US and Canada’s Coolest Cities

Sophie Bryant
Written by: Sophie Bryant Fact checked by: Chris Altman
Last Updated:

Most people want to live somewhere that’s considered cool. After all, being a resident of a cool city surely means that you’ll have access to a wider range of activities, opportunities, experiences and conversations. But what exactly makes a city cool, and how do you go about deciding its level of coolness? 

An image of Toronto downtown with the words "US and Canada's Coolest Cities" overlayed on top.

To identify the coolest cities in the US and Canada, Canada Sports Betting analyzed 50 of the most populous cities using eight key categories:

  • Cultural and Arts Scene
  • Lifestyle and Recreation
  • Population/Residents
  • Dining and Nightlife
  • Social and Community Engagement
  • Tech and Connectivity
  • Environmental Sustainability
  • Trendiness and Media Coverage

We assessed these categories using 19 relevant metrics and created an index with a top score of 100 (our full methodology can be found at the bottom of this article). The higher the score, the cooler the city. Now that you know the science behind the project, let’s take a look at the US and Canada’s coolest cities and why they’re considered a hip place to be.

What Makes a City Cool?

The eight categories we used cover the many aspects of a city and what goes into creating its overall vibe. The cultural and arts scene of a place, for instance, gives a flavor of what locals can experience on their doorsteps, from live music events to museums and places of historical importance.

Meanwhile, lifestyle and recreation cover all kinds of enjoyable everyday activities, such as attending a sports event, taking a shopping trip, or simply enjoying a mindful walk in a public park. When all eight categories listed above are combined, from a city’s tech scene and connectivity levels to its environmental policies, social inclusion and general media coverage, we can measure how cool it is. While the largest cities such as NYC and LA are the most obvious, there are others that have made our list due to their unique personality and universal attraction.

When carrying out this research, some of the categories had a greater influence than others. For example, Google searches are weighted low while the number of historical places is weighted high, as this gives a fairer and more tangible representation of the city in question.

Now, let’s see which cities made the top 10!

The Top 5 Coolest Cities in the US and Canada

1. New York City

It may come as no surprise that the Big Apple ranks as the number one coolest city in the US and Canada. New York City gained its place at the top of the rankings due to its global influence, being the number one most Instagrammed city on the list, due to its iconic skyline and impressive number of historical landmarks (803). The city is also recognized as the most innovative city out the 50, as well as being a hub for music and arts (4,872 upcoming music events). NYC also has a lot of upcoming sports events (737 in total), giving fans the opportunity to see some legendary sports teams such as the Yankees or the Knicks, boosting their score in the ranking. NYC receives a coolness score of 72.68 out of 100.

2. Washington D.C

Coming in second place, with a coolness score of 48.75, is Washington D.C. Known for its rich history and iconic monuments, D.C. is home to 116 museums and 652 historical places of importance. It also boasts a thriving food and arts scene, with 120 restaurants being identified on the Michelin Guide and over 1,500 music events coming up over the next 12 months.

Washington D.C. also scores highly for metrics related to green space, receiving the third best Green City Index Score (68.2/100) and having the highest percentage of National Parks, in relation to the city. Not to mention, D.C. is also home to several major league powerhouses such as the Nationals, Capitals, Commanders and more.

3. Los Angeles

Rounding off the top three is Los Angeles, which received a coolness score of 48.66/100. The city people flock to in order to make their dreams of stardom come true, LA’s coolness factor comes from its mix of entertainment (4,440 upcoming music events), innovation (ranks as the second most innovative city) and its unmatched lifestyle, which is often broadcasted across social media.

Similar to NYC, LA also ranks high for sports events, having over 500 coming up over the next 12 months, providing sport fans with an opportunity to experience the NFL, NBA, MLB, NHL, MLS and more.

4. San Francisco

Receiving a coolness score of 44.63 out of 100, San Francisco’s cool factor lies in its mix of tech innovation (the second highest on our ranking behind NYC), historical landmarks such as the Golden Gate Bridge, and impressive sports teams such as the San Francisco 49ers.

It is also home to world class food with 167 restaurants on the Michelin Guide, a vibrant music scene (2,540 upcoming events) and plenty of green space. In fact, San Francisco has the third highest percentage of city which is made up of parks/green space, across the top 50 cities.

5. Portland

Closing off the top 5 is Portland, which achieved a coolness score of 42.26 out of 100. Known for its relaxed vibe and commitment to green initiatives, Portland ranks high on several factors, such as the Green City Index Score (68.79/100) and the number of historical places across the city (619). Also, home to a strong craft beer and coffee culture, Portland has the most micro-breweries (188) of any city in the ranking and has over 460 coffee shops on offer.

There are also plenty of upcoming sport events in the city, with the Portland Trail Blazers, Portland Timbers and the NWSL’s Portland Thorns FC calling the city home.

Toronto Makes the Top 10

6. Toronto

Canada now enters the list, with Toronto, Ontario at number six with a score of 40.94 out of 100.

