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They're both large cities on the northern end of the west and east coasts, and on similar latitudes (40'N/45'N), except their climates are still rather different. Which do you prefer?
I choose NYC because it is overall more interesting with colder, snowier winters and warmer summers, but Portland still has one of the better oceanic climates, quite similar to central western France, just with that distinct precip pattern.
I've lived in both. Portland may have cooler summers but don't be deceived by the averages. It gets frequent heatwaves that go well into the upper 90's and low 100's. It has low humidity so the temps tend to rise very fast when the air flow is from the east. You however only feel the heat during the day because as soon as the sun goes down, it cools down quickly, which never happens in NY.
Winter in PDX is milder but also very rainy and gloomy. The rain is rarely very heavy but is generally drizzly and misty. It can last for days. It does get cold, too. The same air flow from the east through the gorge during winter can bring in very cold windy air.
For me, it's a toss up. They both have good and bad.
The good PDX:
- milder winter with less snow
- low humidity during the summer
The bad PDX:
- chilly, dreary, rainy winters
- summer kind of short and doesn't feel like it with the cool nights (if you like summer, it is disappointing)
- still get cold and snow, just not as much.
NY good:
- Sunnier for most of the year
- true summer
NY bad:
- colder and snowier winters
- humid summers
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