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They can fine you. Not worth it. They patrol it pretty hard. If you hike, you're very exposed, so it is likely they will track you down at some point. That, or they'll just ask in the park.
This summer there should be plenty of snow for jibs and jumps outside of the Timberline boundaries. If I understood this thread right, you want to bring a rail up and set it up somewhere?
If that's the case, just park at the T-Line parking lot and scope the canyon to the east.