Growing up in Virginia, a "toboggan" was a knit hat. Only when I left the nest did I find out that to most people, a toboggan is a sled. A little googling revealed a discussion about this very discrepancy.

How very bizarre that this relatively long, unique word can mean two very different things! I'd like the linguists to explain this one.

A Google image search illustrates the double meaning as 95% of pictures show a sled and the remainder, a knit hat.

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A lot of the ones showing a

A lot of the ones showing a sled also show a knit hat (worn by the person on the sled).

I wonder if it's possible that a long time ago, a nationally published picture dictionary illustrated the word "toboggan" with a picture of somebody riding a sled wearing a knit cap, and the picture was interpreted in different ways in different parts of the country, some thinking "toboggan" referred to the sled and others thinking "toboggan" referred to the cap.

I'm not serious. But the thought springs to mind.

I grew up in Baltimore

and a "toboggan" meant a sled. Specifically a flat sled with a curved front edge that wrapped around and provided an edge for the rider to hold on to. A flat sled with a 'C' on the front. I never heard of the word used for a hat. We called them ski hats or knit hats.

"long, flat-bottomed sled,"

"long, flat-bottomed sled," 1829, from Canadian Fr. tabagane, from Algonquian (probably Micmac) tobakun "a sled." The verb is recorded from 1846. As Amer.Eng. colloquial for a type of long woolen cap, it is recorded from 1929 (earlier toboggan cap, 1928), presumably because one wore such a cap while tobogganing.

From the Online Etymology Dictionary, which is pretty good for these kind of questions.

In New Jersey, we never used either word. A toboggan was "a sled" and a
"knit hat" or whatever was "a hat," to be contrasted with a "baseball hat" or "cowboy hat." Soda was "soda," Bruce Springsteen was "awesome," and everybody said "hooking up" even though no one knew exactly what it meant.