A century ago, islanders could travel from the harbor to Siasconset by train

When Nantucketers rode the rails, Annual 2017 Cape Cod Life | capecodlife.com

ART CONTEST WINNER • Acrylic painting by Nick Glaser • Grade 12, St. John Paul II High School

Unlike many of Nantucket’s quaint cobblestone streets, which have well-known histories, Easy Street’s origin is as murky as the fog that frequently envelops this waterfront roadway. What can be said about the picturesque one-way is that the town officials who chose the name, some time between 1918 and 1923, must have had a wry sense of humor.

Easy Street, which boasts a stunning view of Nantucket Harbor, was built on the path of the dearly departed Nantucket Railroad, a privately funded enterprise that operated—in fits and starts, but mostly fits—from 1881-1918. Although it ran in the red for most of its checkered history, the Nantucket Railroad had a rich history of derailments, de-coupled cars, engine failure, shifting tracks, crashes, and other calamities; miraculously, only two people were killed by the train during its 37-year run. In short, the Nantucket Railroad never led to “Easy Street” for anyone, especially the company’s owners and investors.

According to Mike Harrison, chief curator of the Nantucket Historical Association, 19th-century railroads were rarely profitable ventures. But even by the day’s standards, the Nantucket Railroad was the Rodney Dangerfield of railways. In other words, it got “no respect,” especially from the islanders. According to separate 1909 editorials in Nantucket’s Inquirer and Mirror newspaper, the railroad was “termed something of a cross between a farce and philanthropy,” and “for years has been the object of ridicule in both rhyme and story.”

While locals did use the train, which they called “the cars,” the narrow-gauge railroad was originally built to transport potential home buyers and investors from Nantucket Town to new seasonal developments that were sprouting up on the island’s south shore. Many of the property developers also doubled as railroad investors.

“Various entrepreneurs were creating seaside resort communities at Surfside, Tom Never’s, and ’Sconset, and they needed a way to get people from here to there,” says Lee Saperstein, a retired college professor who is leading a current effort on the island to convert the old railway path into a historic “rail trail” for walkers, runners, and bicyclists. “Some of those real estate developments did not succeed, but some did. ’Sconset, a fishing village, was relatively successful, becoming an artist’s colony right around the [end] of the [20th] century.”