In recent years, Toronto has become something of a cultural behemoth. Two of its most famous residents, Drake and The Weeknd, have dominated the charts for the best part of a decade now, coining a new nickname for ‘the 6ix’ along the way. Meghan Markle calls Toronto her second home, and the universally adored, uber-cool Keanu Reeves grew up here, too.
What’s more, the book which led to the 15-Emmy award winning show the Handmaid’s Tale was written here by Toronto resident Margaret Atwood, and the city’s Art Gallery of Toronto is among the most revered in all of North America.
Canada’s largest city, Toronto is often described as a more modern and more manageable version of New York. It’s also one of the most multicultural cities in Canada and people from all over the globe have forged communities here, leading to a fascinating food and arts scene, and a warm, welcoming atmosphere.
This dynamism and drive leads to a vibrant, youthful energy in the city just perfect for a night on the town. So, that’s exactly what we’re doing; for the IDEAL night out in Downtown Toronto, here are 8 places you must visit.
Kick Off With Brunch Cocktails At The Broadview Hotel’s Café
Right, let’s start this proper Toronto adventure with a bit of sophistication before we head to the races. The Broadview Hotel in the trendy Riverside neighbourhood is our first port of call, but we’re not going straight to the rooftop – save that for later, perhaps on another night out entirely.
Instead, we’re beginning our day at The Café on the ground floor, which does a brilliant weekend brunch service that’ll set you up nicely for the afternoon ahead at Woodbine. Arrive around 11:30am and ease into the day with their excellent brunch cocktails – the Caesars here are legendary (that’s Canada’s superior version of a Bloody Mary, made with Clamato juice, and trust us, it’s better than it sounds).
The Victorian-era building provides a gorgeously atmospheric setting, with soaring ceilings and massive windows flooding the space with natural light. It’s the sort of place that makes you feel properly grown-up whilst still being relaxed enough for what is, essentially, day drinking.
Their brunch menu is a treat too – the ricotta pancakes are positively cloud-like, whilst the smoked trout benedict offers a Canadian twist on the classic. But don’t go too mad; remember, we’ve got races to bet on, beers to sample, and a full night of eating ahead. Think of this as your elegant foundation for the controlled chaos to come.
By 12:30pm, you’ll be perfectly primed – well-fed but not stuffed, lightly buzzed but still sharp enough to pick a winner at the track. Call that taxi to Woodbine, and let’s get this Toronto night out properly started. Well, afternoon first, then night out. We’re pacing ourselves like proper professionals here!
Pregaming At The Woodbine Racetrack
Okay, we realise we said ‘downtown’ and we understand we invited you on a night out, but as any seasoned sessioner knows, the party always needs a little pregaming to get you in the mood.
So, we’re starting things early at the Woodbine Racetrack, which is around a half hour’s drive northwest of Downtown (a taxi should set you back around $40, which is roughly £25).
Woodbine offers world-class thoroughbred racing, with races held four days a week on Thursdays, Fridays, Saturdays and Sundays. Thursday’s first race post time is at 5:30pm, Friday at 4:30pm, and Saturday and Sunday at 1:05pm. If you’re truly playing the long game, the track also hosts Canada’s biggest racing event, the King’s Plate, on 16th August 2026.
On site, you’ll also find the Woodbine Casino with 24/7 slot games and tables if you fancy an afternoon flutter (always gamble responsibly). Alternatively, the Canadian Jackpot City Casino has online slot machines, poker, and live dealer games.
Begin With Canadian Craft Beer In Kensington Market
With the pregaming hopefully leaving you both in pocket and drink, we’re heading downtown to begin our night out at Kensington Market, a manageable cab ride from Woodbine.
Rather than being a genuine, fully fledged bazaar, Kensington Market is actually a highly strollable, eminently enjoyable neighbourhood, home to boutique shops, hip restaurants and bars, and a bohemian vibe.
Here you’ll see some pretty astonishing graffiti and street murals, as well as street performers doing their thing at all hours of the day. For excellent craft beer, head to Bellwoods Brewery just a short walk away on Ossington Avenue, which does some superb craft beers and has a terrace just perfect for a cold glass in the warm sun. For a bit of added fun, we just love their tasting flight of four beers, which gives a neat little insight into the intriguing flavours on offer here. Cheers!
Enjoy Dinner At One Of The Ossington Strip’s Globetrotting Eateries
You’ve probably worked up a pretty strong appetite by now, and just a short stroll from Kensington Market is arguably the best place to eat in the city, Ossington Avenue.
Commonly referred to as the Ossington Strip, the sprawling street is occupied by rows of cute bakeries and cutting-edge bars, as well as a whole host of restaurants that represent the multicultural make-up of Toronto.
