Toronto the Local Way

Tips on the city's best art, brunch, shopping and more, from those who know best.

A Cultural Melting Pot

Think “international travel” and Toronto, Canada might not top the list — but look closer and you’ll discover that this is actually one of the most culturally diverse cities in the world. In fact, half of the residents in this city, the fourth largest in North America, were born in a country other than Canada.

As a result, this bustling metropolis on the edge of Lake Ontario is a melting pot of language, fashion, food, art and history, split up into distinct neighborhoods, each with its own style. Take a walk and see history expressed in the architecture, with Bay and Gable Victorians leaning up against refurbished lofts made of steel and glass. Wander down side streets to find secret markets and museum-quality artwork splashed across the walls.

Combine all of this with the natural beauty of the Niagara Region in a full range of seasons, and there’s no doubt it’s high time to visit the U.S.’ friendly neighbor to the North.

Meet the Locals

Still don’t believe us that Toronto is worth a spot on your bucket list? Then perhaps you’ll heed the insights of two tried-and-true locals.

Meghan Symsk has been in the music industry for decades, most notably as part of the management team for Rush, arguably Canada’s most iconic rock band. And even though she’s hit the road for a large portion of her career — at last count she’s visited 25 countries — nothing can entice her out of the vintage Danforth neighborhood apartment she’s lived in for 20 years (“How would I ship my chandelier?” she laments. “It took me 10 years to find it!”)

As the founder of Treeline Catering, Joshua Hendin has helped to make the perfect wedding a reality for many Toronto brides. He’s also catered for Gorbachov and Al Gore and counts Facebook and Cirque de Soleil among his clients. A dedicated adventurer and philanthropist, he can’t imagine a home base better suited to him than the one he has here in the Golden Horseshoe.

Let’s hear what a music industry insider and the perfect party host have to say about hanging out in the city sometimes known as the 6ix. (Fun fact: the nickname is based on the city’s 416 area code, and the fact that it was at one point broken up into six areas.)

Best Place for Perusing Art

St. Lawrence Market, which National Geographic named the world’s best market in 2012, features a gallery space with excellent rotating exhibits, plus cooking classes and vendors selling prepared foods, fruits, vegetables and cheeses. “Do yourself a favor,” Joshua says. “Start at the back of the market and work your way forward.”

With its stellar collections and revolving exhibits, there’s something for everyone at the Royal Ontario Museum of Art. “If I have guests visiting and I end up having to go into work,” Meghan says, “I drop them at the ROM and they’re set until I’m done.” Notable exhibits at the museum have included “Here We Are Here: Black Canadian Contemporary Art” and a feature on Christian Dior presented by Holt Renfrew.

The latter Meghan had to see for herself. “The textiles, the embroidery, the dresses!” she exclaims. “I would have taken all of it home if I could have.”

Best Night on the Town

Josh has a well-rehearsed game plan. “I like to start at a pub,” he says. “One of the older ones in the city like The Irish Embassy.” From there he’ll stop in at Alo before making the short walk to BarChef for a glass of Absinthe, “to really get things revving.” In the summer he winds down with the fellas and a good cigar at an impromptu social club he calls Chairs on King, a street party held on King Street in front of his loft, where they set up directors chairs on the sidewalk.

Meghan recommends finding yourself amidst the salvaged wood and exposed brick at Pinkerton’s Snack Bar, to see if you can stop your shoulders from shaking. She says the music is so good “that impromptu dance parties have been known to break out in the aisles between the tables.” Be sure to wear your dancing shoes.

Best Joint for Live Music

Horsehoe Tavern has been a Toronto staple since 1947.

Music is Meghan’s job, but it’s also her passion. She’s seen live performances in tattoo parlours and at the back of record stores, attending shows at every venue from the Danforth Music Hall to Lee’s Palace. And while she can’t wait for the revamped Massey Hall to open, her heart always has and always will belong to the Horseshoe Tavern. “And Tyrone the doorman,” she adds with a smile.

