A lot of what you are considering as routes and overnights. If you are planning for the trip on a weekend you will gain some help as the roads will be more open. If you are going to hit DC beltway on a workday between 3-6 you will have a couple of hours added to your trip. To get to Rt 84 to Hartford you will be about 1.5 to 2.0 hours from NJ Turnpike to
84 by Newburgh and then about 90 miles to Hartford?
An alternate way is 301 to 10 to 95 by Jacksonville then on 95 to Rocky Mount, NC Overnight. Next day Rocky Mount to Wilmington Delware on 95. Next day from Wilmington, Delware to New Jersey Turnpike and Exit NJ Pike on to Garden State Parkway to NY Turnpike to Newburgh/Beacon bridge to Fishkill,NY. Overnight here (many places to stay) then next day on to Rt 84 and Hartford about 90 Miles.
Just another way to go? Good luck and enjoy your self
to NY Turnpike to near
Newburgh Bridge over Hudson River and overnight, (Many places to stay). Next
day Rt 84 to Hartford.