We recently visited the Star in the Valley winery which is just off of 81 west of Fort Royal. A lovely little property with amazing views. I especially enjoyed the Field Star White, and my H liked the Cabernet Franc. They don't offer food, but you are welcome to bring your own snacks or meals.
https://www.starinthevalley.com/
Another place I remember is Revalation which is a bit west of Culpeper. We went in the Fall a few years ago and they had a bunch of outdoor seating...the trees in color were amazing. The wine was nice, tastings served in these tiny glasses which were so cute. Again, not much food but you're welcome to bring your own. Most seating is outside which is lovely when the weather is good.
https://revalationvineyards.com/
Earlier this summer, we were in Charlottesville and visited Carter's Mountain Orchards. Amazing views and really good ciders (which is what my H prefers). The cider donuts were awesome too. It's right by Monticello.
https://chilesfamilyorchards.com/carter-mountain-orchard/