Is Red Hook the big local town, or will I be traveling to other areas to find things to do?

You're going to most likely be traveling to other towns. Most areas in Dutchess County have Poughkeepsie as the biggest nearby town/city, but Red Hook is a little different in that Kingston is the nearest population center of consequence. There are malls, a lot more restaurants, things to do and things to see. Kingston is sometimes a pretty sleepy town, but there are more things to do and places to go than in Red Hook. Poughkeepsie/Wappinger has more, but it's further away.