I drive this route roughly once a month about 8 month a year.

The direct route is congested and unpleasant. There are two shunpike possibilities: the western route through Pennsylvania (you could go to Gettysburg, the Dutch country, Valley Forge, or New Hope on route, but not all of them).

The second is the "far eastern" route through Annapolis and the Eastern Shore of Maryland to Lewes, Delaware, where you can take a ferry to Cape May, NJ, a town noted for its extravagant Victorian architecture. You can then drive north on the Garden State Parkway (no trucks) to the Tappan Zee Bridge across the Hudson.

Once you cross the Hudson (either route) you have a variety of possiblilities. Probably the easiest is to take I-684 to Brewster, then 84 to Hartford, then on to Boston. You might also take the Taconic Parkway (again no trucks) to route 23 in Martindale, NY. Turn east to drive through the Berkshires (Great Barrington) before joining I-90 (the Massachusetts Turnpike) for the remainder of the trip to Boston. Very scenic. Very slow on a Sunday in summer.

Thanks everybody. Just as I am about to forsake the drive in favor of flying, you tempt me with descriptions of a pleasant drive and timely trains. This is really tough. All options have their pros and cons.

How many hours of driving are these alternate routes? I am guessing 12 hours or more, assuming you don't get lost? Split into 2 days, that still doesn't leave a lot of time for stopping at sights. I guess it just depends on how much time you want to spend in the car.

OP has already abandoned this idea and posted elsewhere re: choosing between plane and train.

But - as I said at the other post - I'm sorry he/she has given up the idea of driving - it's not like the car windows are covered over and you can't see anything along the way. You can sightsee in motion, and have the option to pull over and LOOK any time you want, if you aren't on an interstate. Two days that allow at least 8 hrs. on one day and 4-6 on another for extra-car activity aren't bad - have done it, have enjoyed it, would do it again, on that very route.

Haven't given up the idea of driving yet. Thanks for the suggestions and thoughts.

I would not drive as I95 is not the best road. Not only are there delays but there are huge potholes.

There are no decent rest stops.

I used to love flying from Regan Airport. The subway is so convenient. Fromt the subway one can take a quick trip to Arlington Cemet if there is delay. I am not up to date on the Airport...............Have a good trip !!

When are you going? Starting August 16th, Southwest will have five non-stop flights daily between BOS/BWI.