Tomorrow we are going to take it the rest of the way to Conway NH and the start heading south west thru NH to Mass to Penn.. to head west Home to Detroit
If your hitting Conway NH, you most likely will be going thru the Kancamagus highway to get there. If not, use it to get out. Worth the trip.
If you have the time, a trip to Mt Washington would be cool.
Obviously, you want to avoid eastern and most of central Mass. A ride down the west side of I-93 on back roads down to Keene NH is nice. Then grab rte 32 south down to the Quabbin Reservoir area, but you might want to stay on the west side of the Quabbin down rte 202 south.
If you stay on the east side of the Quabbin, take 32A instead of 32, much nicer.
Rte 9 west from there is not bad except going thru Amherst and Northampton MA, but once thru them, the Berkshires, in Western MA (and CT) are excellent.
Rte 2 west is highway like until you get west of Greenfield , MA. then it's nice.
If you can hit rte 112 or 116 in western mass, you'll like them. Also, either rte's 7 or 8 are good. If you hop over to NY, rte 22 is great.
Lots of options.
The thing about NE is, some of the secondary roads are in need of repair and a lot of that is up to individual towns. Some are better than others at that work.
Looks like you got a excellent weather weekend, enjoy it.