Can I go rock climbing in or near Pawling?

In Pawling, I doubt it. There probably aren't very many rocks to climb in the first place, but there aren't any indoor facilities of which I'm aware, either. I have discovered, however, that there is an indoor rock climbing gym in Danbury, CT. I'd estimate that at about a half an hour drive.

For outdoor climbing, the only places I really know are out in Ulster County past New Paltz, but that's a long enough way from Pawling I assure you.