Yes! It's so much fun, although my experiences weren't at a commercial farm or orchard. My favourite place to go fruit-picking is Tasmania, where my family and I lived for a few years. As the weather is no nice and mild (just perfect for growing apples) there are lots of wild apple trees growing on the sides of the small country roads where people have thrown apple cores out, and the seeds have germinated. When we lived there we'd sometimes go for country drives on the weekend and pick boxes of wild apples. Sometimes we'd also ask farmers if we could pick apples from their old neglected orchards that weren't being harvested any more. One day we were especially lucky and discovered a deserted orchard with the biggest and most fragrant Fuji apples I've ever seen! Needless to see, we used to have a lot of apple pies when we were down there, and I'd also freeze the excess, dry it and make it into jams. Sometimes we'd also pick wild blackberries too, but it's alweays important to be careful with those as often councils spray those to kill them off. If you're ever in Tasmania on holiday be sure to watch out for these...
There's definitely something special about picking your own fruit and vegies. These days most of us are so out of touch with the earth and nature, and growing your own or going food farraging is a great way to connect again.