Agree with Ancient Mariner. Heading up I-87 is the easiest way to go from Staten Island to Montreal.
That said, here's an idea: Take I-91 North TO Montreal, and then take I-87 South FROM Montreal back home. Compromise!
I'll second the recommendation to stop in Northampton, MA. Also Ted's or White Hut.
If you're taking I-87, you could always stop in Glens Falls for a hot dog or 3:
http://www.roadfood.com/R...836-3736/new-way-lunch Also, just north of Glens Falls, off Exit 25 (not Exit 24 as previously written) of I-87, in Chestertown, is a great little place for Italian or Steaks - "The Place":
http://www.theplaceitalia...out%20The%20Place.html The Italian food there is superb. Great basic red-sauce favorites (Manicotti, Lasagna, Chicken/Veal/Eggplant Parmagiana, etc.). The sauce is superb.
<message edited by TwoJays on Wed, 11/3/10 2:50 PM>