A delightfully eclectic collection of shops, eateries and Victorian houses converted into apartments, Kensington Market is the heart of old-school bohemian Toronto. Locals and tourists alike flock to its open air stalls for groceries and vintage clothes, or for world-class people watching over a coffee and casual bite to eat. The area has an artsy, hippie vibe and is packed with treasures to uncover and unique characters to meet.

Touted as Calgary’s oldest neighbourhood, Inglewood is a mash-up of heritage buildings, independent shops and restaurants, park spaces and cool art experiences. Located just east of downtown Calgary at the confluence of the Bow and Elbow Rivers, the neighbourhood was established in 1875. Today it is home to a number of music venues, the impressive Esker Foundation art gallery and several prestigious local restaurants, including Rouge and Deane House.

Vancouver’s oldest neighbourhood is also one of its best. Gastown’s origins date back to 1867, and the area got its name from the neighbourhood’s original tavern, founded by John 'Gassy Jack' Deighton. The main landmark is a fully operational steam clock, but modern Gastown’s big draw is its streets lined with cool restaurants, bookstores, boutiques and bars. It’s also adjacent to Vancouver’s Chinatown, another key West Coast neighbourhood. 

Known as 'the Paris of the prairies', much of Saskatoon is pretty darn cool, but inner-city Riversdale is a particularly vibrant part of the city. Here you’ll find picturesque heritage buildings, murals and other pieces of public art, alongside some of the city’s best restaurants and bars. Renowned local chef Christie Peters recently opened her Pop Wine Bar in Riversdale and visitors can also eat at trendy spots like the Odd Couple restaurant, or grab a beer at the 9 Mile Legacy nanobrewery.

Situated on the Lachine Canal, Saint-Henri has a long history of nurturing artisanal shops and other interesting businesses. Historic buildings and monuments abound, but lively Saint-Henri is very much up to the minute, full of modern buildings and trendy restaurants. One of the area’s best-known gems is the Atwater Market, one of Montreal’s biggest farmers’ markets, in addition to a high street lined with some of the most exciting eateries in the city’s world-famous dining scene.

Since so much of Canada is shiny and new, those seeking something different often gravitate to neighbourhoods like Winnipeg’s Exchange District, which is stacked with beautiful old buildings built between the 1880s and 1920s. The area is a joy to walk through for the architecture alone, much of which now houses creative business offices, arts studios and acclaimed restaurants. An arts hub, the district also comes complete with a wide array of theatres, museums and festival spaces.

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Just north of Halifax’s tourist-heavy downtown zone, the North End is where Haligonians go to eat at a diverse range of restaurants, see live music and take in eye-opening street art. Also rich in history, the area is the site of the former community of Africville, a Black neighbourhood that was torn down in the 1960s. The North End is set to recognise that history with an art piece honouring civil rights activist Viola Desmond, to be unveiled on Gottingen Street later this year.

This inner-city Edmonton neighbourhood feels like a small town, which is natural because Strathcona was once its own municipality before it was absorbed by the city in the 1910s. Old Strathcona’s Whyte Avenue is the heart of Edmonton’s hipster culture, with boutiques, bars, coffee shops and restaurants running up and down the street. Old Strathcona also hosts Edmonton’s world-renowned Fringe Festival every year.

Adjacent to the walled-in city of Old Quebec, Saint-Jean-Baptiste started life as a working class neighbourhood for 17th-century craftsmen. The modern neighbourhood retains that old world charm, boasting J.A. Moisan, the oldest grocery store in North America, and a number of vintage shops, microbreweries and restaurants. The wide sidewalks make the neighbourhood very walkable, and the main street is closed to vehicles on summer weekends.

BC’s capital city of Victoria is known for its British influences, but a different cultural experience lies just a short walk from the city’s famous harbourfront. Founded more than 150 years ago, this is the oldest Chinatown in Canada and the second oldest in North America. Heralded by the ornate Gate of Harmonious Interest, the businesses within Chinatown are diverse, with record stores, coffee shops and, of course, restaurants.

Whitehorse is widely considered the most bohemian city in the Canadian north, as exhibited by its quirky downtown neighbourhood. The city is surrounded by photogenic wilderness, while in the heart of town you’ll find a glut of Gold Rush history and First Nations culture, plus a Main Street full of cool wooden façades, art galleries and restaurants serving local fish and other Yukon delicacies.

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Westboro Village has roots that go back to the 1800s, but the neighbourhood has undergone a facelift in the last 20 years thanks to an influx of modern stores that have transformed it into a major commercial zone. The district is also known for bakeries and food trucks, and residents and visitors can enjoy the Ottawa River from a spot on sandy Westboro Beach or relax in the area’s ample green spaces.

The hub of BC’s wine country, Kelowna is mostly known for the wineries that punctuate its suburbs. But visitors shouldn’t ignore the city’s quaint downtown, made all the more compelling by a boardwalk that runs along the waters of Okanagan Lake. It’s a lively place in summer, with beach volleyball, live concerts, car shows and other entertainment, but downtowners can also frequent more permanent fixtures, including a collection of independent restaurants that showcase the wineries' produce.

Among Toronto’s greatest charms are its streets lined with Victorian-style brick houses, and many of the prettiest reside in The Annex, one of the city’s oldest neighbourhoods. Close to the University of Toronto and right on the subway line, The Annex has a youthful feel to it, with cool coffee shops and casual restaurants supporting landmarks like the legendary Lee’s Palace music venue and the Hot Docs cinema. If those aren’t of interest, strolling the residential streets is entertainment enough.

