We'll be driving from Northern VT down to Pleasantville, NY on Nov 12th(Fri). We've got the whole day and would like to stop along the way and do something fun. Any ideas?

Have you visited the Shelburn Museum near Burlington, VT? Looks like the drive from Northern VT is about 5 hrs, going the fast way (ie down I-91) Going that way you could also stop at the museums in the quadrangle in Springfield, MA or the Atheneum or Mark Twain Home in Hartford, CT.

If you drive down rt 7 instead, slower but prettier IMO, you could also stop along the way.

Outlets in Manchester Vermont?

There are two Pleasantville, NY's... one near NYC and the other across the state towards Erie PA... which one?

We'll be going down one side of Lake Champlain or the other. We are headed toward NYC (did not know there was another Pleasantville...)

Shopping's not our thing, but perhaps a flea market, an interesting museum, or something to do with animals, nature...
The Shelburne Museum is great, but it takes a day or two to see it all, and I think it's closed this time of year.

there is a brewery in pleasantville, captain lawrence. and you can check out the grounds at blue hill at stone barns nearby.

Saratoga Springs is a very nice little city. Beautiful park with mineral springs, lots of good restaurants and shops, lots of history.

You might want to take a look on at my trip report "Ten Days on the East Coast" which should have been titled NYC and the Hudson Valley. Click on my name to find it.

Cooperstown

Dia Beacon
Storm KIng

I'm going next week, and I plan to drive the Taconic Parkway, stopping in Rhinebeck and at the Walkway Over the Hudson in Poughkeepsie.

The Culinary Institute of America in Hyde Park, if you want a fancy lunch made by the students, and I'm going to the Eleanor Roosevelt National Monument, which is the house she lived in whenever they were visiting Hyde Park. Lots of history there!

Hope you have a fun drive! No snow yet, right?

The new walkway in Poughkeepsie is supposed to be great.
http://www.walkway.org/

Less fancy but also at the CIA and extremely well prepared:

http://www.ciachef.edu/restaurants/apbc/menu.asp

Unfortunately, Storm King is closed for the season, and I wouldn't recommend a walk on the Poughkeepsie walkway this time of the year. Too cold.
DIA Beacon is a good recommendation. Then, there's the FDR home and museum in Hyde Park.