On the day we left 5/20/08 We took Bronx river parkway to the Taconic parkway to the end(I would recommend taking Rt.22north all the way to Hoosic,Ny. Thats what we took on the way back,and it was great),then we took some small roads (can't remember) to Troy,Ny. and took NY Rt.7 which turns into VT Rt.7 East ,got off the manchester exit and took Rt.11 East to Rt.103 to Ludlow(My Hometown).
Then on 5/23/08 we left Chester and took Rt.103North to Rutland and then got on Rt.7 all the way to Burlington IN THE POURING RAIN.wasn't that bad though,Kinda fun.(I would recommend getting off Rt.7 in Middlebury and takeing Rt.116north if you are in that area,much nicer road.)
Then on 5/24/08 we headed back south and took Rt.116south to Middlebury,VT then got on Rt.7south and took that all the way to Rutland,VT. and got on Rt.103 South to the Folks place in Springfield,VT.
Last we headed back to NYC 5/25/08
We took Rt.11 west from Chester,VT to Manchester,VT,got on Rt.7 south all the way to Hoosic,NY ,then picked up Rt.22 south ( The best part of the ride,also could have had something to do with the weather!) took that all the way to 684 back to NYC.
I recommend heading up to VT it is amazing.
Andy750 Keep us posted how your trip goes.
Any places/towns you plan on going specifically?