Septenary is right off the highway, making it easy to get to from Charlottesville. We also recommend Stinson and Veritas in that same area. There are many others to explore too.
Three Notch'd is a great option close to downtown and has a great food menu. Random Row & Starr Hill also have locations in town. Pro Re Nata is a cool space and often has live music, though it's a 20-min drive out of town.
Carter Mountain has a beautiful view of Charlottesville and has all your fall favorites: apple picking, cider, warm doughnuts, pies, etc.
This is a great spot for drinks and a view.
Explore Thomas Jefferson's beautiful home & grounds. They offer tours and there are walking trails and a good view of Charlottesville. Please visit their website for reservations.
Another historical home to visit. Beautiful walking trails in the fall. Please visit their website for reservations.