First off, here's the pic:

It's from black and white film negatives that belong to my grandfather. Hand-written on the paper they were wrapped in is "Sept 1958".
Of course, it has to be kept in mind that it could be that the film was developed in September of 1958, the pictures weren't necessarily taken then. BUT, I also had a roll that had "Aug 1958" written on it, so I didn't think it was too far behind in time.
In 1958, my grandparents lived in East Palestine, Ohio. And, on the "Aug 1958" roll, there were pictures from a family trip to New York City.
So, my guess would be that this is a picture from the trip home to Ohio from New York City. I can't tell from the landscape where exactly this picture was taken, although I have seen many scenes like this on my trips on the turnpike in PA between Philadelphia and Pittsburgh and on my trips driving north from Philadelphia to Binghamton NY.
The car on the road, is (I believe), a 1953 Chrysler Windsor 2-door. This conclusion is based on a conversation with a guy I work with who's hobby is working on cars. He showed me a picture that we matched to the back of this car so I'm pretty convinced. But I'm willing to consider other suggestions as always!!
When I look at the possible route using mapquest, I see that it's basically a straight line between the two places! I had no idea.
That road that is highlighted across PA is Interstate 80. The history of that road that I found on wikipedia notes that a small part of the road (near NJ/PA border) was completed in 1953, but other parts of it were not even started until 1959! So this easy highway crossing of PA would not have been possible in 1958.
If I go to google maps and do the same destinations but tell it to avoid highways, it doesn't look that different:
BUT, even though it looks similar, when looking at the route steps for this, there are a LOT of different roads used, so there's no one road that this picture is likely from.
So then! Conclusion then is:
It's likely the photograph was taken sometime between August-September 1958 while the family was in the car driving from NYC to East Palestine, Ohio.
As a point of reference as well, here are the photographs that were taken right before and after the one shown above:



