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Seattle obviously the best winters on this list with plenty of rain, milder temperatures, and the least snow. New York is eh, Boston is bad, and all the others are just trash, being too dry and cold in winter, or in the case of Denver, average seeing snow in October/May, which is absolutely atrocious, not to mention the dryness. I know it’s an unpopular opinion, but Denver has crappy winters because of how variable they are as well as hardiness zone
I think Boston is more windy than Chicago, but oh well.
The least crappy winter would be in the city with the most snowdays, where it is also cold enough to sustain that snow for a reasonable amount of total days during the winter months. Also, a low amount of sunshine since that gives a nice cozy winter feeling. I don't know which city will win with these criteria combined, but I guess it's somewhere near the Great lakes.
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Anywhere in coastal California ( San Francisco , Santa Cruz , Santa Barbara ) is , for me , perfect
winter weather. And, summer , for that matter where the temps are rarely above 75 degrees.
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New York City for being among the milder winter climates of the bunch with Seattle being a runner up. Minneapolis probably has the worst winters of the bunch due to it having the most severe winters out of all of those cities IMHO.
I don’t know which has the best, but I’d say Seattle has the crappiest. There something so incredibly depressing about rain and 40 degree temps just about every day (at least that was what it was like when I spent the winter there). I’d rather have it a bit colder and a bit sunnier, with the occasional snowstorm.
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