Are there any pick-your-own farms in Pawling?

I haven't come across one in Pawling proper, but in nearby Poughquag (Beekman), there is one called Barton Orchards. That shouldn't be too bad of a drive from here, maybe about 15 minutes or so.

If I'm not mistaken, you can pick a lot more than just apples here -- their website lists the types of produce which are available at any given time. And yes, this includes pumpkins for the fall/Halloween.