Both are really nice drives, but I'd definitely recommend driving north on Skyline Drive - even though you have to pay a national park entry fee, which is something like $10-15 for a car, whereas heading south is free. It's just a prettier drive.
As for a good place in Cville to get picnic fare, I'd suggest getting sandwiches from Durty Nelly's or Little John's. Little John's has better sandwiches, but they are often served hot, so maybe Durty Nelly's might be better to pack with you in the car in a cooler. They also have some good deli side salads too. You might also want to consider hitting a Bellair Market, which has great sandwiches and stuff like that, even though it's inside a gas station. (It's wildly popular in town - people sometimes call it the gourmet gas station.) And of course there's always places like Whole Foods or Integral Yoga or Foods of All Nations where you'd have a wider selection of a little more upscale take out food, sandwiches, side salads, etc.
I've always preferred driving south on the Blue Ridge Parkway, myself, but it's hard to go wrong with either route.
A favorite afternoon during my years in Charlottesville was to hit the Bellair Market for their great sandwiches and some chips, and then heading out Route 250 all the way to the Blue Ridge Parkway (it's a bit slower-paced than I-64, and always had a nice country drive feel to me). I'd then turn south on the BRP, and head to the parking lot for Humpback Rock (about 15 minutes south of I-64). The hike up to to the rocks is about 45 minutes (it's strenuous, in terms of elevation change, but the trail is well maintained and is something you can do in tennis shoes). You can then sit out on the rocks and enjoy a 270 degree panoramic view of the Shenandoah Valley as you enjoy your lunch.
Another vote for Bellair Market.
I think driving North on Skyline Drive offers more panoramic views, but the trees along BRP seem a little nicer to me. Either way is nice.
Thanks so much. Great input!
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