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This topic can go all over the place as some of us like warm winters, some like cold winters, etc. And my opinion changes like the wind, but let's include things to do in the area as a factor:
Spring - DC. Warm enough and winters are still tough enough to where you appreciate spring.
Summer - Miami I'm not actually looking for warm to hot here, though admittedly 70 degrees in some parts of California can be glorious.
Fall - Chicago/NYC. Not too cold and you're coming off a pretty hot summer. Plenty of things to do.
Winter - Denver. Not blast you in your trousers cold, but cold enough and near the mountains.
I like having four seasons and to know which one I'm in without the extremes. I'm not too picky about cities.
Fall - Albuquerque -- September to Thanksgiving. Gorgeous weather, fall colors, Balloon Fiesta, laid back calm weather.
Winter - Somewhere on the Gulf Coast -- Florida Panhandle: Destin, St. George Island, Gulf Shores, etc. Warm but still you know it is winter. Maybe some crisp days.
Spring - a tough one for me as I'm not crazy about wind. Maybe in Colorado or New England or the Missouri/Arkansas Ozarks for April and May. Coastal California, maybe.
Summer - The high desert for low humidity and reasonable temps. I'd also like coastal North Carolina or Montana.
Winter -- Duluth. A dozen specles of boreal birds, who are otherwise never seen by humans. Usuallly fairly easy to see, at backyard feeders, and never learned to fear man. They funnel down to Duluth, because they don't like to fly over Lake Suprtior.
Winter- Southern California
Fall- Boston
Summer- NYC
Spring- DC
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