As one of the world’s most multicultural cities, Toronto’s distinct neighbourhoods are as diverse as its people – each with its own culture, customs and cuisine. The history of how these neighbourhoods came to be is just as compelling. The Junction was its own city before being annexed to Toronto and becoming home to trendy craft breweries. The upscale eateries of the Distillery District are located in buildings that once housed the largest booze producer in the world.

Thanks to gentrification, many areas of the city have an old-world-meets-new kind of charm. A perfect example is Dundas West; a street lined with a mix of up-and-coming dining hotspots and old-school Portuguese bakeries.

Those with an independent streak will appreciate the best dive bars in Kensington, the little market that stood its ground against a Walmart that tried to muscle its way into this neighbourhood. We’ve rounded up the best experiences, sights and eats from Toronto’s most notable neighbourhoods.

Waterfront

Next to iconic waterfront cities like Chicago and New York, Toronto’s lakefront facade pales in comparison, or it did until recently. For years, Torontonians were drawn to the harbour only as a way to get to the Toronto islands for a quick getaway. Our harbourfront has gone through a dramatic transformation in the last few years, and has blossomed into a buzzing strip that attracts local and international visitors. Today it is one of the best spots in the city for live music and international food festivals, all with the backdrop of Lake Ontario.

During the summer season, the Harbourfront Centre hosts a number of international events that highlight food from around the world. During the events, the outside food pavilion functions as a home for vendors who pop up with traditional menus, so grab some takeout and head to the expansive boardwalk.

Queens Quay is the main strip that connects Toronto’s waterfront and you’ll find many spots for quick bites and lakeside meals. Take in dim sum with a view at Pearl restaurant, one of the last cart-style options in the city, where an assorted menu of Chinese brunch is served. Families will drive in from uptown, not just for the food – the dining room has a panoramic view of the islands.

If you prefer beer, head to Amsterdam Brewhouse’s large-scale brewery and restaurant where they offer an extensive contemporary beer hall menu paired with over a dozen in-house beers. Across the street from the brewery, Indian Roti House serves fiery east Indian-style curries bundled up in large roti-wrapped pouches. Get the butter chicken or channa roti.

Amsterdam Brewhouse's patio

In the “new” category, Loch and Quay has become a popular spot for those health-conscious eaters with its menu of grain bowls. They also have a great burger on the menu. After dinner, head over to Touti Gelati for seasonal gelato.

The sunsets at the waterfront are magical and they’re best enjoyed near the water. If you’re in the mood for craft beer and whisky, hit The Slip patio by Box Car Social.

Kensington

In a town where nothing stays the same, Kensington Market has become something of a maverick with a proven track record of standing up to the big guys and winning. Even Walmart couldn’t break into the quirky neighbourhood, which has mostly held on to its character and charm despite frequent attempts to gentrify.

The real jewel in Kensington’s crown is its walkability. If ever there was a place for a food crawl, it’s here, in this wonderfully eclectic market made for strolling. It might not be one of Toronto’s hidden gems (weekends often see visitors spilling from the sidewalks), but there’s a good reason why so many visit.

The neighbourhood’s deep multicultural roots mean that a trip to the market takes our palates across borders and through various cuisines. Hop across the globe with Chilean treats from Jumbo Empanadas or fusion dishes like a jerk chicken panini from Rasta Pasta.

If there is a unifying theme to Kensington Market, it’s Mexican food. Get in line at Seven Lives for a Baja-style taco, or head to El Rey for the upscale version and a wide selection of mezcal. El Trompo, one of the market’s longest standing vendors, has been serving tacos for over a decade. Take the short walk over to Augusta Avenue to sample their signature al pastor offering with a horchata on the side.

And Mexican food in the market also comes stuffed between bread. Torteria San Cosme has their take on the popular sandwich from Mexico City, called tortas, in roughly 10 variations. Spend some time on the patio at Ronnie’s, one of the city’s best dive bars. There’s no table service or food to be had here, so guests are definitely in the business of drinking. To cure your thirst, you’ll have to step inside and navigate the darkness – pick your poison from one of the draught beers on tap (adorned with creepy doll heads).

Toronto’s waterfront has blossomed into a buzzing strip that attracts local and international visitors.

Round things out with a visit to Cold Tea, the neighbourhood’s ‘secret’ bar, very much in quotation marks. Wander through the grungy mall and head for the graffitied door hiding Kensington’s worst-kept secret. Once you’re inside, enjoy classy bar snacks, local beers, and – if it’s a Sunday – a sweaty, dance party that goes all afternoon and evening.

It might seem like heresy to classify Otto’s Berlin Doner’s tasty offerings as mere drunk food, but there’s something about their doner meat covered in garlicky hot sauce that begs to be eaten (or dropped) on your way home from a night at the bar with friends. Order the Veal and Lamb Döner Teller and nurse it as far as Spadina, where you can catch a cab. Or, if you’re not ready to end the night, stop in at one of the many brightly-lit Chinese restaurants in the area for dim sum and a nightcap.

