It won't take you days to drive the Skyline Drive unless you stop and hike a lot. The Skyline Drive ends in Waynesboro (which is south of Massanutten/Harrisonburg), at which point the Blue Ridge Parkway starts. (Honestly, you won't be able to tell any difference in the roads going from one to another.) The Blue Ridge Parkway is free whereas you have to pay to drive on the Skyline Drive since it is a National Park. The Skyline drive is about 100 miles long, but personally, I'd take the southern route and head towards the Blue Ridge Parkway. Crabtree Falls is actually off the the Blue Ridge Parkway. As the previous poster said, it is beautiful. Another hike that people like is Humpback Rocks which is also on the Blue Ridge Parkway.
About an hour from Massanutten in Monticello, Thomas Jefferson's home. They've done a lot of restoration work there and I think it's worth a visit if you've not seen it before. I don't know how much the admission price is, but I'm guessing around $20.
I love Luray Caverns, so to me that would be a definite must! If you've heard of an artist named P. Buckley Moss, she has a museum in Waynesboro which her fans like.
Most restaurants I know in the Harrisonburg area are more of the chain type restaurants - Red Lobster, Chili's, Applebees, etc. If you're really hungry and don't mind buffets, you might want to try the Wood Grille Buffet. Lots of variety! I'm not sure what the restaurant options are in Massanutten, although I'm sure they have some.