I also live in CT and have driven to the southeast many times, and I'll give a tip: it doesn't matter where in MA you are, you cannot transit the NYC-DC corridor without running into rush hour at some point unless you avoid the area entirely (which I often do). Driving from the I-91, I-84, or I-95 entry from Massachusetts into Connecticut all the way to anywhere on WDW property is approximately 21-23 hours behind the wheel, and you'll need at least four 15 minute stops for fuel (just a gas and go by the time you've decelerated, fueled, and re-accelerated onto the highway adds 12 minutes). It's 24 hours of driving.
If OP wants their car there with their stuff, which isn't unreasonable, they should drive to Lorton, VA. Leave at 3:30-ish AM, get into Lorton, they load your car and drive the rest of the way for you, so the next morning you arrive, actually refreshed.
https://www.amtrak.com/auto-train