Parkdale

Founded in the 1850s, Parkdale is one of Toronto’s oldest neighbourhoods. This west end district, south of where Queen West meets Roncesvalles, hasn’t always had the best reputation, and despite the growing influence of gentrification, its streets still have a certain grittiness. Tibetan, West Indian and North African enclaves, plus a newer influx of hipsters and, most recently, vegans, make Parkdale one of the city’s most interesting neighbourhoods.

Start your tour with breakfast at Skyline Restaurant for cozy diner vibes in vinyl booths, endless coffee refills and well-priced daily specials. Grab a slice of their house-made pie for dessert. Or save your sweet tooth for one of the indulgent creations at Craig’s Cookies who are known for combining homestyle chocolate chip cookies with treats like Pop Tarts and Mars bars.

Parkdale is home to one of the largest Tibetan communities in Canada and there are about seven restaurants in the neighbourhood specializing in this Central Asian cuisine. Each restaurant has go-tos, but you can expect a similar bare-bones ambiance and affordable and deeply delicious Tibetan food. There are many options for momos – fried or steamed dumplings with meat or veggie filling – but Loga’s Corner is definitely a strong contender for the best. Go easy on the house-made hot sauce, unless you’re a serious heat fiend.

The growing vegan influence in Parkdale is a big change, but no food crawl in the neighbourhood would be complete without at least one meatless meal. Doomie’s, in the rapidly-expanding Vegandale hub, offers a fast-food fix with its meat- and dairy-free takes on burgers, mac ‘n’ cheese, chicken fingers and other comfort food faves.

For evening drinks, sip on beautiful cocktails crafted by some of the city’s best mixologists at PrettyUgly Bar; or get a sunny taste of the tropics with Miss Thing’s retro tiki-bar style concoctions.

Greenwood 

Let’s face it, Toronto’s east side gets only sparse attention. The city’s west corners like Queen West, Dundas West and even King West are associated with cool and fun, but the east side has been regarded as a part of the city that lacks excitement.

The Greenwood-Coxwell corridor connects the city’s east side from the Danforth, all the way down to the lakefront and its diversity of cultures is the main attraction. Start on the Danforth where places like Al Mandi continues to serve traditional Middle Eastern dishes. El Sol specializes in the northern Mexican classics like fish stew and chicken mole. And, if you want Japanese comfort food, you need to head to Sakawa Coffee for curry and omurice.

Head down Greenwood Avenue to Wagstaff, a small industrial strip that is home to Left Field Brewery and Pilot Coffee. Pilot’s highly acclaimed beans show up in many cafés and restaurants around the city. Stop in for some cold brew or a pourover. At Left Field Brewery you’ll find a seasonally changing range of sours and inventive IPAs.

Walk a block further south to family-run Maha’s Restaurant. Maha’s is one of the only places in Toronto that serves traditional Egyptian brunch. Go early and be prepared to gorge on falafel and bowls of shakshuka.

Dundas West

While it seems like gentrification has become a defining feature of almost every Toronto neighbourhood in the last few years, there aren’t many places where the mingling of old and new is as pronounced as Dundas West. Also known as Little Portugal, the stretch of Dundas between Ossington and Lansdowne was the centre for Portuguese settlement in Toronto during the 1950s, ‘60s and ‘70s.

Today, you’ll still hear Portuguese spoken and see Portuguese men sitting on plastic chairs outside old-school sports bars, keeping watch over the neighbourhood; but this west end district has recently seen an influx of eclectic boutiques, hip bars and some of the city’s best restaurants. A full list of noteworthy places to eat and drink in Dundas West could easily be its own article, so here are a few highlights.

A proper exploration of Dundas West should take in a mix of old-school and new-school joints. There are a handful of good churrasqueiras – restaurants specializing in churrasco, a style of grilled meat popular in Portugal and parts of Latin America – but we think the best way to get a taste of the neighbourhood’s heritage is with a mid-afternoon bakery tour. The ultimate place to try Portugal’s iconic custard tart is a hotly debated topic. Check out Nova Era, Caldense and Brazil bakeries and conduct a taste test to determine which spot you think gets the wobbly egg custard, buttery shell combo just right.

SoSoFood Club is among our favourite recent openings. Part restaurant, part bar and part event venue, the early evening sees Soso serving stellar Chinese dishes in a retro space and then, as the night progresses, this buzzy spot transforms into a dance bar.

If it’s a Sunday, enjoy a sweaty dance party at Cold Tea that goes all afternoon

For Asian-inspired fare in a more low-key setting, head further west to Uncle Mikey’s. Despite its killer Korean-influenced dishes, the menu at Uncle Mikey’s is remarkably well-priced and it’s usually easy to snag a spot in the restaurant’s intimate interior.

It may not be Dundas West’s newest restaurant, but Enoteca Sociale’s relaxed setting, house-made pasta and wines by the glass make it another top choice.

