First visit to Hudson Valley
 

My husband and I are going to visit the Hudson Valley in May 2023. We have never been. We will be coming from Rye, NY in a car. We only have a Friday and Saturday. We enjoy good food, wine and the outdoors. We are looking for a place to stay and things to do. What town should we stay? Someone suggested Rhinebeck? Thoughts? Thanks

Try to have a meal at the CIA. Reservations are necessary for lunch and dinner, but breakfast can be had without reservations; it is excellent.

For things to do, browse through this photo album:

https://flic.kr/s/aHsjsqN921

I think some of those photos were Olana House where we had an interesting tour. Also liked the river cruise. Four friends so we rented an air b&b. Another uear we visited Saratoga Springs and had a great food tour which staryed at the farmers market but the tour might be out of business. Can't find their website. We must have gone in September before covid. The farmers markets around us are doing business so even if the food tour is out of business the farmers market is still probably large and vibrant. We tasted the water at a fountain nearby.

Outdoor sculptures (huge) in a nice park can take up a day at Storm King, if the weather is nice. Bring a picnic lunch.
The Rockefeller estate at Kikuit is very nice. Needs reservations. Choose the complete tour.
If there is a state fair or crafts fair (Rhinebeck or New Paltz) there is another goal.
Have fun!

I recommend staying in Rhinebeck. We visited about 10 years ago. Didn’t stay overnight, though. Forgot where we stayed. Rhinebeck is very pretty and has nice restaurants and small shops, not your typical chain stores.
We also visited Roosevelt’s house in Hyde Park.

I highly recommend Rhinebeck, also. It is so charming and well situated, we had a wonderful dinner there, but sadly, I can't remember where. If no accommodations are available there, we stayed in Hyde Park at Journey Inn Bed and breakfast. It was wonderful and the breakfast was fantastic.

We loved visiting Roosevelt's Home and Library, which is also his birth site and burial site. Kykuit, it is on a gorgeous property and the art collection is wonderful. There are many other former private mansions which are available to tour. Storm King is very impressive and has wonderful views, but you need cooperative weather. We loved touring West Point! You need a reservation. They operate every day of the week, but since your are going in May, that is not available on the last weekend which is graduation.

We missed out on CIA(Culinary Institute of America) by not getting reservations soon enough. I am only spelling it out because when I first saw it I thought what? The government agency? Next time!

Rhinebeck is very quaint and has good restaurants and unique shops, but it tends to be busy. Personally, I'd go farther north in Columbia County to Kinderhook. It's a bit beyond Hudson and features fantastic restaurants (The Aviary!!!), some with outdoor seating, and a terrific Bottle Shop that often has Friday night events. Bring or rent bikes and check out the bike path. You'll be in close proximity to Olana, Catskill and the Thomas Cole museum and a number of art galleries.