If you are gong to hit Interstate Highways all the way, the choices given will get you there. The tolls you will incur will be when you cross out of NY on I-84 into Mass. Taking I-84 you will not have to use the Mass. Toll Rd, although it is not that bad and the price is reasonable for the short distance you will go. Using I-84 You may want to take I-91, but it doesn't go to Boston, It will take you due North until you pick up NH-10 into Keene.
Are you in a hurry? If not, you may want to consider some alternative US Road routes. We just recently completed 4000+ miles and avoided the Interstates as much as possible. We were on some pretty nice roads. Yes, there are some stop and go towns, but to me that is just a break from the monotony of driving. My family lives in Central Mass and we have taken that trip "up North," a few times. One of my favorite drives is through the Delaware Water Gap (US-209) to I-84.
We definitely avoid I-95 from South of Richmond to North of NYC. I'm used to Houston driving so I'm not afraid of traffic, but that stretch of road will tire you out, and you do need a co-pilot navigator unless you have made the trip a few times in that direction. Some of the traffic delays can really get on your nerves, just not knowing why it is stopped and how long you will have to sit there.
If you need to go through any big major areas like that, try to plan on doing it on a Sunday, if you can - much less traffic and no rush hour traffic.
When we returned a few weeks ago, we came through Houston on a Sunday. We flew through except in one area that I knew we would have a short 5 minute slowdown. If I had wanted to I could have taken Hwy 146 out of Lufkin and avoided traffic altogether. Texas has some good roads, as do many of the other states. The US-Routes are federal funded and seem to be in better shape than some of the other secondary side roads, but all-in-all, we had some very good luck with roads on our last trip.
Enjoy, sight-see, take your time and see all the scenery.
Wayne MSGT USMC (Ret) & Earlene (CinCHouse)
2008 Winnebago Destination 39W
It is what it is, and then it is what you make of it.