Where in the midwest has the most mild days? (transplants, activities)
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I don't know for sure, but I'd guess the southern midwest (KCMO, St. Louis), as well as areas along some of the great lakes, like Holland, MI or Erie, PA. Of course, those areas get lots of snow, but you didn't ask about snow.
I'd wager it's going to be west coast Michigan, due to the way air patterns move. Humidity will be a little higher in summer and it will be marginally cloudier throughout the year than many other midwest areas, but the temperature will be milder for much of the year.
Away from bodies of water you'll have portions of the year where it's far hotter. Go south and winters are less cold but summers get similarly more hot.
I don't know for sure, but I'd guess the southern midwest (KCMO, St. Louis), as well as areas along some of the great lakes, like Holland, MI or Erie, PA. Of course, those areas get lots of snow, but you didn't ask about snow.
55-80F in KC and STL? Not too frequently, the only half decent season in those areas is Autumn. Summer is far too hot and humid with a brutal sun angle. Winter is generally either too windy/dry or some form of nasty mixed precipitation. Spring lasts a few weeks many years..
I think 95 is a pretty high bar for lousy weather. When you factor in humidity anything over 80-85 feels pretty lousy in my opinion.
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