I've taken my friendliest ball python out into the grass and he seems to like it. As others have said, it's all about knowing your snake, his comfort level and being able to interpret his body language. Kahlua seemed very relaxed and enjoyed slithering around in the grass, and since it was right around dusk, the heat and humidity levels were similar to what he was used to. As long as he is not at risk of getting into the road or getting lost, it can't hurt to try it. It also makes for some fantastic photo ops