Hudson, NY- heard many opinions
 

Some say it's funky and cute and quiet in a hip way....and within 2 hours of NYC. I'm intrigued. Heard different opinions. Any personal experiences?

I've been there for an afternoon from other locations in the Berkshires. Good antiquing. It's near Frederick Church's home, Olana. Have you read this?
http://en.wikipedia.org/wiki/Hudson,_New_York

It's a nice daytrip along the Hudson. Exactly what are you looking for in terms of making it a fun day?
As mclaurie noted, it's near Olana, which is definitely worth a visit.

Hudson is great. It is one of our favorite places to visit for a a daytrip on a sunday.
The main street is lined with old, beautiful buildings and is very, very charming. There are many great antique shops - selling antiques from all eras. And there are some delicious and trendy lunch spots (we like Baba Louie's pizza ) as well as some atmospheric coffee shops.
The scenery around Hudson is very beautiful - the classic upstate New York farm landscape. So the drive up is pretty and rural.

I wouldnt call Hudson "undiscovered" though - and the main street feels upscale in a "NewYork weekender" kind of way.
The side streets however, are a bit weird. The charming aspect fades out the further from the center you get. At one end of town there is actually a single high-rise "ghetto-type" building. Its very strange.

Hudson is an old fashioned New York industrial town that was first almost abandonned and then gentrified about 20/25 years ago. It now has a bunch of antique places and similar in the center - but of you jead to the outskirts a lot of the dilapidation still remains.