Even though I am not a foodie either, I would recommend what we did when we visited the Hudson Valley a few years ago--have dinner at the St. Andrews Cafe at the Culinary Institute of America. You will feel like you are dining in fine restaurant (which you are) but at casual restaurant prices. Also, while we wore slacks and nice sweaters, they are perfectly fine with casual dress, including jeans and sneakers.

Also, I would recommend a visit to and tour of the U.S. Military Academy at West Point. It's a fascinating place with some fabulous views over the river.

There's so much to see in the Hudson Valley. You could easily spend 4 or 5 days there ... or just a weekend.

Hyde Park and the CIA are both relatively close to Poughkeepsie, but if you drive up north toward Albany, there are quaint towns like Hudson (antiques stores, decent restaurants, a Shaker museum and a little sheep farm outside of town) or Chatham (more interesting stores, some decent restaurants). There are also historical sights like Martin Van Buren's birthplace (in Kinderhook, I believe). There's also Rhinebeck, a little more arty and expensive.

There's also Kykuit, which is beautiful. I know I'm all over the place geographically, but the Hudson Valley, while fairly compact, is pretty rich in stores, markets, and historic sights.

We stayed about 4 days in Rhinebeck and explored the HV from there. We loved it and want to go back and spend more time in HV. I think u will find all the things u mention in the HV. As mentioned Rhinebeck is an upscale little town (Chelsea Clinton had her wedding there.) and lots of New Yorkers have houses in the area and visit. We liked it and it was an easy place to use as a base to do day trips. In terms of time, from reading your TR in SEAsia, u like to move quickly so I would imagine 4-5 days might be plenty. U could c quite a lot in that time. Potentially u could choose 2 areas to stay -- lower HV and further North and maybe stay a few days longer doing it that way.

You've gotten some good advice. For dining, definitely include the CIA in your plans.
As for top attractions, I put the following at the top of the list:
*Kykuit, the Rockefeller estate in Pocantico Hills (adjacent to Tarrytown)
*The Storm King Art Center in Cornwall
*Olana, artist Frederick Church's home in Hudson (and, as Doug already mentioned, the village of Hudson is an interesting stop as well).
Here are two good websites to check out:
hudsonvalley.org
hvnet.com

We spent six days driving from Tarrytown to Kinderhook and back, and certainly could have spent more time in the area.
Some of the things we liked best:
Kykuit
Boscobel
Manitoga
Roosevelt sites
Vanderbilt Mansion
Olana
River cruise
Mohonk Preserve
Huguenot Street
Walkway over the Hudson
Storm King
Washington's HQ
West Point
Things we saw that wouldn't make my A list:
DIA: Beacon
Martin Van Buren site
Kingston Maritime Museum
Senate House
Fort Montgomery
Things we considered but couldn't fit in:
Locust Grove
Montgomery Place
Staatsburgh
Clermont
Cedar grove
Constitution Marsh
The CIS was closed while we were in Hyde Park, otherwise we would have taken the tour and eaten in one of their restaurants.

Storm King is our favorite place in the lower Hudson Valley.

Storm King and Olana are wonderful. Hudson is fun to poke around in, especially if you like art and/or antiques, though it does tend towards the precious, imo.

I live inthe area and I like Abrams lists, except that I think diaeacon is world class contemporary art, so would put that in the must list.

Rhinebeck seems to make sense as a central place to stay - lots of good restaurants at all price points, but if staying at Beekman Arms be sure NOT to stay in main building, and don't eat there.

Also, be sure to check which side of the river your various destinations are, as you can only cross at Poughkeepsie or Rhinecliff or way up just below Hudson.

You may want to take a look at my trip report; click on my name to find it.

Another big vote for Olana. We visited on our way back from PA to Vt in late November and really enjoyed it. The grounds and setting are spectacular and the house is fascinating. Thomas Cole's home is also right across the Rip Van Winkle bridge and we will go back to see that and the upstairs rooms at Olana (the second floor is closed during the winter tours).

Near Chatham mentioned in other posts you can see Shaker museums in NY and MA.

Don't bother with Thomas Cole's house. We were singularly unimpressed and greatly disappointed with the facility. Plus, the guide was pathetic!
The best time to go to Olana is during the foliage season. The view of the house and the trees is spectacular as you walk down towards the river.

If you like wine, google the area. There are many wineries, some of which produce good wines.

The Hudson Valley is both very beautiful (even winter if you get it under a coat of snow) and very historic. There are a number of quaint towns with cute shops (some junk and some very expensive antiques) as well as a ton of restaurants. You can see a little in 3 days/4 nights - or stay longer and see much more. A refuge of the uber wealthy from the days of the dutch padroons down through the Rockefellers and associates - don;t miss some of the incredible estates.

If you like a variety of things to do, such as wineries, history, architecture, art, food, shopping, outdoors, etc., then 4-6 days to do BOTH sides of the Hudson River should be just enough. If you plan on staying two nights at each lodging location, you should have plenty to explore without ever being bored or driving too much.

Enjoy!

The Hudson Valley, as everyone says, is a beautiful place. Hudson is a wonderful town as is Chatham - I am biased because I lived in both Chatham and nearby New Lebanon. When you are in that area you are also close to the Berkshires, so add Stockbridge to your list as well and perhaps Great Barrington and enjoy the "little" places in between.

Well, we didn't have time for everything, but we kept this thread handy, and managed to squeeze in tours of West Point, Olana and FDR's home and library, a visit to the grounds at the Vanderbilt mansion, a walk across the Hudson on the walkway, poking around Cold Spring, Hudson, Rhinebeck and Saratoga Springs, and a visit to Storm King Art Center (we are not museum people, but we absolutely loved Storm King). We had some good meals - excellent lunch at the Apple Pie Bakery at the CIA ( excellent wild rice soup and roasted mushrooms, delicious flank steak and cavatelli carbonara, fantastic rice pudding and chocolate cake "pop"). I got a macaron to go and didn't eat it until the next day - it was still great - it was goat cheese and apricot). We also had good meals on the casual side of Terrapin in Rhinebeck and at Sushi Thai in Clifton Park (where we stopped for the night after getting pounded by an incredible rainstorm near Albany...I couldn't wait to get off the road). All in all, it was a wonderful respite. The views throughout the valley are astonishingly beautiful.

Hi sf! Glad u enjoyed your time in Hudson Valley. Loved Terrapin. Had my first Dark & Stormy drink there. We plan to get to Storm King this trip in July. So...how was the rest of your trip, wedding, graduation etc? How did your outfit work out?

This is amazing trip, I will take some tips from it. I enjoyed reading it. Thanks