We have done that trip a couple times in the last few years. Even pulled our 5th wheel over the GWB once. Won't do it again. We live just below you (Exit 20).
Take the Mass Pike to 84 and then set your gps to the Tappen Zee.
Also, that's a long drive for a single day drive pulling a trailer. You run into potential traffic at a couple places which can really slow you down.
Remember to find a route around DC and Baltamore.