Hudson Valley/Berkshires Help
 

Need some advice. Planning a getaway to the Hudson Valley/Berkshires and ending up in Martha's Vineyard to visit a friend. We don't know the area at all though fairly frequent travelers to NYC. We live in New Orleans so we like good history and good food. Planning on early October flying to NYC for one night and then taking the train to either White Plains or Poughkeepsie to pick up a car. Leaning toward White Plains so we don't have to backtrack to Beacon. So question is where to stay in the Hudson Valley for one night? Cool town with a great place to stay and some great restaurant. Then we're headed over to the Berkshires. Lenox? Stockbridge? Then down to Newport/Martha's Vineyard. Question is whether it's worth it to pass through Newport or stay one night? Two nights in Martha's Vineyard is non-negotiable. Yes, it's a lot of driving around. If we gave up one night in Newport, we could stay 2 nights in Hudson Valley or Berkshires. Which?

There it is. Love to hear the thoughts of the Fodor Forum folks. Towns, hotels, restaurants, sights? All comments are welcome! Thanks!!

For food there is always the CIA. Their breakfast is great and not expensive. Reservations are probably necessary for lunch and dinner.

https://flic.kr/p/8KzW8J
Starting from the south, there's the Rockefeller estate (reservations necessary)

https://flic.kr/p/8KwNR4
On the western side of the Hudson there's the Storm King Art Center:

https://flic.kr/p/2hKNwUR
In Beacon there's the DIA

https://flic.kr/p/2gSxAGr
The Vanderbilt and FDR homes are close to each other

https://flic.kr/p/8KwR2c
https://flic.kr/p/8KwT8g
and farther north there is Olana:

https://flic.kr/p/8KA1iA
Rhinebeck might be a good place to stay but it is north of most of the sights mentioned. We had a nice meal in Le Petit Bistro.

https://www.google.com/search?tbs=lf...fi=hd:;si:;mv:[[42.03740579500035,-73.6577064748705],[41.84920147510295,-74.17269060572987],null,[41.94337307675909,-73.91519854030018],12]

Thanks very much for your ideas. Great photos. I'll check out Rhinebeck.

Check out both Rhinebeck, Hyde Park and Hudson.
And do not miss the FDR Home and Library in Hyde Park, a beautiful property, Eleanor Roosevelt’s childhood home is there too. It should be #1 on your list of what to visit.