While the signs are short on details, they reference the municipal code which provides a more thorough description. Seems like similar problems to motorcycle mufflers where some bureaucrat with no experience in the real world banned hollywood mufflers. It seems like magive carpets, magic saucers, fast food trays, inner tubes, etc all escape the grasp of the by-law.
§ 608-22. Skiing, tobogganing and sledding. While in a park, no person shall:
A. Ski, toboggan, snowboard, skibob or sled in an area in a park where it is posted to prohibit it;
orB. Fasten or attach a ski, toboggan, snowboard, skibob or sled to any vehicle, motorized vehicle or motorized recreational vehicle for the purpose of being towed, dragged or otherwise pulled.
In other interesting news, Citynews interviewed city staff and not a single person ever has been given a tobogganing ticket. So you have a toboggan hill inspection program with tons of staff time allocated, you have signs made up for 45 hills with tons of money required to do that and you never ever enforce the by-law? That seems like an easy win in court where they can show that the city was pretending and the by-law has no force. How many people go tobogganing on closed hills in the city every year? Probably tens of thousands. And zero tickets. That would be a very hard win for the city and they would be covered in mud and eggs. It's hard to tell quickly, but it looks like that wording has existed for 20 years with tens of thousands of violations a year with zero tickets. Sounds like a by-law that should be repealed as inactive rather than wasting money on signs.