New England advise?

Which one first?

dayville is straight up 84 to CT rt 2 east to 395 north

chesterfield can also go 84 east to 91 north of going there first, if it’s rush hour, you can also take 87n in ny and run it up to 90e to 91n

either way 395, 190 and MA rt 2 will help you get to the other after the drop

there is a new pride truck stop open in Hartford too which is the same as the one on Chicopee (Springfield)

 

Your kidding? Four wheelers are a PIA!
At least you can have guns and not treated like a criminal .

OP one more option i would consider. If Dayville first, as said 190 to 2W then140N to 12N to Keene to 9W. Not sure this is alot faster but it is considerably shorter. You will go through couple little towns, pay attention to speed. Don't feed the bears.
If I am making trip, how I do it.

 

NEVER depend on your GPS unit.......NEVER!

 

Be prepared to wait a long time in Chesterfield. I’ve delivered there a few times, and it is slow! But, you have a Shell gas station on your right, right before you cross the bridge back into Vermont that has truck parking, and a Citgo in Brattleboro, just as you cross that same bridge, and just off the rotary, that has truck parking out back. Not many people use these, and you’re almost guaranteed to get a spot.
If the place in Dayville is the former Rite-Aid (now Walgreens, I assume) they’re pretty quick. If it’s the grocery warehouse right next to it, be prepared to wait and BE ON TIME FOR YOUR APPOINTMENT! I had to repower a load there once and didn’t make the appointment, and they make you reschedule or wait until everybody else is done, and then there’s no guarantee that you will be unloaded.
I’ve done these both several times. Easy, other than the waiting.

 

I wouldn’t mind runs up that way if it was smooth like the majority of i80 in pa. Last time I went that way I remember a hill, it was short, but it went straight down and I thought my truck would fall apart from how rough it was..

 

Yep I'm pretty sure you're talking about the very first hill on 84 after you get off 81. There's more craters on that stretch of road than there is on the moon...

 

There's a big section of roadwork in that area these days.

 

It's cleared up now, they got all the paving done finally. Unless they started back up again now that the weather broke

 

I88 in ny was the same way. Slowly but surely they're patching that up