By the sounds of it there will be several riding up Haleakala in Nov, it would be good to hear how they went while we're shivering in Seattle.

Regarding riding back to Wailea: If you ride down stay on the Haleakala highway, its down hill almost all the way to the airport, take the highway back into Kahului (cyclists generallly avoid Hansen rd due to roughness of road and trucks driving fast and no shoulder). Then go south after riding through town on sr 350 (most of it is a trail on the east side, and then take the Piialani hwy to Wailea (better than going through Kihei rd), would be a long day and most would be downhill or tailwind (trade winds, not sure how they are in Nov)

Regarding the short cut to Makena, everyone says there is no short cut, if there was it would be crossing private ranch land.