Have fun Joe, I wish you a safe trip. Port Jervis is an hour southeast of and Kingston is an hour northeast of me. I have many miles on Rt 44 from Poughkeepsie to the Conn line in the '70's as my first wife was from the northwest corner of CT
You will drive that old Plymouth thru some beautiful scenery. I hope you have the batteries charged in your camera.
If I read your post correctly, you are driving 209 from Port Jervis to Kingston, If you call me at 845-985-0206 when you get to Wurtsboro, I can meet you in Napanoch at the diner there in town if you are interested. Napanoch is apporx 20 miles east of here.
Above all, safe travels my friend,
Bob