Opened on Queen Street in 1947 as a prime rib place serving music on the side, the ‘Shoe has hosted everyone from Willie Nelson to the Ramones. Meghan has watched fans crowd-surfing to Brody Dalle, waving lighters for Elliott Smith, and being mesmerized into silence at sold-out shows for The Tragically Hip.

More likely to be found waving three fingers of scotch in a rocks glass than holding up a three-finger rock salute, Joshua prefers the retro stylings of the intimate Orbit Room, hiding at the top of a set of stairs off College Street. “They get incredible talent for such a small space, from Lady Gaga's backup band, to horn players that have toured with BB King.”

Best Summer and Winter Spots

Winter is the ideal time to hit the ice at Natrel Rink.

Joshua prefers to spend summer months beside the bonfire at the isolated Gibraltor Point on the southern tip of Toronto Island. With few residents and no cars, it can get really dark out there. “It’s like camping in the city,” he says. And the best kind of camping includes a good ghost story, like the one involving the 1815 murder of the Gibraltor Point lighthouse keeper. Still standing, it is the oldest existing lighthouse on the Great Lakes.

Meghan agrees, but she also loves the Bovine Sex Club’s rooftop patio on sunny days. Not as kinky as it sounds, this Dada-esque club is known for its eclectic mix of cutting-edge music.

As for winter, it’s for doing outdoorsy things. Meghan loves the toboggan hill (also known as downhill sledding) in Riverdale Park East on Broadview, while Joshua has been spotted ice skating at the edge of Lake Ontario, at Harbourfront Centre’s Natrel Rink with his extended family. In a cashmere overcoat, naturally.

Best Fancy Dining

Buca makes its own cheese and charcuterie, and serves pastas featuring ingredients like caviar and truffles. “Even my Italian colleagues swoon,” Meghan says, adding that, “You might have to unbutton your pants halfway through the scialatielli but it is so worth it.”

An adventure-seeker who doesn’t mind getting his hands dirty, Joshua is also a man who loves the finer things, like seasonal ingredients and gifted sommeliers. “I mean, a French tasting menu on the roof of an old Victorian. What’s not to love at Alo?”

Best Cheap and Greasy Dining

An insatiable fan of guacamole, Meghan says the guac at Playa Cabana Cantina can’t be beat. “And there is that perfect salt-to-lime ratio on the chips.”

Joshua is happy that Avenue Open Kitchen on Camden Street hasn’t changed much since the fifties, in terms of prices and the poutine fries, a staple of Canadian cuisine. Plus, he says, sometimes you need a Montreal smoked meat sandwich, and this is the place to get one.

Local Team to Root For

Toronto Blue Jays — The Blue Jays hit home runs at Rogers Centre.

Whether you’re into shooting hoops, throwing hand signs at the catcher from the pitcher’s mound or hitting slap shots, Toronto has you covered; its collection of world-class teams includes the NBA Raptors, MLB Blue Jays and, of course, NHL Maple Leafs.

Still, it seems like Joshua is more interested in repelling down the side of mountains in British Columbia than organized sports back home. “I’m going to let Meghan answer this one,” he says. “I can try to name a current player on each of these teams, but I have to admit, I’d be guessing.”

Here’s an example of that Canadian diversity, because Meghan can’t pick just one.“I love them all and I go to games as often as I can. But given that you’re asking me about this on opening day, I’ll go with the Jays.” Toronto Blue Jays for the win.

Best Boutique Shop

Meghan loves 69 Vintage for one-of-a kind designer finds and KASpace for ethical vegan fashion. (And Elte, of course. We can’t forget that chandelier she’s so attached to.)

Joshua, who has walked the runway for Toronto Men's Fashion Week in wing tips and a fitted suit, says, “Sydney’s is the best men’s shop in the world.”

Best Brunch Spot

School takes its theme seriously. Hours are laid out like a classroom schedule, and the menu is divided into sections called Extra Credit, First Period and Principal’s Office. As for the food, it gets an A+. Meghan recommends in particular the brunch classics; “it’s the Super Cheesy Bacon French Toast all the way,” she says. The delectably unhealthy dish is served with, what else, Ontario No.2 maple syrup, the nectar of the Canadian Gods.

