Go Portland. But… other cities/states will struggle for 1/2 the year since many many months are quite cold for biking (and snow and such) so it’s hard/dangerous to bike. How Bikes Make Cities Cool – Portland If one is riding to work/school at 8 am it is very cold in MA even in October. Seasonal temp avgs at wunderground.com if you are wondering. And then in the milder/hot months, you’ll need to shower a lot… at work, school, etc. Which is fine if there is a shower.
Geneva, Switzerland was also great for biking year round.
Dumb places we people live.