Are there any good bike trails in the village of Pawling?

There's at least one that I know of in the area -- the Harlem Valley Rail Trail. An erstwhile rail line was converted into a paved bicycle highway up the eastern side of the county and will go well north into Columbia County when it's complete. The issue here is that it does not extend all the way down to Pawling. It's southern end is in Wassaic, which is two towns to the north in Amenia. This would probably be your best bet as far as biking goes, but unfortunately I'm not aware of any great biking trails in Pawling.