My husband and I are planning a trip to New York for 5 nights followed by a road trip about 10-15 days, possibly through New York State. Any suggestions?

Last September we did a long weekend in Saratoga Springs with a day trip to Hildene in VT. I was surprised at how much I liked the area. We did a food tour that began in the wonderful farmers market. I skipped the trip to the racetrack but my friends had fun. On another vacation, my husband and I enjoyed the Adirondacks but the main attraction for us was the furniture and museum. We aren't hikers.

Consider Storm King (outdoor sculpture park).
And Kykuit Rockefeller estate.
Whe4n your dates are set, or when you are setting them, check out dates and locations of craft fairs, art fairs, county fairs, music festivals, etc.
Are you into wine? There are wineries of interest in the Hudson Valley.

I would do a search for trip reports in the Hudson River Valley. There are many interesting sites to see in addition to those mentioned in the last post, including the Olana and Thomas Cole homes (Hudson River artists) and the National Historic sites with the homes of Franklin Roosevelt and Eleanor Roosevelt in Hyde Park.

You might also enjoy the Finger Lakes region which has wineries and other historic sites and/or the Adirondack park area.

What are you interested in?

I found your SE trip report = 3300 miles in a month. Great trip!
I have some ideas and will return to this thread. But to start with, the Hyde Park area, the CIA and then off to more.
Trip Report - Touring South East USA

Back to see how long my "loop" would be. 14 hours of driving and 858 miles. Not sure that's of interest. But anyway...
A friend and I did a weekend trip to the Hyde Park area and the Roosevelt homes recently. Loved it and ate at the CIA every day. Great trip (out of New Jersey).

Another friend (a Fodorite) and I have taken several trips in PA, and I absolutely love Frank Lloyd Wright's Fallingwater in the mountains of PA. We've stopped at the Flight 93 memorial twice (over several years) and hope to return. Driving out that way would take you through the Amish countryside of PA, which is simply lovely. I used Bird-in-Hand as a point on the map. You could end up in Philly or DC and sightsee there and/or drive back up to Newark (or take the train). The mileage return includes a loop in and out of Newark, NJ.

Those include some of my favorite places and beautiful drives in the countryside. Based on your SE trip report, I think you may enjoy some of those.

Also, what time of year are you planning this trip?

Do you want to return home from a NYC area airport? Otherwise you could take a train out of New York Penn Station to a destination in western or northern New York State and rent a car there. If you ever wanted to go to Niagara Falls, you could get off in Rochester, Buffalo or even Niagara Falls NY. With a rented car you could also visit the Rock & Roll Hall of Fame in Cleveland.

This thread contains a list of things to see and do in the Hudson Valley. We were there 4 or 5 days and barely scratched the surface.

Hudson Valley

Probably have to be Autumn now, September/October.

Obviously cheaper to do that but open to suggestions.

September/October should be a good time to visit and for a road trip. Hotel prices in NYC will be high. You will also run into trouble finding accommodation in areas people visit for the fall foliage, especially on weekends, so it might be good to make some tentative reservations that can be canceled soon.

My husband and I visited Fallingwater on November 1st, the day after a major wind storm. Apparently the foliage there had been very beautiful the week before.

As for the Beacon prices, it was a little tricky to get to the flexible rate during the recent insider Winter Sale offer.. The link from the Beacon took me to Advanced Purchase options that could not be cancelled. I had to go in and change the sale code that had come up. The flexible rate is of course higher but we didn't want to commit to specific dates so far in advance. (the codes in this case were BIS and BISA)