Montreal is probably Canada’s coolest city, and arguably none of its neighbourhoods are cooler than laid-back Villeray. With its roster of parks (including the activity-filled Jarry Park) and pedestrian-friendly streets, you’re bound to run into interesting Montrealers enjoying themselves outdoors all over the neighbourhood. The café, restaurant and bar culture is unparalleled, and Villeray is well-situated within the city, bordering the famous Jean Talon Market.

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The capital of New Brunswick is relatively small, but it packs a strong cultural punch. The city is known as the 'craft brewing capital of Atlantic Canada' and while there are breweries to be found throughout the city, the best place to start is downtown. Most downtown bars and restaurants have a good selection of local brews, with The Joyce serving as a hub for local beer.

Queen Street West is one of Toronto’s most famous streets, but you have to get past the ultra-commercialised stretch just west of downtown to get to the heart of its cool cred. From the intersection of Bathurst Street onward towards Dufferin Street, you’ll find highlights like the hip Drake Hotel, independent clothing shops and countless restaurants and bars. The jewel of West Queen West is Trinity Bellwoods Park, a popular outdoor hangout that stretches northwards towards Dundas West.

While it’s technically a road and not a neighbourhood, George Street in St. John's is an entity unto itself. The centre of the city's nightlife scene, George Street is lined with more than two dozen pubs, bars and music venues, all offering a hefty dose of East Coast hospitality. Anyone who wants to participate in the Newfoundland tradition of being 'screeched in' should head to George Street and find a cod to kiss.

Calgary's Kensington Village is a business district adjacent to the residential neighbourhoods of Hillhurst and Sunnyside. Between its 250-plus businesses and laid-back locals, Kensington has long been a popular spot for people from all over the city looking for a coffee, meal or shopping trip. The area’s Plaza Theatre was recently reopened and revitalised to serve as a cornerstone for the busy riverside neighbourhood, which also features a large park on its north side.

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A family-friendly neighbourhood just south of downtown Ottawa, The Glebe is one of the most desirable places to live in Canada’s capital. Built on land originally owned by the Presbyterian Church, it’s a comfortable neighbourhood bordered by the Rideau Canal and full of leafy trees. While it’s not known for wild nightlife, The Glebe’s commercial areas are full of nice bars, restaurants and locally owned shops.

A working class neighbourhood until relatively recently, Fraserhood's cultural diversity is best reflected in its vibrant restaurant community, with pho eateries, fancy pizza places, pasta joints (including the much-vaunted Pizzeria Barbella), taquerias and coffee roasters. Since this is beautiful Vancouver, expect outdoor elements like parks and mountain views.

Celebrated for its 19th-century brick homes and relaxed vibe, this neighbourhood just west of the city centre is one of Winnipeg’s oldest. A mix of hippie and hipster, West Broadway is the place to seek out cool spots like Thom Bargen coffee shop and Langside Grocery cocktail bar, as well as vegan restaurants and other eateries. It’s also the site of the annual Sherbrook Street Festival, a celebration of community and arts.

Another neighbourhood that started life as an independent town, Dundas has been part of the amalgamated Hamilton since 2001. It still retains its own sense of character, with a picturesque, historic downtown and easy access to nature. A stroll through town is improved by a coffee or a pastry and there’s plenty to be found, with a range of dining options to fuel you before a quick jaunt to nearby Webster Falls.

The ByWard Market is not only a functioning market and tourist attraction, it’s also a thriving community. Just a short walk from Parliament Hill, the market square is one of the oldest farmers’ markets in Canada, and the surrounding area has developed into a bustling district full of restaurants and entertainment venues. There’s always something to see, even if it’s just other people shopping and enjoying themselves.

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A neighbourhood within a neighbourhood, Hydrostone is technically part of Halifax’s North End, but this little strip has a flavour of its own. Constructed in the aftermath of the devastating Halifax Explosion of 1917, the neighbourhood was designed to resemble an English-style garden suburb. The ensuing architecture is what makes Hydrostone so magical, along with the curated European-style shopping options, offbeat eateries and art galleries.

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A former small town subsumed by the border city of Windsor, Walkerville was originally built as a pet project by Hiram Walker, owner of Canadian Club Whisky. Walker’s careful planning resulted in a well-executed neighbourhood, which is now filled with one-of-a-kind retailers and businesses. The area is an architecture lover’s dream, with preserved storefronts and pristine residential homes.

White Rock is a municipality in the greater Vancouver area, known for its holiday-town feel. Sitting on Semiahmoo Bay, the area is named after a literal white boulder that sits proudly on the beach. Visitors can wander the seaside promenade, duck into shops for snacks or ice cream, check out works by local artisans or get out onto the bay via the famous White Rock Pier.

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Toronto is Canada’s largest city, but residents can enjoy some serenity east of downtown in The Beaches. Named after four actual sandy beaches on Lake Ontario, the tight-knit residential neighbourhood is slower-paced than other parts of the city, and people of all ages can be seen roaming the commercial streets, swimming in the lake or spotting wild birds. The neighbourhood also attracts artists and hosts the annual Beaches International Jazz Festival.

The town of Tofino is so small that it's all one neighbourhood, and definitely among the most intriguing communities on Vancouver Island. It's part surfer hangout, part foodie holiday spot and part natural wonder – all seemingly a world away from the rest of Canada. Time moves slowly in Tofino, whether you're tramping through ancient forest or gliding between islets in a kayak.

In a city filled with artists, Mile End stands out for being particularly high on artistic flair. Galleries and artist collectives are scattered throughout the neighbourhood with plenty of elegant restaurants and vegan eateries to keep the energy flowing. Shopping is also a major Mile End draw, with a host of home design stores, book shops (including Drawn and Quarterly, famous for publishing cartoons) and vintage retailers to complement the aesthetic of the neighbourhood.

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