We'll be leaving EWR about noon on a Sunday and driving NW about 150 miles (app 2.5 hours drive) to Hancock NY.
We'd like to turn this into a scenic 7 hour hour drive.
Moderately off direct route is fine.
I spent a little while looking up towns that might be of interest and came up with:
Sleepy Hollow / Tarrytown
Cold Spring
Beacon
Warwick

Are some of these good choices?
Any other suggestions?
In addition to the towns is the drive at all scenic?

Oh boy, here’s another example of when you give more info recommendations can change. I know from your other thread you are planning to rent your car at EWR rather than un NYC to save money but do you realize that Sleepy Hollow, Tarrytown, Cold Spring and Beacon are all on the NYC side of the Hudson River. They are much easier to reach directly from NYC rather than going from NYC to EWR then back across the Hudson River to visit those towns which are directly north of the city. So more food for thought.

regardless of which route you take to Hancock the first hour or so of your trek WILL NOT be anywhere near scenic. It is basically all light industrial areas or bedroom communities. You won’t get scenery until you get to northwestern NJ or past Whestchester County (north) of NYC.

Sorry, didn't have time to give you a suggested route when I made previous post.

If you are not to concerned about drive times, don't mind straying from a direct route and want scenery consider the following (keeping in mind the first 45 to 60 minutes won't be scenic):

From EWR (or NYC, if you decide to bite the bullet and rent your car in NYC) drive north toward George Washington Bridge (Fort Lee, NJ) and get on northbound Palisade Interstate Parkway (here's where the scenery begins) drive north through Harriman State Park (aka 7 Lakes Parkway), travel westward and link up with Route 17 West near Woodbury, NY. Continue on Route 17 (aka The Quickway) and exit in Chester, NY. Take country roads to Sugarloaf (a small craft village where you can stop for lunch and browse the shops, Continue on to Hancock. You can plot out this route using Google Maps or Mapquest.

Roams,
The plan may change.
Originally we figured to leave NY around 9:00-9:30 and go directly to Hancock.
Now we're thinking of either leaving NY about 4:00 or so and driving there then or leaving 10:30 - 11:00 and making a day of the ride.
I'm not giving more info. Things will probably change but we're not quite sure what we'll end up doing.

I'll look at your suggested route and see if there are any other stops of interest along the way.
Thanks.

Oh, and picking up the car wasn't strictly a money thing as you are making it appear. The main reason is to avoid driving in the city.
In fact, when I first mapped out the route with the towns I suggested, I had us driving on the west side of the River until Sleepy Hollow.

And now what happened.
= = = = = =
We walked out of our hotel at about 11:00AM
We took a side entrance so as to not conflict with the taxis in front.
Within a couple of minutes the Uber driver was at the end of the block. He saw us and drove up to us.
We acknowledged each other and I helped put our suitcases in the trunk.
We got in the car and things went downhill quickly.
I thought being able to speak English might have helped. But he couldn't really do that.
When I told him Newark Airport he looked at me as if I was asking about a foreign destination. Maybe it is.
Well, we got to Newark Airport but not with him.
= = = = =
We started to drive up the west side of the Hudson River. At some point we decided to get off the expressway for a snack. We pulled into a mall. About a half hour later we walked into a supermarket to pick up a few things.
When we got to the door we realized it had clouded over and we had to wait about an hour for a torrential downpour to pass.
It cleared rather quickly and we drove to and across the Tappan Zee Bridge to Tarytown and Sleepy Hollow. We wandered around for a while and I took some pictures at Philipsburg Manor even though it was closed by then.
When we got back in the car we realized time had gotten away from us so we decided to skip any more stops and headed towards Hancock.
It rained on and off all the way so the drive was slower than we expected. It was still light when we got there.

The next day was beautiful.

Thanks for the help.