Can't go wrong in ME, NH, or VT! Depending on how far north you go, Colebrook, NH has the motorcyclists' monument... 9
https://www.roadsideamerica.com/tip/856 )and that would allow you some road time along the VT/NH border with Quebec as well. If you choose that route, stop in Derby Line, VT where the library is half in US and half in Canada and then enjoy the route through Newport.
http://www.rk-mass2.org/articles/north_border.pdf
Agree with 302... there is also a short route through Groton State forest in VT that is a great twistie route that connects 302 and Route 2... and Route 2 is another scenic road. North of that spot where 2 & 232 cross is Cabot and the Cabot Creamery -- stop for a tour and a cheese tasting. From there look for Route 15 and follow that west to 104.
On 302, you can stop at Rock of Ages Quarry in Barre for a tour, and definitely take a ride through the cemetery in Barre (no, really) to see the artisan work with their marble on the headstones.
Of course Ben and Jerry's (and ice cream tour and tasting is in Waterbury on Route 100/Route 2. South of Waterbury (off 100) is Route 17 which is the Appalachian Gap or Mad River Glenn. This is one of the mountain passes up over the Green Mountains. Last time I went over the "Ap Gap" it was in pretty rough shape, but that was probably about 3 years ago.
No matter which route you take across Vermont, pick up Route 2 north of Burlington and follow it up the Champlain Islands. Great route hopping islands before you cross into NY at the Canadian border.
If you do not want to go that far north, work your way over to Charlotte and take the ferry over to Essex, NY.
100 is one of my favorites, but that runs North and South.
http://www.rk-mass2.org/articles/Route100.pdf
Gee, all these different routes means you have to do the trip more than once to figure out which is your favorite!
Good luck and have fun. The planning is a good part of the enjoyment too!
Ride safe.
Bob
