Toronto has all but shaken the identity crisis that once plagued it. It’s blossomed from those awkward teenage years (and the questionable haircuts that came with them) into a charming and poised adult. Ontario’s capital city is officially in Cool Kid territory, defined by distinct and diverse neighbourhoods, each buzzing with unique eateries, boutiques, and culture.

As the eyes, ears, and taste buds arrive in town for TIFF, Toronto gets another opportunity to flaunt its newfound confidence.
Here are some of the latest—as well as the most essential—eats, drinks, and indulgences in town.

By Chris Metler

FEED YOUR DRIZZY FIXATION


Some estimates suggest Toronto’s homegrown hip-hop hero, Drake, may be responsible for five per cent of the city’s $8.8-billion tourism economy. Appropriately situated then in the Financial District is Pick 6ix, Drake’s collaboration with chef Antonio Park. More figuratively, there’s Drake Mini Bar, a pint-sized hangout that represents the latest expansion of the Drake Hotel’s multiplying mini-empire.

YORKVILLE GETS BETTER — AND BIGGER


Last November Hermès moved into a two-level unit on Bloor Street West, doubling the size of its previous digs and introducing handcrafted hockey sticks and other Toronto-exclusive products to its inventory. In May, just a block north on Yorkville Avenue, hospitality king Charles Khabouth cut the ribbon at his umpteenth upper-tier dining destination: Sofia, an Italian resto-bar oozing with swank. Next door, Taglialatella Galleries opened its first-ever Canadian outpost, focusing on the Pop Art movement. And soon on the way to the high-end area: Alo Bar Yorkville, the third address for Canada’s #1 best restaurant, ALO; gourmet grocer Eataly, occupying a palatial 50,000-square-foot residence; as well as Versace’s debut Canadian flagship.

SPEAKEASY-ESQUE


Gift Shop, an intimate 18-seat cocktail bar on lower Ossington, stealthily slings quality bracers out the rear of a men’s grooming parlour, Barber & Co. Nearby, hidden behind a tiny, pink bodega in Dundas West, Mahjong Bar is a secretive (and sprawling) cocktail spot that pairs its glowing red ambience with neon-lit libations.

LONG-AWAITED ‘LISTENING MUSEUM’ OPENS


The Museum of Contemporary Art will open the doors to its new space on September 22 with inaugural exhibitions including Believe, a multi-artist showing that investigates how personal opinions and beliefs influence the world we live in.

FEELS LIKE HOME


The Anndore House, just south of Yonge and Bloor, has undergone a multimillion-dollar facelift, and it shows. Modern services like a custom-designed app that lets guests live like locals by sharing staff’s favourite hot spots in the city, takes hospitality next level, while ground-floor restaurant Constantine reunites the duo behind Dundas West’s La Palma and Campagnolo. Meanwhile, the Broadview Hotel—a comparable restoration project—accomplishes more than merely anchoring Riverside and Leslieville. It’s a vibrant meeting point for Toronto natives and a trendy home base for visitors.

DINNER AND A $HOW


While securing a ticket to Après Noir doesn’t come cheap (prices reach $3,000 a head), the ultra-exclusive monthly concert-dinner series imports the best entertainment acts available—magician David Blaine performed on August’s bill, and Drake’s coming in November—then pairs them with universally acclaimed kitchen kingpins. The result is an all-encompassing evening conceivably worth the sky-high cost of admission, assuming you’re inclined to splurge.

OOH LA LADURÉE!


Aficionados of opulent Parisian patisserie bided their time until Ladurée’s arrival, but the inaugural boutique of the purveyors of fancy macarons proves people weren’t waiting in vain. Everything about the experience is perfectly French. (Thankfully, round-the-corner lineups at its Yorkdale shop have subsided.)

BUON APPETITO


If you can track down Famiglia Baldassarre, a members-only eatery nestled between the Wallace Emerson and Wychwood Park ’hoods, try the agnolotti Piemontesi with braised beef, butter, and sage, and taste why this hidden gem is Toronto’s best-kept culinary secret. Nearby, but slightly more easy to find, is Rob Rossi’s sharing-style Giulietta at Dufferin Grove.

CREATIVE KING WEST


Boasting a private social club and on-site Social-Architect/event-concierge, experimental 49-storey tower Empire Maverick will shake up condo land when the residential/leisure complex is complete. Until then, King West visitors can swing by Akira Back’s Michelin-starred eponymous outpost in Bisha Hotel, where the esteemed chef serves up Japanese cuisine and Korean flavours, all with a Canadian twist.

HERE’S TO YOU, MRS. ROBINSON


Inspired by the co-founder of Sugar Hill Records—not Simon & Garfunkel’s enduring chart-topper—Mrs. Robinson is a vibrant throwback to old-school cocktail bars. Patrons at the Little Italy haunt can enjoy live bands or DJs spinning tunes, all while sipping soulful cocktails like the vermouth amaro-friendly Little Priest and hop vodka-fuelled Second Chance Machine.

WINE NOT?


A phenomenal tasting menu originally earned Don Alfonso 1890 its Michelin stars on the Amalfi Coast; however, the ambitious wine cellar—counting 650 bottles—steals the show at its Old Toronto entry. Head sommelier Alexander Powell will ingeniously pair Old and New World selections for a hundred bucks.

Reel-y Good Drinks


Stop by Shangri-La Hotel, Toronto during the festival and enjoy one of three limited-edition film-inspired cocktails. Developed by the hotel’s head bartender, Chris Rail, the playful drinks include: After Midnight, a twist on the classic penicillin; Double Feature, which uses a Skittles-infused Grey Goose vodka and Chambord; and Last Kiss, a jalapeño-and-strawberry-flavoured concoction with tequila, whisky, and sake.

ART GONE URBAN


The Art of Banksy exhibit may have just concluded its well-attended run, but discerning collectors of contemporary street art crusaders can still get their fix at Moss Park’s historic Gallery 181, or at ILLEgallery. The former specializes in graffiti photography, painting, and sketch, whereas the latter spotlights urban artists across Canada and abroad. Neither lose the medium’s fundamental gritty essence.

WELCOME TO SILICON VALLEY NORTH


Toronto ranks among the planet’s premier urban innovation hubs. From September 21 to 27, the Elevate conference will bring in no fewer than 250 host venues, 300 electrifying speakers, and 10,000 visitors, making it the biggest domestic festival of its kind. What better way to mark Canada’s Tech Week?

MOMOFUKU REINTERPRETS THE STEAKHOUSE


Kōjin is David Chang’s latest Toronto establishment, located on the third level within Momofuku Toronto. The emphasis at Kōjin shifts from Asian to fire-singed Latin American fare, with seasonal Ontario ingredients receiving mouthwatering priority.

BUT FIRST, COFFEE


Italian architects Goring & Straja transformed storied TIFF mainstay, the Cumberland Four cinema, into a 14,000-square-foot flagship Nespresso Boutique Bar. The grand café, lounge, and showroom welcome festival-goers in staggering numbers, only now to enjoy the art of espresso rather than film.