Canadian. The four ingredients of hops, malted barley, spring water and yeast are balanced to perfection. They say that the fifth ingredient is the passion of their staff. There are always events going on, from art shows to lobster bakes. You can also privately rent out the space for tours or even your own (big fat beer) wedding.

Recommended for Best of Toronto's Entertainment District because: Take the decision of "What beer should I drink?" away. In Toronto, Steam Whistle is a must try.

Courtney's expert tip: Go on the tour, if only to enjoy a sample of their beer. It often ends up being a rowdy bunch of people. Afterwards, enjoy a doughy pretzel at the bar.

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From press conferences to large scale versions of game night, The Real Sports Bar doesn't pull any punches. It treats you, the sports fan, and your relationship with your team with the utmost respect. Right beside the Air Canada Centre, on game nights the Real Sports Bar can have upwards of 1,000 people watching with rapt attention. The screen is larger than most apartments in Toronto. A number of games are often on at once for those who wish there were more hours in the day...for watching sports. Don't worry about going to the washroom, because there are screens there too.

Recommended for Best of Toronto's Entertainment District because: You have your comfy chair at home for the ultimate viewing party. Real Sports Bar kicks that chair in the junk.

Courtney's expert tip: If you have been dragged here and don't fancy yourself a fan, not to worry, the food is definitely a step up from most sports bars. However, you will have to remember when to cease the conversation to allow for cries of delight or dismay.

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Photo courtesy of N'Awlins

Toronto's Entertainment District has changed frequently over the past decade or so as tastes and consumer demands shift. But N'Awlins has been a fixture in the neighbourhood. Its success can be traced to offering a nightly schedule of live entertainment that includes blues, jazz and other New Orleans-inspired music. No matter when you visit N'Awlins, you're guaranteed to hear some talented musicians. The venue also offers a pretty solid menu of Cajun-Creole inspired dishes, from Cajun calamari to fried alligator to seafood jambalaya. (Alligator comes as an appetizer, if you want to test the waters, so to speak.)

Recommended for Best of Toronto's Entertainment District because: The first sign that you are a tourist is if you pronounce New Orleans as N'awlins. Luckily, Toronto is a very friendly tourist hub.

Courtney's expert tip: Half price apps at the bar from 4pm to 8pm. Legally they can't call it "happy hour" but don't let that stop you from being happy.

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The Porch
Photo courtesy of Porch Toronto

As Toronto's downtown gets more and more crowded, there has been nostalgia towards the suburban life. Bars with patios that look like your uncle's backyard and even names that conjure up a lazy afternoon drinking lemonade. Take The Porch, for example. It is located just blocks from the Rogers Centre and offers unparalleled views of the city (which may be preferred to unparalleled views of your creepy neighbour). Margaritas (in mango, raspberry, strawberry and lime flavours), craft beers and drinks in a pail to share are all ways to cool off from the hot summer heat. It can get very busy after work hours, so if possible go during lunchtime to fully savour the experience.

Recommended for Best of Toronto's Entertainment District because: DJs, a Instagram worthy view and buckets of margaritas? Yes please.

Courtney's expert tip: If you like your eggs benny with one heck of a view, you have met your new favourite brunch spot.

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DEQ Terrace and Lounge
Photo courtesy of The Ritz Carlton

Wear something fancy and indulge in an equally fancy cocktail at the Ritz Carlton's elegant DEQ Terrace and Lounge. During the winter, cozy fireplaces and furnishings inspire patrons to hunker down. During the summer, the fireplace will follow you outside to the expansive patio which has one of the best views of CN Tower and downtown Toronto. Enjoy complimentary marinated olives and Maple Cajun toasted nuts while you imbibe, or indulge in a lovely light menu that includes gems like the astoundingly good fried chickpea fritters with carrot harissa, yogurt, cilantro and cashew. Cocktails are one-of-a-kind, with luxurious choices such as "The Goose In The Hurricane" with Grey Goose, Rum, Passion Fruit Puree and Grenadine.

Recommended for Best of Toronto's Entertainment District because: Deq is a great place to spend a night among stylish people, or to grab a drink before or after hitting the clubs.

Courtney's expert tip: Located across the street from Roy Thomson Hall, Deq is ideally located for those enjoying a Toronto Symphony Orchestra performance.

Read more about DEQ Terrace and Lounge →

SPIN Toronto
Photo courtesy of Caitlin Wickham

Ping pong used to be about as cool as shuffleboard. Well, we better keep our eye out for a shuffleboard resurgence, because Susan Sarandon made ping pong hot. The SPIN clubs have popped up around the US and now Toronto to bring a little friendly competition to cocktail hour. This 12,000 foot space has 12 ping pong tables, 2 fully licensed bars, a cocktail menu, a full food menu and a private party room. If you have no idea what you are doing, lessons are available. If you definitely know what you are doing, you may want to consider a membership. Refuel with their "elevated street style" snacks, which change seasonally.

Recommended for Best of Toronto's Entertainment District because: Ping pong coupled with a night club is the nightlife equivalent of the jock and the nerd becoming friends. We like it.

Courtney's expert tip: This is a block outside of the official Entertainment District radius. Please forgive us. We think a spirited game of ping pong is worth it.

Read more about SPIN Toronto →

TIFF Bell Lightbox
Photo courtesy of Twiggy Premi, courtesy of TIFF

The TIFF Lightbox is one of those places that helps to solve the conundrum "I'm bored!" without turning to your Smartphone. This building is set up to allow you to watch all of the film festival favorites, as well as the fantastic films that slip under the radar when the next Avengers movie dominates the box office. There are snacks (guacamole instead of popcorn should become a thing everywhere) and they do not frown at people who see wine as a perfectly viable concession snack. Look around you and you may see a celeb watching their own film under the radar. Do as the Canadians do and play it cool.

Recommended for Best of Toronto's Entertainment District because: Wine and cheese-ing while you watch a movie is a pretty civilized way to spend some free time.

Courtney's expert tip: The two restaurants attached - Luna and Canteen - are suburb. If you have free time, bring dinner and a movie back into style.

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Meet Courtney Sunday

Courtney Sunday has lived in England, Switzerland, Canada and the US, finding her way into the professions of freelance writing and yoga teaching in between travel opportunities. She learned...  More About Courtney