Traveling by train from Washington DC to Bridgeport makes an awful lot of sense. Assuming that you are referring to the Acela Express when mentioning "the fast one", the Acela Express does not normally stop in Bridgeport, though it does not seem impossible for special arrangments to be made in this particular case. If such an arrangment was not/could not be made, then the Terrapins would have had to change trains no later than Stamford for a regional Amtrak train to Bridgeport, or take the Acela Express to New Haven and bus back to Bridgeport(very likely). One can also charter a train car in which the team can sit exclusively(also very likely). Still in all, I absolutely love the idea.