Maggie's Farm

I spent 20 years working for Big Blue just down the road. My recommendations are:

If you like old planes - this is a fun show: https://oldrhinebeck.org/

https://en.wikipedia.org/wiki/Walkway_over_the_Hudson - old railroad bridge, now a pedestrian walkway. Great views, not for the acrophobic.

http://www.canalmuseum.org/depuy-canal-house - this was, for a few years, a wonderful restaurant. It's being returned to its historical roots. There are many remnants of old canals to explore in the area. More on that can be found at http://www.canalmuseum.org/ .

I hesitate to mention this because you are likely familiar, but in Hyde Park, the CIA isn't a spy shop, but one of the world's great cooking schools. They run several restaurants staffed by the students. Great dining and engaging conversation with your server and the maitre d'hotel - https://www.ciarestaurantgroup.com/new-york-restaurants/

Not too far away are a number of estates and mansions along the Hudson. https://www.nps.gov/vama/index.htm https://www.nps.gov/hofr/index.htm are a couple I have enjoyed.

9D from the Bear Mountain Bridge up through Beacon is nice. River Road in Rhinebeck, just south of the Kingston Bridge is pretty. Chelsea Clinton was married at an estate someplace along here.

The town of Woodstock (not where the music festival was held) is an interesting place for crafts shopping. They used to have a nice local playhouse there as well.

That's enough, I'm starting to feel a little homesick now.