Cold Spring, NY, may be just the place you want. The Hudson Line of MetroNorth stops right in town. The town itself is right on the Hudson River, beautifully situated where the rive is most fiord-like, surrounded by mountains. There are a few restaurants, quaint houses, and plenty of antique shops for browsing.

Hardly any of New England is within 1 to 1.5 hours of NYC. The only places would be the closest ares of CT - which are mostly very upscale suburbs. You can certainly visit Greenwich - which is very cute - but much more trendy than Olde New England - and the shopping is mostly designer or very upscale home crafty type stuff.

What you're talking about are old Hudson River industrial towns that have been reborn for a trendy market. Cold Spring is cute - but not really THAT New Englandy.

If you want something with real history go to Tarrytown - which is not New England but originally colonial Dutch - and has some interesting houses to tour as well as a cute downtown.

A lot of what many people consider that "cute New England type town" is in fact art galleries and antique shops.

While I do like Cold Spring for dinner now and again I think you could see just about all of the town in about an hour.

As others have said your limit of 1 to 1.5 hours is really quite limiting.

The NY town of Rhinebeck is one stop before Hudson on Amtrak and might fit your bill. It's just over 1.5hrs by train, then you have to get up the hill into town (taxi - as I don't think there's a bus). It's big enough that there is more than one shop, yet small enough that it's retained some of that old quaintness. Not New England, but close enough.

I believe tickets on Amtrak are about $25 per person, each way, which makes for a pricey 1 day getaway.

Tarrytown is also a good, much closer to NYC option, as nyt suggested. There are also several historic mansions/estates very close by, the most prominent is Kykuit, the Rockefeller Estate. MetroNorth RR usually has a special train/admission package. Philipsburg Manor is a historic, working estate that dates back to the early Dutch settlers. It's a working farm, not a fancy modern era palace.

http://www.hudsonvalley.org/content/view/12/42/

If you're looking for that picture postcard Norman Rockwell / Currier & Ives New England town you need to venture to somewhere like western Mass, which requires a car a more time.

You might check out Madison, CT.

You might want to check out City Island in the Bronx. You can get there by subway and bus.
http://www.forgotten-ny.com/YOU'D%20NEVER%20BELIEVE/cityisland/cityisland.html

Let us start of with the basics. What constitutes a New England town, let alone a cute New England town? What town in New England would you consider prototypical?

A town with a stream where a mill used to be?

A leafy town center?

A white-steepled church by a lake or town center?

Snow in July?

What about one of the Hamptons towns?

http://travel.nytimes.com/travel/guides/north-america/united-states/new-york/long-island/the-hamptons/overview.html

Excellent questions from Mr. Adu. Therefore I would suggest Stony Brook LI, NY and Northport,LI, NY. Also Litchfield, CT. New Milford, CT. More as I think of them.

All of you locals are ignoring City Island. It is a cute New England town.

Thanks for everyone's suggestions. I guess I shouldn't have used the term New Englandy as I am really just looking for a cute/quaint town to visit to get away from the city. Right now our top two choices are Tarrytown or Cold Spring. Daughter liked the idea of Kykuit and possibly Phiipsburg Manor, with a stop at Blue Hill Cafe for lunch (unfortunately the full restaurant is only open for lunch on Sunday which won't work for us.)
If I can find out if we could see a cadet parade at West Point, then Cold Spring might win out but right now the parade schedule was only for Fall 2010 - not sure what if anything is happening in May.

Lefteris Greek Restaurant in Tarrytown is one of my fave casual real deal greek places! We bring home a bottle of dressing on each visit. The best pita and dressing and high quality feta. . . yum!

Have you changed your mind about renting a car? Just wondering since to combine Cold Spring and West Point you would definitely need to drive yourself.

I always enjoy an afternoon visit to Katonah, NY....about an hour train ride north of NYC.. Train service a couple of blocks from town. Town is coomprised of a main street with numerous small quaint shops. It's a fun casual walking afternoon visit.

see the movie "City Island"--its a cool place,especially off season--in season you need to speak spanish.
I also like Rye NY or Scarsdale