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A hotel owner who knows the city well recommends her favorite restaurants, bars, and things to do.

Hungry for a weekend full of world-class art, diverse restaurants, and beautiful nature? You’ve come to the right place.

Three of the chef’s favorite places to eat.

Overview

The Dakota Tavern is Ossington Avenue’s infamous subterranean saloon, an open concept rock bar with glowing skulls mounted on the wall, barn doors leading nowhere, and high-backed whiskey barrel stools surrounding the old oak bar. The Dakota has one of the best beer lists in the area (whenever you offer 500ml bottles of Beau’s Dark Helmet for $10, I’m sold), a tuned-in crowd, and an always evolving live band list that rocks more often than not. Bonus points: the house band blows the barn doors open every Sunday evening, making the Dakota Toronto‘s best weekender.

Rock Lobster hasn’t been a proper restaurant for long. This Ossington eatery got its start at the Toronto Underground Market, a monthly event which allows non-pros with a flair for food to show off their chops to masses of hungered folks. When their lobster rolls drew rave reviews and hour-plus line-ups, Matt, the man behind the crustaceans, decided there was no turning back. Although they serve lobster done every which way (poutine, bisque, mac ‘n’ cheese, topping steak) the rolls remain a personal favourite. Tucking hard shell Atlantic lobster into a grilled and buttered hot dog bun, the goods are served warm with a handful of chips and a dill pickle on the side. What’s not to love?

While the Dundas West strip has become increasingly cluttered come nightfall thanks to the run off from Ossington, there are still some spots where you won’t be jostled by a 19-year-old for the bartender’s attention. Plenty wee spots offer their own charm, but Black Dice Cafe has a vibe all its own. Located a bit further west (”It’s too far to stumble in heels!” I imagine said teenager yelling), BDC is a super nifty Japanese rockabilly bar. Come nice weather, the whole front of the bar is opened to the street; inside, patrons nurse Japanese whiskeys or sake-based cocktails while perched on the delightfully retro furniture, complete with lamps adorning the tables. A pinball machine holds court in a corner; a real jukebox entices barflies to use their coins to benefit the good of all. Did I mention they do yakitori and chips and dip? They do chips. With dip. So all the bases are covered.

I don’t know of many places where you can grab a coffee, read a magazine, pull a pint, flip a tractor tire, swing a sledgehammer, and finish off with an organic wheatgrass and kale smoothie, but then I don’t know many other places like the Academy. There are no Cowardly Lions here—this place is billed as a hybrid CrossFit/functional lifestyle outfitter, and every employee I met could kick my ass. This is an atmospheric place in the heart of Hipsterville, well worth a visit if you’re wandering one of Toronto‘s coolest neighborhoods and in need of a quick fitness fix—and a great cup of Joe—before hitting your next destination.

Williams Craig Design is one of the most impressive and inspiring design spaces in the city, and it looks and feels completely different with every visit. The studio offers design services for retail, corporate, and, most importantly, residential clients—which means Average Joe can pop in and benefit from the designers’ work.

Check out vintage boutiques, designer shops, and more discoveries in Toronto’s dynamic retail scene on this four-day itinerary.

Walk down Ossington any afternoon and you are bound to encounter a mysterious snaking line emerging from a rather nondescript space. Despite the fact that this is Toronto, not Reykjavik, locals have been queueing up Scandinavian style to get their grabby paws on this popular treat: Bang Bang’s ice cream sandwich. Small batches of creamy goodness are turned out at this shop along with a roster of fresh-out-the-oven cookies, Hong Kong egg waffles and matcha chiffon cake — for those who really wish to step out of the box. Ice cream flavours are listed sky high and veer from the interesting (b’day cookie dough ice cream) to the completely unique (brown bread and beer). Match up with your sandwich-making device of choice and get prepared to swoon. The line? Yes, it’s worth the wait.

This charming jewelry boutique on Ossington features one-of-a-kind pieces that incorporate both vintage sensibilities and modern styles. Finished items set with semiprecious stones are displayed alongside loose beads and trinkets that the owner will transform into craveworthy baubles. If you don’t know what to do with a broken heirloom, Anice will bring it back to life. Despite the mash-up of materials, the pieces are quite delicate and prove easy to wear or receive as a gift. The shop occasionally holds jewelry-design workshops.