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A pokey grey caterpillar
My farm
Here in Dutchess County, NY (Hudson River Valley), the locals call these "woolly bears," and they predict weather by them. If there is more black than brown, we will have a harder winter, so they say. I found one last week.
I believe the smaller of the two could be a Gypsy Moth caterpillar (Lymantria dispar), however, they aren't normally seen this time of year.