Northern Neck of Va to Sturbridge, Mass

One potential option may be to take Amtrak (from, say, Fredericksburg, VA to Springfield, MA, which requires changing trains in New Haven, CT). It would take 8-10 hours, it appears, with a few different reasonable connections throughout the day.

Here's what we do:

We usually take the loop around the west side of Baltimore when towing: in a car, the tunnel is fine - just a small toll.

Get off I95 north of Baltimore (like jog over to US 1 at Bel Air, MD), the objective being to get to US 209 up to I84. We then cross the river at Newburgh and chart a course for wherever we're going in New England. If you don't have an EasyPass, make sure you have cash on you for tolls at places such as the I95 bridge across the Susquehanna River leaving Maryland.

Rob

I-95 to the GSP to I287 over the Tappan Zee.

1. Take I-684 to I-84 to the Mass Pike/US20 or
2. If you're in a car stay on I-287 to the Merritt Pkwy to I-91

Avoid the section of I-95 from the Cross Bronx to New Haven if at all possible.