When do you arrive? From the hints of your plans on the main discussion thread I suspect we will not really be in the same area at the same time, but possibly...
Monday afternoon 6 October. Planning to head out of town on the Tuesday and make my way northwards via a not-necessarily-direct route (I've never been to New England - or anywhere east of Ithaca and north of Harriman in upstate New York - so lots of potential options).
The public transport into NY city is very good. Sky rain from JFK to one of the nearby stations, depending on which line you want and then the subway system.
It sounds like we will not quite be close enough for shared O map adventuring, as I will be in Philly until Wed night before heading a bit farther north (New Paltz, north of NYC). I'm sure you will find some great terrain and pretty fall colors!