I think we found us a sweet spot for the main summer run, that weekend leading into the 4th of July week - it was NOT crowded and the weather was excellent. Tents are always cheap, but the fall weather makes that sorta thing iffy with cold and rain being a lot more likely then. Takes 5-6 to make the apartment work out to $25 a head. Takes 3-4 people to make a standard hotel room come out cheap. Labor day is still hot weather, ain't no cold around Labor day but I bet the place is booked up already. Monday, September 7th (Labor day) is the only standard 3 day weekend holiday to plan around in September. Is there a fall break for teachers? If so, when is it? We had 3 teachers there this time. Next, since so many of us are retired or not working, maybe hitting Monday Tues Weds might make things work out better since I suspect all the early fall and all the leaf season weekends are already booked up at the Gap. Leaf season is crazy up there (and getting too cold to ride comfortably too) so I would suggest hitting some date that is kinda early to the leaf season, when it is still more warm than cold. You need a date that folks can plan around and enough lead time for folks to hit that mark.