Hi there,
I'm orginally from Queens and moved to Wappingers when I was a teenager b/c my family moved. Now I live in Fishkill which is the next town over (I'm 27 now).
The nearest train is New Hamburg which will give you a 1 1/2 hr commute directly into Grand Central Station. There are also some express trains (for rush hour) that will get you there in 1 hr and 15min. I do this commute everyday on the train b/c I work 2 blocks from Grand Central.
As for the drive.. your talking anywhere between 1hr and 2 hrs.. depends on traffic and which part of Manhattan you want to go to. I would say an average of 1hr and 1/2 dirve.
Nightlife...LOL. Not highly recommendable. Dont get me wrong, there are some clubs/ bars but they will not be what you are used to. Clubs/ bars are not very hip to say the least. Most clubs/ bars are in Poughkeepsie, Newburgh or NewPaltz (mostly just bars where I am in Fishkill). All these towns are 15-30 min away from Wappingers.
Area in general is very family friendly, no side walks (this drove me CRAZYwhen I moved from Queens), slow paced, quiet, lots of beautiful scenery, little diversity, and the people are very friendly. Homes are reasonable and you can get much more for your money there.
I would suggest you look at the villiage of Fishkill actually. I think your transition may be a little easier from there. You can walk (on sidewalks!) to shops/ resturants/ bars. You are close to the highway for easy commute to the city and about 10 min from Metro North. You're also about a 10 min drive from malls, gyms, all kinds of stores and resturants.
It took me a long time to adjust to this lifestyle when I first moved here. It was SOOOO extreemly quiet to me! That was so amazing. At night when it is dark, it is VERY dark. There are very little street lights and nobody outside at all. Everyone drives everywhere because everything is like 10-15 min away. When it snows, there are huge mounds of snow..nothing like Queens. What elese...let's see...Not very culturally diverse. I was used to having friends from all types of cultural backgrounds & here, there are mostly caucasions.
I hope this was helpful