You’re spoiled for options when it comes to post-dinner drinks, with Dundas West’s strip of quirky, hole-in-the-wall bars. With kitschy decor and a warm glow courtesy of red and white fairy lights, the Communist’s Daughter is as cozy and eclectic as they come. Live bands play on Saturday and Sunday evenings, occupying more of the bar’s already precious little space but if you can find a table, the ambiance is downright magical. Spend your evening soaking up chill vibes at the Daughter, or continue your bar crawl west to Black Dice, a charming rockabilly bar that channels 1950s Japan. The bar has an exceptional selection of Japanese whiskies, beers, cocktails and sake, plus a jukebox from 1958 and a cool pinball machine.

Distillery

There’s a refreshing old-world charm that pervades the Distillery District; a micro-neighbourhood made up of the Victorian red-brick buildings of the former Gooderham and Worts Distillery. Today, the pedestrian-only space is a great spot for art, shopping and delicious eats.

Madrina in the Distillery District

Saunter across the brick-laid streets to Mexican restaurant, El Catrin, and enjoy guac on their huge patio. Sister restaurants Cluny, a stunningly decorated Parisian bistro; Madrina, a Catalan tapas spot; and Pure Spirits Oyster House are also worth a visit.

Though the Distillery no longer makes whisky, small-batch vodka and gin are produced at Spirit of York. Another place to sample the hard stuff is Ontario Spring Water Sake Company, the first sake brewery in North America. Mill Street Brew Pub is the local spot to enjoy on-site brews.

If the Distillery District steals your heart, leave a love lock at the installation on Tank House Lane – or a snap for the ‘gram.

Willowdale

Willowdale, in North York, is a kaleidoscope of Asian culture with a slew of restaurants serving Japanese, Korean and Chinese food.

The takeout from VIPS Sushi will get the most bang for your buck – rolls are cheap, delicious and portions generous. Sushi Moto is a little higher priced than other spots in the neighbourhood but it’s well worth it for the quality and flavour. Also, meat dishes like the kalbi ribs are always tender and juicy. This spot picks up after midnight with large groups ordering up small wooden boats overflowing with sashimi.

From Sheppard to Finch, this stretch of Yonge Street is lined with ramen joints, from bigger names like Sansotei and Kinton to lesser-known gems like Konjiki, a Tokyo Michelin Bib Gourmand recommended restaurant that serves concept ramen. Konjiki’s chef Yamamoto chose Willowdale for the first North American location of his award-winning restaurant.

After dinner, grab your friends and head to one of Willowdale’s many karaoke spots. Rent a private room at Twister Karaoke.

The Communist's Daughter is as cozy and eclectic as they come

The Junction

The old-world charm of the Junction is left over from the area’s start as an intersection of indigenous trading routes. It was laid over by railway tracks, established as a village and became a city so wild it implemented an alcohol ban that lasted almost a century. Now, this neighbourhood is a craft-beer-lover’s dream with an exciting food scene.

The Junction’s Indie Alehouse offers adventurous, small-batch beers with a menu of out-there items to match. People’s Pint, Junction Craft Brewing, Rainhard and Shacklands all have a taproom and bottle shop so you can grab a pint or take your craft brews home for later enjoyment.

Go hunting for the Hole in the Wall – as the name implies, the door to this long, narrow bar is slightly hidden. Try anything from the ever-changing menu. On weekends, start your day at Honest Weight – they serve brunch with a seafood twist.

Playa Cabana Cantina is the place to go for tacos, tostadas and other Mexican dishes. For more stylish dining, head to Roux for seafood and southern fare – get the jambalaya or pan-roasted catfish. After dinner, catch a show (everything from alt-`rock to country) and a round on the pinball machines at Junction
City Music Hall.

Yorkville

While Toronto’s classiest neighbourhood may be known for its designer boutiques and the Lamborghinis that cruise its tree-lined streets, Yorkville was once the most swinging part of the city. Back in the 1960s, the area was a haven for writers and musicians. Joni Mitchell, Gordon Lightfoot and Neil Young all played in smoky coffee houses inside Victorian row houses on Yorkville Avenue.

Nowadays, refined dining is Yorkville’s meal du jour, with Cafe Boulud, Buca, Chabrol and Joso’s heading up the vanguard. (Relative) newcomers, Sofia, with its bright Italian small-plates, and Brothers Food and Wine, a tiny Mediterranean spot directly above Bay Station, continue the upscale tradition.

Grab a scoop of Campfire Marshmallow at Summer’s Ice Cream and stroll down Old York Lane, a Parisian-looking alley. Once on Cumberland, hit up Yorkville staple Hemingway’s, a Kiwi-owned pub with a year-round patio that’s been pulling in pint drinkers for decades.

For a rooftop spot with history, head to Pilot’s patio, Flight Deck, named in honour of the heroic RCAF flyers. Originally located on Yonge, the venue counted Bob Dylan among its clientele, before moving to its current home.