Growing up as a west coaster we didn't know what Winter Break was either. For the longest time I just thought that it was anothe rname for Christmas break (and these days it is). We didn't have it when I lived in Michigan or here in Maryland. Just the initial Monday off for President's Day. If you're luck you might get the friday off too making it a 4 day weekend.
Same here -- I grew up in Wisconsin and live in Illinois. We have Christmas break and then nothing til spring break (last week of March) - we did have a couple random days off, but that's it. Never heard of winter break until I started to DIS. Maybe that's why schools get out so late on the east coast? You get a break in Feb and again in April?
What's a Winter Break?
Seriously, I remember being in about 2d grade and reading a story in my English class in which the kids were on Winter Break. We all started asking our teacher about it and she had never heard of it, either. That was in 1968, I think, but I've still never personally encountered a school system that did it, and I've lived in the lower Midwest for 20 years now.
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