I lived in Poughkeepsie for three years. Outside of town is very pretty, and you can tryly enjoy nature and the change of seasons. In the town of Poughkeepsie the schools are excellent. In contrast the city is really a dump, with criminal elements and very few things to enjoy. (Bardavon theater is nice)

Poughkeespie has a typical suburban feel to it, with not a lot of originality, and lots of chain restaurants and stores.

The winters are cold with a lot of snow and not much to do.

I would say it’s worth visiting but not staying, since it can get pretty boring after a while.