PP from Kingston here. I’m also loving that someone called Kingston “hipster!!” I’m glad my hometown is getting some love these days because I think it great there.

Also I also loveeee Santa Fe in tivoli and can confirm that the food is great! They also have locations in Kingston and Woodstock. Another fav restaurant my family loves is Aroi in rhinebeck. Really great Thai food.

My family still lives in the Red Hook area. I've taken the train, flown into Albany and Newburgh, and drove. The Thruway will be jammed around the holiday, no doubt. When I've driven for Thanksgiving, we usually leave very very late Tuesday, or very very early Wednesday, and come back Saturday. The station at Rhinecliff does have taxi/Uber but I'm not sure of rental car places in the immediate area.

Agree the weather will be cold and not pretty. But the river is always nice to look at. I'd recommend Poet's Walk in Red Hook. Vanderbilt also has some nice views, and if the road down to the river is open (right before the exit), it's one of my favorite places to hang out. I've never been to Mohonk, but some close friends recently did a hike and said it was amazing. Even in the cold, I imagine the views would be lovely.

If you're around Bard College, there's a garden near the Blithewood mansion that is amazing. I've only been in the spring/summer, so I have no idea how it looks in the Fall...but it's stunning. This past summer we drove up to the Albany Rural Cemetery...it was actually a very pleasant and calm place. I think they have tours and walks.

In terms of meals, I love the Terrapin Bistro in Rhinebeck. Mercato in Red Hook is quite good...earlier this year the chef was on some Bobby Flay show. I've had good experiences at Santa Fe in Tivoli. Bubby's Take Away Kitchen is good, not as good as the burrito stand they have in the summer, but it will do in cold weather. Cancun's, Charlie O's, and the Curry House are all okay.

And thank you to the PP who mentioned that Red Hook was quite hipster. You made my day.

I'm from Kingston and theres a lot of nice places to go in the area. Rhinebeck is great with some awesome restaurants, Kingston as well! I also second the recommendation for Mohonk, although its pricey to stay there! New Paltz is another fun area with some good places to eat. The traffic will probably be heavy on Wednesday going both ways on 87 though so be prepared if you want to drive. Amtrak goes right into Rhinecliff though (one town over from Rhinebeck and its a great option). Hope you enjoy the HV its great

Olana is lovely https://www.olana.org/

I hear that Hudson, Kingston, and Redhook are quite hipster these days.

The whole area is beautiful but the weather will likely be gray and cold.

Check out the colleges in the area. Bard has an art museum and a Gehry theatre on campus.

If you’re trying to eat Thanksgiving out, reserve early.

Try having Thanksgiving at one of the restaurants at the Culinary Arts Institute. And perhaps check out the West Point campus? There are historic houses up and down the valley. It's still lovely, even at that time of year although as someone else pointed out, most of the leaves will be down.

Mohonk is fabulous. I have stayed there a number of times although always in the summer.

Anonymous wrote:Troutbeck in Amenia is a lovely inn.

Amenia is far from most things.

Why don't you rent a house and let DC invite college friends from the west coast who aren't going home for the holiday to join you for Thanksgiving? We regularly spend the thanksgiving holiday in that area and I love it. We spend Wednesday and Thursday morning cooking, watch movies at night and go hiking on Friday. There are so many good hikes in the area. Storm king and beacon are also fun side trips. We also drive from DC. We always drive after 8pm, usually on Tuesday night, and it hasn't been bad (but our stop is n. New Jersey; we drive up to Hudson valley on Thursday usually).

Kykuit or maybe tour West Point.

Troutbeck in Amenia is a lovely inn.