Finally realized the best place to look for a toboggan listed online would be somewhere here in NC, so tada! found one. If you happen to be in North Carolina (not sure about the rest of the south), then
this is a classic example of a toboggan!
They can either be exactly like that and worn snug, or oversized and flopping around a bit on the top, some cutsey ones will have those annoying balls on top, etc. The main requirement is its a knit-type hat like that. And before my story in the previous post, i seriously had no idea there was anything else called a toboggan or that this was a regional thing.
Here, that wooden sled above is simply that, a wooden sled.
Also, I almost forgot, its often shortened to 'boggan in casual conversation.