Ok, here's mine:
Most similar to: Buffalo, Rochester, and Arlington (hmmm). Buffalo and Rochester are spot on - they're only like a 3 hour drive max from Toronto. And most of our American TV stations are from there. In fact, pretty much all of NY is super red on my map.
Least similar to: Philadelphia, Houston, and Detroit (kind of funny since I was born there. Didn't grow up in the Windsor/Detroit area though - they have their own accent down there.)