It started over a cup of coffee. My friend Nate and I were having coffee at ThreeBirds. I was back from HighEdWeb North Carolina and getting ready for WPCampus. He was basking in a delightful trip that he’d taken to DC recently and was interested in replicating the experience–a trip taken for the trip’s sake. We didn’t set ourselves many parameters, save that we’d like to knock it out over a weekend and we wanted to travel by train wherever possible. We settled on circling Long Island Sound.
Long Island stretches 118 miles, from New York City to the Atlantic Ocean. North of it lies Connecticut. There are two ferries that cross it, one between Bridgeport and Port Jefferson, about halfway across; the other between Orient Point and New London, at the eastern end of the island. The Long Island Rail Road comes within a mile of one ferry and eight miles of the other. The various rail services on the Northeast Corridor have direct service to the ferry terminals in Connecticut. We devised a plan involving eight trains, three ferries, and two buses. Looks simple on the map, right?