The writers of skating history have awarded Jackson Haines credit for inventing the toe pick in the nineteenth century. They must not have known about the prikschaats (prick-skate). This type of skate features an iron blade with a spike at the toe. It’s not quite like a modern toe pick, being a single spike rather than a set of small teeth, but it’s definitely along those lines.
The prikschaats dates to around 1300–1500. Two have been found so far, one in the Hague and one in Rotterdam. It’s also featured in the manuscript image I described in a previous post, and, if you look carefully, one of Lydwina’s companions might be wearing one in the picture of her accident.
Modern toe picks are for jumping. It’s considered bad form to use them to stop in figure skating (which only works if you’re going backwards anyway), and only beginners use them to push (“toe-pushing” is trained out of beginning skaters early on). I’m not convinced that people were jumping in the Middle Ages. I think it probably represents the shift from pole-pushing to foot-pushing. When they used bone skates, skaters had to push themselves along with a pole. The earliest metal-bladed skates don’t have toe picks, and Niko Mulder has argued that they were propelled with a pole, just like bone skates.
The picture in Douce 5, the manuscript from my earlier post, shows someone skating without a pole, but with prikschaatsen. Maybe early skaters decided to move the point from the pole to the skate so that they could push with their toes. Eventually, they learned that pushing from the side of the blade works even better.
Niko Mulder. 2008. Ten IJse (2)—Schaatsles voor graaf Floris. Kouwe Drukte 12.34:18–23.