East Hampton was something of a backwater until nearly the dawn of the 20th century as compared to Sag Harbor, which the Long Island Rail Road linked to the rest of the world starting in 1870. The train line to East Hampton took another 25 years to complete.
The Sag Harbor line is long gone, but one can find traces of where the tracks once were in the Long Pond Greenbelt, where I went for a walk not long ago with a friend. One trail there follows a long, straight run of embankment that once supported the train tracks. A telegraph line went in along the tracks and was completed in 1873. Bits of the glass insulators that shielded the wire from contact with the poles can still be seen here and there in the woods. Kidd Squid brewery off the main Sag Harbor parking lot occupies what was once the passenger terminal at the end of the line.
The Long Island Rail Road was no great shakes, at least according to a New York Herald correspondent who traveled to Sag Harbor in 1873, describing it as run by a man “as thoroughly despised on Long Island as Nero ever was in Rome” and the rail cars themselves, “a knock-kneed, groaning, swaying and thirsty caravan, mounted on wheels moving along at the will of an evil genius called a conductor who takes your tickets and besides does the duty of a brakeman. . . .” Nonetheless, Sag Harbor people were pleased to have it.
The Sag Harbor line extended from Bridgehampton and was used until the eve of World War II. But this was modern times compared to the rail line on the North Fork; the tracks reached Southold village in July 1844 and Greenport just a matter of weeks later. The Greenport line had success carrying passengers bound for Connecticut by way of the steamships they boarded there. Similarly in Sag Harbor, the steamship Shinnecock, among others, docked at Long Wharf, awaiting passengers to ferry across Long Island Sound.
For a time, Sag Harbor was the terminus of the main rail line east, however, after the completion of the track to Amagansett, Austin Corbin, the railroad’s primary owner, had the main-line trains run through East Hampton instead and served Sag Harbor by shuttle. This meant that passengers had to disembark at the uncovered Bridgehampton station to be loaded onto the smaller shuttle. In Wainscott, East Hampton, Amagansett, and so on, passengers enjoyed uninterrupted travel. But after the railroad was sold in 1897, new management restored the main line run to Sag Harbor. East Hampton erupted at the change. A “meeting of indignation” quickly followed at Clinton Hall. This changed again a short time later, as the slower shuttle was not able to “make time” to the satisfaction of the railroad brass.
As far as I can see, there was only one life lost in connection with the Sag Harbor trains. In the summer of 1908, a locomotive fell into the water while backing two coal hoppers down Long Wharf to fuel steamers bound for New England. The engineer, Joseph Smith, was killed, though the fireman was able to get clear. Crowds gathered near the wreck to gawk. Some 300 feet of new track had to be laid to get a crane close enough to remove the engine from the bay.
These days Long Wharf is covered with cars most of the time, and it is difficult to imagine how things used to be.