Joshua is partial to Smith on Church Street in the center of Toronto’s LGBTQ community, an area that he affectionately refers to as “the Gaybourhood.” At Smith, the charm is in the details. Interesting offerings like pistachio waffles are printed on art-directed menus, and top floor patrons are treated to views of the street’s historic Victorians.

Best Cup of Joe

Because good brunch is an institution in Toronto, there are often lines around the corner. The best way to beat those brunch blues is to grab coffee first.

Meghan hits Mercury Espresso Bar in the east end of the city, known as Leslieville, for a cappuccino made with socially responsible beans. Joshua heads west to Ezra’s Pound to drink a shade-grown organic cortado at the foot of Casa Loma, the landmark museum that was built as a private residence for financier Sir Henry Mill in the early 1900s.

Best Location for a Day Trip

Meghan’s family still lives in the house she grew up in, so she spends a lot of time making the hour-long drive to the lakeside hamlet of St. Catharines to spend time with her nieces. Instead of zoning out on the freeway, she follows Highway 8 along the lake.

“It’s a beautiful leisurely drive, and if you’re really taking your time, you can stop into Henry of Pelham or Tawse Winery” — two of a hundred local wineries in an area The New York Times calls “a wine region of depth, diversity and distinction.”

One of the reasons Joshua lives in the heart of the city is so he doesn’t have to drive if he doesn’t want to. Toronto traffic is notorious and because of that, sometimes “nowhere is good to drive,” he says. “If I had to pick, it would be a motorcycle ride to the Portage Store in Algonquin Park for apple pie.”

Best Cocktail

The menu at BarChef is built to challenge conventions. Unique infusions and syrups are all made in house using spices like caraway, cardamom and cumin. Joshua’s favorite on the wizardly menu is the Vanilla Hickory Smoked Manhattan made with Crown Royal Special Reserve. It “tastes like cherries and black licorice,” he says.

Meghan, on the other hand, has rarely met a Moscow Mule she doesn’t want to get kicked by — so much so that she was hard pressed to pick a single favorite and passed on this question.

Best Secret Spot

House of Strombo is Meghan’s favorite spot kept on the down-low. “George Stroumboulopoulos is a former MuchMusic VJ who hosts a live concert series in his downtown Toronto home,” she says. Past guests have included Barenaked Ladies, the Arkells and Lights. Getting an invite to one of these is like getting a golden ticket, though the events are less of a secret now. George made a deal with Apple music last year and now represents the platform’s first Canadian content.

According to Joshua, if you're trying to get away from everyone, and you can't leave the city limits, Toronto Island is the place to go. “From the far side, with the shoreline trees blocking any view of the city's glow and the expanse of Lake Ontario out in front of you, it can feel like you’re in the middle of nowhere.”

Best Event of the Year

According to Meghan, the best event is her birthday night, which she celebrates at Canada’s famous Barbarian’s Steakhouse every year. With private dining rooms — including one in a wine cellar surrounded by 15,000 bottles of the world’s best wines — and a secret top-floor deck, this family-owned business makes revelers feel “like they're having a party in a private home.”

For Josh, it's about all that jazz. “There’s a ton of great blues and funk being played the week of the The Toronto Jazz Festival,” he says. “Actually there’s just generally awesome live music being played all over the city.” Running from June 22 to July 1, this year’s lineup will include performances by Seal, Alison Krauss, Herbie Hancock, Bettye LaVettte and Holly Cole, just to name a few.

Why Toronto is Objectively the Best City on Planet Earth

For Josh, Toronto is all about the people. “I choose to live here because every single day I meet with people who have modern minds, and who are extremely ambitious, stylish and well traveled. I am inspired by them.”

Meghan has also found her inspiration in Toronto, but for her — and let’s be honest, for a lot of people who like to rock, not just Canadians — the reason she thinks this city reigns supreme is because, “we have Geddy Lee.” (He’s the lead singer of Rush.)

That settles it. Canadians are just as loyal, supportive and nice as everyone says they are. And who wouldn’t want to hang out with people like that? Sounds like it’s time for a trip to Toronto.