Toronto’s cool factor comes from several metrics, such as its food scene, downtown city vibe and active music and arts set up. Diving into our ranking, Toronto ranks second highest in the ‘Dining and Lifestyle’ metric, with it being home to a significant amount of coffee shops and having 78 restaurants on the Michelin Guide. The city also performed well for ‘Tech and Creativity’, having one of the highest innovation scores (52/100) and being a hub for startups; there are currently over 14,000 in the city.
Like many of the cities in the top 10, Toronto is also a fantastic location to catch a sports fixture, with over 218 events coming up over the next 12 months and teams such as the Toronto Raptors, Toronto Maple Leafs, and Toronto Blue Jays performing at the highest level.

Canada’s Top 10 Coolest Cities

Only one Canadian city made the top ten, with Toronto doing the country proud. Now let’s take a look at the ten coolest cities in Canada, where they placed in our overall list, and their scores.

  1. Toronto: Coolness score of 40.94 out of 100 (#6 in North America)
  2. Vancouver: Coolness score of 33.25 out of 100 (#13 in North America)
  3. Calgary: Coolness score of 27.71 out of 100 (#18 in North America)
  4. Montreal: Coolness score of 25.48 out of 100 (#21 in North America)
  5. Edmonton: Coolness score of 24.97 out of 100 (#24 in North America)
  6. Winnipeg: Coolness score of 20.79 out of 100 (#35 in North America)
  7. Ottawa: Coolness score of 19.92 out of 100 (#40 in North America)
  8. Quebec City: Coolness score of 15.68 out of 100 (#45 in North America)
  9. Kitchener: Coolness score of 15.61 out of 100 (#46 in North America)
  10. Hamilton: Coolness score of 14.91 out of 100 (#48 in North America)

There you have it, Canada’s top 10 coolest cities, all of which made the top 50 list of the coolest cities in the US and Canada.

Do You Live in a Top 10 Coolest City?

How do you feel about these numbers? Do you think more Canadian cities should have made the top ten? Or perhaps you’re adamant that Montreal is cooler than Toronto? Whatever the case, if you live in Toronto, Vancouver, Calgary, Montreal, Edmonton, Winnipeg, Ottawa, Quebec City, Kitchener or Hamilton, you now know that you’re a resident of one of the top 50 coolest cities in the US and Canada.

Has this research got you excited for live sports events? Check out our best sports betting sites if you’re keen to get in on the action!

Methodology

To identify the coolest cities in the US and Canada, Canada Sports Betting analyzed 50 of the most populous cities across eight key dimensions:

  • Cultural and Arts Scene
  • Lifestyle and Recreation
  • Population
  • Dining and Nightlife
  • Social and Community Engagement
  • Tech and Connectivity
  • Environmental Sustainability
  • Trendiness and Media Coverage

We assessed these dimensions using 19 relevant metrics, detailed below with their assigned weights. Each metric was rated on a 100-point scale, where a score of 100 denotes the highest level of coolness.

To determine the overall ranking, we calculated each city’s weighted average across all metrics and summed these scores to produce a final indexed score.

Key:
Increased Weight = 7.89%
Full Weight = 5.26%
Half Weight = 2.63%

  1. Cultural and Arts Scene
    • Median Age (2.63%) – The average age of the city (AreaVibes).
    • City Population Growth (2.63%) – The percentage growth of the
      city’s population since 2001 (TPL).
  2. Dining and Nightlife
    • (Micro)Breweries (7.89%) – The number of breweries in the city
      (Brewerydb).
    • Coffee Shops (7.89%) – The number of coffee shops in the city
      (AreaVibes).
    • Restaurants on Michelin Guide (5.26%) – The number of restaurants
      in the city which appear on the Michelin Guide (MichelinGuide).
  3. Lifestyle and Recreation
    • Upcoming Sports Events (7.89%) – The number of upcoming sports
      events in the city (SeatGeek), (Ticketmaster).
    • Thrift Shops (5.26%) – The total number of thrift shops in the city
      (TheThriftShopper).
    • Parks as % City Area (5.26%) – The percentage of the city which is
      made up of parks/green space (TPL), (ParkPeople).
  4. Population
    • Median Age (2.63%) – The average age of the city (AreaVibes).
    • City Population Growth (2.63%) – The percentage growth of the
      city’s population since 2001 (TPL).
  5. Social and Community Engagement
    • Volunteerism (5.26%) – The percentage of the city’s population who
      have volunteered during 2023 (AmeriCorps).
    • Nonprofits (5.26%) – The number of nonprofit businesses which
      operate out of the city (Crunchbase).
  6. Tech and Connectivity
    • Startups (5.26%) – The current number of startups in the city
      (Crunchbase).
    • Internet Speed and Connectivity (1.315%) – The median WIFI
      speeds across the city (Ookla).
  7. Environmental Sustainability
    • Green City Index Score (5.26%) – An index score of the greenest
      cities which includes 28 metrics (WalletHub).
  8. Trendiness and Media Coverage
    • Instagram Hashtags (2.63%) – The number of Instagram posts with
      the hashtag of the city mentioned (Instagram).
    • Google Searches (1.315%) – Average monthly search volume for the
      city on Google (Keyword Planner).