The 10 coolest cities in North America

In the aftermath of the COVID-19 pandemic, many Americans have more control over where they live than ever before.

Policies that allow employees to work from home mean that the average American in 2023 lived 27 miles away from their employer — compared to 2019 when people lived an average of 10 miles away from work, according to a report from economists at Stanford and Gusto, a payroll provider.

With all this newfound flexibility, Americans can now prioritize other factors besides work when choosing where to live. While practical concerns – like the cost of living and available transportation – are often most relevant, there are also other more ephemeral qualities that come to mind when choosing where to reside.

Among those qualities is “coolness” — a trait which is admittedly hard to define. A recent analysis from Canada Sports Betting, a gambling app, conducted an analysis on the relative coolness of North American cities based on eight categories, including cultural and arts scenes, dining, nightlife, and recreation.

“When all eight categories 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,” the analysis explained. “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.”

The analysis reviewed 50 of the most populous cities in North America, though Toronto was the only Canadian city to make the top 10 list.

One of the metrics included in the lifestyle and recreation category was upcoming sporting events, which Canada Sports Betting has a vested financial interest in promoting as cool. Notably, however, the list did not specifically take into account the number of casinos or the legality of gambling in the ranked cities.

Continue reading to learn more about the 10 coolest cities in North America, according to Canada Sports Betting’s analysis.

10. Philadelphia

Photo: Joe Daniel Price (iStock by Getty Images)

9. Boston