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.


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.

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.


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. It is a perfect stop on the Toronto tourism train. The 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.

The Porch
Photo courtesy of Porch Toronto

As Toronto's downtown gets more and more crowded, there has been a trend towards sprinkles of 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.

Real Sports Bar
Photo courtesy of Real Sports Bar Facebook page

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.

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.)

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.

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. Tables book from $15 an hour on Mondays to $70 an hour on Saturday night. It is advisable to book early as many people take the game seriously. There is a menu with the usual Canadian bar snacks (late night poutine, anyone?) but a local and ethical sensibility. Drinks can be as fancy as champagne or as low key as a punch bowl with 9 oz of alcohol added. Whether or not the punch will improve your game is yet to be decided.

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 transforming into a 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.


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