Yeah. Love to hate on MA, but they’re alright when you actually get down to it.

Brattleboro is extremely not on the way between Boston and Burlington, though.

Hanover parking’s been much more manageable lately, FWIW. If someone’s reference point is Boston or Burlington, it’s a breeze. Don’t disagree with the rest, though.

If you want to stop halfway-ish, you’re looking at the upper valley. Besides the Hanover options mentioned by sibling, Three Tomatoes pizza in Lebanon and Tuckerbox (Turkish place) in WRJ are good toddler-friendly places that don’t take you as far off of I-89.

Montpelier has some decent options too, but by the time you’re there you might as well just drive through to Burlington.

Edit: oh, or New Thailand in Leb, just off exit 18. Good food, super convenient from the highway.

Worthy is great, but be aware that it takes you 15-20 minutes out of your way each direction.

Tuk Tuk is solid, but for dumplings, Base Camp is the place to go in Hanover.

Yeah, I shouldered ours (70lbs) out about 3 miles on Passaconaway. At least that’s mostly flat-ish, but still a pain.

Across the river, but you’re in the upper valley, so Base Camp Cafe in Hanover!

Don't forget to cup the balls.

Also they’re all gonna get eaten by bears by the time you move here.

Yeah, upper valley has three relatively painless ways to NJ: the train from WRJ, plus either Dartmouth Coach from Hanover to NYC or Cape Air from LEB to NYC, followed by NJ transit. Or driving. We have used all over these pretty regularly in the past.

These will all be fine (and mostly have water available en route, either from huts or surface water). We hike them with our dog. Only caution I would offer is to ask if the dog is used to that mileage? Ours will sometimes get her paws rubbed raw if we go much over 10 miles / day, and fireman carrying her out sucks.

Get a copy of the AMC white mountains guidebook, which has detailed info on all of these hikes (and good cautions for hikes with a lot of exposure that it sounds like you want to avoid).

If your goal is to make the trip to NJ easy, you don’t want to be on 93, you want to be close to 91. Being over by 93 just adds an hour+ to your drive for no benefit.