The first one, an Indian (or if you prefer, Native American), with reddish skin and a bow and arrow for hunting. So far so good.
But then, a rather shocking portrayal of a Puritan. Since when does a Puritan wear a kippah, tzitzis, and hold a sefer? While I can understand the urge to remake the Avos in the mold of modern Jews; and while I can somewhat understand wanting the children to identify with the first new American settlers, surely the Puritans weren't Orthodox Jews! Wouldn't this just confuse them? What were his teachers thinking?
Then, the answer -- this wasn't supposed to be a portrayal of Indians and Pilgrims. It was his parshas Toldos project, and it was Esav and Yaakov! (Indeed, see Esav's body hair.)
The initial reaction was not my own, but rather someone else's. Still, it was understandable based on the context, in that it was among many Thanksgiving projects.
Of course, there are still other anachronisms here, but these are more common ones, and not as bothersome. Did Yaakov Avinu actually wear a yarmulke, tzitzis, and learn from a bound sefer written in ksav ashuris?! Well, maybe according to the popular position from Chazal, that the avos kept the entire Torah.
But would Yaakov have worn a kippah? That we know, since the pasuk says Vayeitzei Yaakov, and surely Yaakov would not have traveled 4 amos without his yarmulkah. (On the other hand, since it was kefitzas haderech, perhaps his actual strides did not amount to four amos...) Would he have worn tzitzis? Perhaps we can argue it, as it was the practice of the elite in those times to have something akin to this (techeiles on the edge of their garment). And the sefer? Well, what else would he be learning in the yeshiva of Shem and Ever? Although this type of book, rather than scroll, seems to have been a fairly late invention. And we would expect Paleo-Hebrew rather than ksav ashuris.