The best city breaks for Canadian travellers are easy to get to while also packed with possibilities. Naturally, many of Canada’s own big cities are on the list, as well as some across the border. What they each have in common is a wealth of attractions, whether that’s iconic sights or outstanding cultural scenes.

With Labour Day on the horizon in Canada, we have one last chance for a short getaway before temperatures start to drop. Don’t miss this great opportunity to enjoy a short-lived change of scene before the end of summer! Check out our guide to great destinations in Canada and the US for a long-weekend city break and start planning yours.

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    Montreal

    Quebec, Canada

    Montreal
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    Montreal is a beautiful historical city in Francophone Quebec. To this day, it almost feels more European than North American. Start your explorations at the beautiful Place d'Armes and make sure you visit Notre Dame Basilica, L’Oratoire Saint-Joseph, Bonsecours Market, and the City Hall.

    Mount Royal gives you a great view over the sky-scraping city centre and the Saint Lawrence River beyond it. Check out the Underground City, too – a network of about 32 km of tunnels that have been converted into a giant underground shopping mall.


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    Halifax

    Nova Scotia, Canada

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    Halifax is a seaside city that promises a great deal of family fun. It’s home to some excellent beaches, of course, as well as gorgeous gardens and an impressive number of museums and historical landmarks. Perhaps the most noteworthy of these is Citadel Hill, where you can learn about the region’s extensive military history.

    Another fascinating spot around the city is the Halifax Boardwalk, which offers historical spots, museums, and some outstanding restaurants and bars. Alternatively, head a little away from the water and into Downtown Halifax. It has big malls and markets, as well as dozens of cafés, that spill out onto the sidewalks.


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    Calgary

    Alberta, Canada

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    While Calgary may be better known for hosting the 1988 Winter Olympics, that certainly doesn’t discount it as a summer city break destination. It’s effectively the crossroads of Canada, sitting between the Great Plains and the foothills of the Canadian Rocky Mountains. It also sits at the confluence of the Bow and Elbow rivers and combines historical interest with contemporary culture, creating a real melting pot of a city.

    While the Calgary Tower dominates the skyline, the range of things to see and do in the city ranges from the tranquillity of Prince’s Island Park to the excitement of the Heritage Park Historical Village. Downtown Calgary also boasts an impressive array of restaurants, bars, shops and more.


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    Ottawa

    Ontario, Canada

    Ottawa
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    Ottawa is undoubtedly a cultural hub, alongside being the nation's capital. As with many of Canada's biggest and oldest cities, the streets are lined with an odd combination of historical and ultra-modern buildings – and sometimes both in the same place, as with the Canadian Museum of Nature. In total, there are 24 National Historic Sites in Ottawa, ranging from the Rideau Canal to the Parliament Buildings.

    There’s certainly no shortage of things to do in the capital, regardless of what interests you. There are 6 professional sports teams to watch, countless national museums to explore, regular festivals of all kinds, and huge numbers of great boutiques, theatres, galleries, cafés, bars, and nightclubs. Start at the city's cultural hub – ByWard Market – and see where your feet take you!


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    Charlottetown

    Prince Edward Island, Canada

    Charlottetown
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    Charlottetown may be the provincial capital of Prince Edward Island, but it retains a small-town feel. It’s a great place to get away from the bustle of the big cities and enjoy some peace in beautiful natural surroundings. Check out the various trails, water sports, and golf courses dotted around the city.

    If you looking for a more cultural city break? Check out the extensive selection of art centres, theatres, and historical sites. In particular, you should visit the Confederation Centre of the Arts, which focuses on the evolution of Canada as a nation through a range of art forms. Be sure to look up what events are being held as part of the Charlottetown Festival while you’re here, too.


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    Vancouver

    British Columbia, Canada

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    Vancouver is a remarkably diverse city that clings to the west coast, in the shadow of the Canadian Rockies. The choice of things to see and do is as diverse as the population and cuisine, with exciting wildlife encounters off the coast, beautiful scenery inland, and plenty of attractions in the city itself.

    Canada Place is a great place to start your exploration of Vancouver, with great shopping, dining, and entertainment options available right by the waterfront. After that, head to Canada’s largest Chinatown and end the day in the Granville Entertainment District, with its many cool bars, theatres, and nightclubs.


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    New York City

    New York, USA

    New York City
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    New York City is…well, it’s New York City! The Big Apple, the city that never sleeps and that’s so nice they named it twice – its world-spanning reputation makes description kind of redundant. It’s the home of Times Square, Broadway, the Statue of Liberty, Central Park, the Empire State Building – the list goes on and on and on. And on.

    Being such a big and bustling city, it's best to decide what you want to see and do in advance. It's quite a challenge to see everything in one go, least of all in a short summer city break. Whatever attractions you choose to focus on, you're almost guaranteed to have a memorable trip.


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    Chicago

    Illinois, USA

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    Being one of the biggest cities in the world, Chicago certainly has plenty to offer visitors from north of the border. Its standout landmarks include the impressive Millennium Park, the jolly Navy Pier, the iconic Willis Tower and more.

    If you’re looking more for things to do than places to see, Chicago will leave you no less spoilt for choice. Shop on the Magnificent Mile, dine on the famous Chicago-style deep-dish pizza, take in a show at the Chicago Theatre or listen to a staggering array of live music. Expect masterpieces performed by the Chicago Symphony Orchestra, as well as the best of Chicago blues, soul, jazz, house, hip hop, and alternative rock. And don’t forget Chicago’s many iconic sports teams, from MLB’s Cubs and White Sox to the NFL’s Bears, NBA’s Bulls and NFL’s Blackhawks.


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    Seattle

    Washington, USA

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    Seattle is famous for an odd combination of reasons. Located on Puget Sound, you can have wonderful wildlife encounters right from the beach. The city itself is famous for giving the world Starbucks coffee, Jimi Hendrix (and numerous other famous musicians) and the iconic Space Needle.

    There are numerous festivals to enjoy during Seattle’s summer, as well as a wealth of famous sights to discover. Be sure to check out the Pike Place Market and Seattle Great Wheel, though expect crowds at both. Fortunately, the city also has a great choice of lesser-known places to see, such as the Seattle Underground, the Fremont Troll, and Gas Works Park.


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    Nashville

    Tennessee, USA

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    While Nashville may be a long drive or flight for a quick city break from Canada, it's definitely worth the journey. The capital of Tennessee is famous for being the capital of country music, and it's a reputation it fully deserves. Must-visits include the Country Music Hall of Fame, the Grand Ole Opry House and dozens of honky-tonks in the District, Downtown and Music Row.

    If denim and line dancing aren’t your thing, Nashville also has a fair share of weird and wonderful sights. There’s a full-scale replica of the Parthenon in Centennial Park, the famous Frist Art Museum, and a few US Civil War sites.


Ben Reeves | Compulsive Traveler