Break Neck Alley was the name of the way that still exists down from the south side of Academy Hill Apartments (formerly the Academy Hill School) to Lily Street. There were steps at the very top, and steps remain despite some modernization.
Nantucket High School was established in 1838. In 1856 a large wooden building for the high school was built on Academy Hill. The school stood out as a landmark on the north side of town and was a source of pride to several generations of its students. One of them was Alliston Greene, who was born in 1866. In the 1940s Greene serialized his reminiscences in the Inquirer and Mirror, where he recalled that in his school days, the Lily Pond had a much larger expanse of water than in later years. On freezing winter days, the Nantucket High School boys would rush down to the pond to skate. The route they took, what Greene described as “the lane at the south of the yard,” was Break Neck Alley.
The wooden high school was replaced in 1929 with the current three-story brick building that housed grades 1-12. By then, the name Breakneck Alley had been changed. On August 7, 1909, the Here and There column of the Inquirer and Mirror reported, “The narrow, rocky passage-way leading from the school-house grounds on Academy Hill to Lily street, commonly known as Break Neck Alley, has been given the pleasing name of Sunset Pass, and has an attractive sign-board at its Lily street entrance. If the pedestrian who uses the alley does not keep both his head and heels under control, he is liable to see stars as well as a sunset.”
A month later the newspaper reported that “the passageway leading from the Academy Hill school grounds to Lily Street is no more,” having been rebuilt and made safe for pedestrians. Henceforth it was to be known by the new name of Sunset Pass. There were problems with run-off from the school grounds washing out Sunset Pass, however, so in 1913 the town invested in further improvements: “Sunset Pass (formerly Break Neck Alley) has been concreted and the conditions there greatly improved. It is thought the concreting of the ‘Pass’ above and below the cement steps will prevent further annoyance by providing a channel through which the surface water may flow.” The following year an appropriation was sought at Town Meeting to install a streetlight on the corner of Sunset Pass and Lily Street.
Once automobiles were permitted on the island in 1918, Sunset Pass was frequently mentioned in the newspaper because of concern for school children running into the path of drivers on Lily Street. Other mentions of Sunset Pass occurred with some frequency in property descriptions. Apparently the name was accepted from the first, and there was no effort to restore or retain the earlier name. Instead, with time, most people have forgotten that the way had any name at all.