Orienteering is effectively banned in High Park. Not just orienteering, but any organized trail running. The Toronto high school cross country champs used to be held there, but not any longer. I understand that's thanks to the Friends of High P., some of whom don't even like it when anyone runs past them on a trail - they think runners should stay on the roads.
I obtained the last High Park permit as meet director / course setter for a "Why Just Run", which had a marked route on the map (that I had to get approved), but with shortcutting allowed. It was made clear to Don Ross (controller) and me that this would be the last time TOC would get a permit for High Park. We relayed that information when TOC proposed to hold another Why Just Run at High Park, but we were ignored. In addition to the event for which the permit being refused, TOC had a Wednesday training scheduled for the week after the proposed event - those are always done without permits. Park officials saw that training listed on the TOC website, and klepperton's uncle, who was the organizer that Wednesday, got a citation for putting on an event without a permit. After that High Park wasn't even used for Wednesday training for quite a few years. Last summer the organizer of the Wednesday trainings put on two of them at High Park, but in a particularly low key manner (he just sat on a bench at the edge of the park handing out free maps for about an hour).
Ralph: Was this my Uncle Pete or Uncle Dave?
Also, I think there is a way to build a relationship with 'Friends of High Park'.