[lifetimeliguy]

I am a LI guy (note the name) and drive to Vermont frequently. My favorite way - take the Hutch Pkwy to 684 to NY 22. NY 22 is a beautiful road that rides the extreme eastern border of NY. You will go through some nice towns, great scenery all the way. It does get a bit lonely when crossing the Mass Pike (I-90) area but you will be fine. You can literally look over to CT and Mass to the east, the border is that close, and the mountains are beautiful.
Make a right on NY 7 in Hoosick (NY), follow that into Vermont, it becomes VT 9. You can stay on VT9 to Wilmington ,then take VT 100 north as recommended earlier.

-or stay on NY22 at Hoosick and cut over NY149 to Granville (NY), follow to VT30 north. VT30 is a great road with views of the Adirondacks to the west . In October the peaks of the dacks may already have snow. It's unforgettable scenery if you get a perfect clear day.

Most of the ride is decently flat, except on NY22 around the Mass Pike area and VT9.