Is Pawling a good place for singles?

I agree with TracyD. The lack of nightlife or any real opportunities to meet new people makes me think that Pawling's not the best place if you're looking to expand your social circle.

In my opinion, most of Westchester/Putnam/Dutchess isn't great for singles unless you stick to White Plains or some of the arty/hipster areas like Beacon. There's so little nightlife and most of the towns seem more geared to families with kids. But I'm sure there are singles in Pawling and similar towns who don't find it hard to date- there's probably just more driving involved.