Forget for a moment the question of why you'd want to do that, on a slow trip that would involve changing trains several times. The New London Day reports Connecticut legislators are considering a plan that would extend that state's commuter-rail system, which now ends at New London, to either TF Green Airport in Rhode Island or Worcester's Union Station - both of which are now also served by MBTA commuter rail.
The move, by legislators from the eastern end of the state, comes at the request of Electric Boat and Pfizer, which say they'd love to have a way to get their workers who now live past New London to work.
If it happens, and the Day says the tracks are already in place, that would let a Bostonian travel to TF Green, transfer to CT Rail, get to New Haven and get on an MTA Metro North train to Grand Central Station, hie over to Penn Station to get aboard a New Jersey Transit train to Trenton, where you'd take a SEPTA ride down to Philadelphia.
And then, from there, you'd take a train to Newark DE, and hope that by the time you get there, Maryland's MARC will have completed a possible extension there, which would let you get to not just Baltimore but Washington, DC, for a connection to Virginia's VRE and a trip south to Spotsylvania, where you'd then turn around and do it all in reverse.
So why would you do it? To say you did, of course.
In 1903, a couple wrote about their honeymoon taking trolleys from Wilmington, DE to Maine. Five years later, a New Yorker wrote a similar book about his trolley trek from New York to Maine. And while the latter is a fairly grumpy account - he seems to hate most of the things he encounters - he starts:
If the reader of this short tale has never ridden by trolley from Manhattan to Maine he should take half a dozen days off some time during the Summer months and do so. It will prove a revelation and a revel to him from start to finish.