"Driving is work" depends very much on what you're driving and where. Driving can give you a freedom to see the country rather than just pass thru it. It offers an opportunity to get off of the beaten track and change plans spontaneously that simply don't exist otherwise. My family once made a spontaneous detour to the Grand Canyon just after it snowed that was magical - it would never have happened had we not been driving.
As the ancients said: "Life moves pretty fast. If you don't stop and look around once in a while, you could miss it."
Well - that's why said when and where.
The OP talked about going "upstate" - I'm guessing east coast US, which like much of Europe *really* wasn't designed with modern automobiles in mind. I can see it being a severe chore in those places.
But - I live in the US southwest, where everything is designed with the automobile in mind. Good weather 90% of the time, mostly modern wide highways, and trains are a very limited, inconvenient option. We go driving for pleasure - you just need to avoid a few well-known ugly high traffic areas - like the airports and big train stations in city centers. And when you arrive - you don't need to rent a car like you would if flying, you already have your own.
I keep thinking about people who *like to cook* - it looks like a lot of work to me. But they seem to enjoy it, and doing it yourself does mean a lot more choice...
@Biggles @futurebird that says more about the USA than driving vs trains. Flexible train tickets can also allow last minute detours, as long as service exists. Also, even though it's flexible, driving is still work.