the hat Milo describes is a Ski Hat in NY-- and comes with either one slit/hole for the face or one for eyes, one for nose and one for mouth.

a tobaggin is flat sled, that seats 3 or more people, with a curved front --(a regular sled, is a flat surface(open boards, usually raised on metal runners, (the runners are shaped almost like bladed of the blade of figure (ice) skates) --radio flyer (them of little red wagon fame) also make sleds. (or see a sled in the closing minutes of citizen kane, when the flash back shows kane, as child getting a sled for christmas.. (rosebud)

sleds have moveable cross bars in front, with ropes attached, to help you stear the sled, and to pull it up the hill.
(and nowday, saucers are popular for snow.. round or oval or a rounded triangular shape, they are modern improved versions of garbage can lids--(ghetto sleds) )