The official smoke on the mountain run is traditionally at the end of october. It sounds like Bob V is going to take it back over this year, as his kids sports activities will not interfere as they have the last couple years that I have organized it.
Bob has talked of doing a trip to the backside of st helens, but last I heard, that road got wiped out, and has not been repaired. Its also supposed to be a dirt road, and minimal facilities at the top.
There is a serious lack of event planners out there. Its a challenge, but when the event goes smoothly, it is its own reward. Keep it simple, and dont make any plans by committee/vote and you'll be fine. Ive found that the "benevolent dictator" approach has given me the best results to date.
Dont be afraid to just throw something out there that intrests you, and make it an open invitation. Thats pretty much how the smoke on the mountain run started. Just a handful of trucks to the top of the hill. Now its darn near a major event!