Not in crazy shape at the moment, and it's been a while doing a loaded tour... but I'm thinking about doing a one to two week excursion from New York City, October is the time I'll be able to do it... any suggestions for which direction to go? Route planning advice much appreciated.
Camping yes, but I'm thinking I am going to skip bringing cooking gear... some motel nights are completely fine by me as well.
Just want to get away from NYC for a couple of days to a week plus, and haven't been able to decide where to go.
Nothing too insanely hilly, I don't know if I have the legs for that at the moment
If a car can be added to the equation, you can throw your bike on your car rack and drive up to Cape Cod. The main rail trail from Dennis to Wellfleet is nice and flat, and once you get to Wellfleet there are the park and dune trails you can explore. Problem is that in October it's probably getting cold up there.
I don't know what your support possibilities are, but IF you could scrounge the transport on either end here's a great ride for somebody who's not in tri-athlete shape (and I'm not in that shape either) but wants an adventure: start in McKeesport PA (10 miles south of Pittsburgh) and ride the Great Allegheny Passage to Cumberland MD, then the C&O Canal path to DC.
It's a great ride, almost all wonderful trail in great condition. Generally flat with a climb in the middle - but the grade is kinder riding west-to-east. There's a lot of info on the internet on this ride. The tough nut will be getting to the start, and getting home from the finish.
People do this with pure camping, and others do this with just motels/BnB (that's my way). Total milage is about 350.