5 day road trip from NYC (Montreal or elsewhere)

Hello everyone! My boyfriend and I (both in our mid-20s) are planning a fairly spontaneous post-Thanksgiving road trip. We have 5 days and need to start and end in NYC. I know this doesn't leave a lot of time, so we were thinking of going somewhere relatively close, such as Montreal, maybe a bit further than that but not by much. Does anybody have any advice on where to go (is Montreal a good choice? Any other ideas?), and if we do go to Montreal, where we may go on the way for a couple of one-night stops (Vermont, upstate NY, etc)?

Any and all advice would be much appreciated! :)

Welcome aboard the RoadTrip America Forums!

To be honest, one of the things I was happily surprised about when I lived in New England (Maine) was that relatively few New Yorkers seemed to realized how close New England was. That helped keep the number of tourists to a minimum. Montréal is only about seven to eight hours from New York and so can be easily driven in a day, even taking into account the border crossing. Montréal is a very cosmopolitan and bilingual city, so you can easily get by with little to no French language skills. Finally, there are two great, and nearly equal, ways to go between the two cities so that you can easily construct a loop trip.

What I'd suggest is that you consider such a trip, taking a day and a half to get to Montréal via the Hudson River valley, spending a couple of nights there and then returning via the Green Mountains of Vermont and the Connecticut River valley. What you would see during each of the three portions depends on your interests, but there is no shortage of scenic, historic, quirky, or just interesting sites for each and all of them. I'd be more than happy to give you a few specific recommendations, but would need you to narrow down your preferences first. As for overnight stops on the two drives, I'd probably be looking at (very roughly) Elizabethtown NY on the northbound Hudson River leg and Montpelier VT on the southbound Green Mountain/Connecticut River leg.

AZBuck