Some of our favourite places to dine include Pho Tien Thanh, a buzzy no-frills Vietnamese joint that cooks the country’s traditional noodle soups with generosity and precision. It gets busy, so expect to share a table with strangers. Hey, they might even want to join you on the next leg of your ideal night out in Toronto!
Or, how about La Cubana, purveyors of Cuban comfort food just perfect for soaking up the beers you’ve accrued along the way so far. The craft Cuban cocktails here are fantastic.
Alternatively, for a reinvigorating hit of spice, then right at the top of Ossington Avenue, on St Clair Avenue, you’ll find Itacate, a butcher’s shop/restaurant hybrid that does some of the best meaty Mexican food you’ll try anywhere on the planet.Here, the pambazo, a fried sandwich filled with house-chorizo, potato, cheese and crema, is a must-order. As long as you’re not wearing a white shirt, that is; the sandwich is dipped in guajillo chilli sauce before being fried, making it a totally indulgent but incredibly messy affair. Pro tip? Keep the sandwich in the plastic bag it’s served in while you eat it.
Indulge In Dessert At Bang Bang Ice Cream & Bakery
Food coma be damned; we want dessert and we want it now. Back on Ossington Avenue, Bang Bang Ice Cream and Bakery are doing some of the most exciting ice cream in the city, with some seriously outlandish flavour combinations getting sandwiched between housemade cookies.
Yep, not satisfied with ice cream alone, we’re having Toronto’s finest ice cream sandwiches for dessert. Ours is a lychee, rosewater and raspberry. What are you having?
Read: 5 travel tips for Canada first timers
Splash Out On The Iconic ‘Smoked Manhattan’ At BarChef
Phew, that’s enough food to see us through ’till Christmas, but we’ll walk it off, heading east along Queen Street to our next pit stop.
Don’t be concerned by the name of the cocktail bar we’re heading to next, because you won’t have to eat another meal at BarChef. Rather, the name is simply suggestive of the intricate nature of the flavour combinations that populate the bar’s drinks menu, with molecular gastronomy and a fair bit of kitchen wizardry playing a part in crafting the best cocktails in Toronto.
All syrups, infusions and bitters are made in-house by the chefs/bartenders/whatever you want to call them, and this lends real gravitas to the cocktails. The most famous order here is the Smoked Manhattan, which has been infused with the flavours of gently burning vanilla and hickory. It arrives in a jar circulating with the aromatic smoke, and a bill for $50 (let’s hope you won big at the racetrack). Man, is it good, though.
Dance The Night Away & Make Connections At Love Child Social House
Now we’ve put some distance between dinner and the night’s conclusion, it’s time to put on your dancing shoes (you did pack your dancing shoes, right?) and head to Love Child Social House, just 750 metres from BarChef.
By day, Love Child is a co-working space for creatives, titans of culture, and, well, anyone with a credit card, but at night, the room transforms into one of Toronto’s hippest clubs. It’s a casual and classy kinda place, rather than the type of club where you gather round a bottle of Grey Goose and stand around silently, and it’s all the better for it.
Do be aware that there’s a 23+ age policy here on Saturdays. Perhaps it should be named ‘Love Mid-to-Late Vicenarian’. And with that overly complicated attempt at a dad-joke, we probably wouldn’t be let into the club anyway. We’re off!
Wind Down With Late-Night Eats At Rol San, Chinatown
After all that dancing at Love Child Social House, you’ll likely be craving something substantial to cap off the evening, and there’s no better way to end a proper Toronto night out than with dim sum at Rol San in Chinatown.
Just a quick taxi ride from King West (or a refreshing 20-minute walk if you fancy clearing your head), this Spadina Avenue institution stays open until 2am Sunday through Thursday, and until 5am on Friday and Saturday nights – making it the perfect finale to your Downtown adventure.
Rol San is something of a Toronto legend, beloved by everyone from university students to celebrity chefs for its no-nonsense approach to Cantonese cuisine. The fluorescent lighting and basic décor might not win any design awards, but who cares when the har gow (prawn dumplings) are this good at 2am?
The late-night menu features all the dim sum classics – siu mai, char siu bao, and those addictive sticky rice parcels wrapped in lotus leaves. But the real move here is ordering the congee, a silky rice porridge that’s basically a warm hug in a bowl and the ultimate hangover prevention tool. Get the one with preserved egg and lean pork if you’re feeling adventurous, or stick with the seafood version for something a bit more familiar.
The best part? The bill will barely make a dent in your wallet, especially compared to that $50 Smoked Manhattan earlier. You’ll leave satisfied, slightly more sober, and with the perfect end to your Toronto night out – watching the city slowly wake up as you head home with a full belly and some brilliant memories.
For something totally different in the Great White North, check out these 9 things to do with the kids in Downtown Vancouver. Go on, you know you want to…
