Both of these footpaths behind the houses on Orange Street are remembered but no longer passable.
In 1928 Grace Barnes of Nantucket petitioned the Land Court to register land at the end of Gardner’s Court and asserted “ownership in the right of way known as Cat Alley.” On June 28 of that year, the Board of Selectmen received a document from the Land Court that “determined for the benefit of the members of the board just where Cat Alley is located.” Merle Turner in her 1929 article about Nantucket’s smaller and more obscure byways describes Cat Alley as a narrow passage extending north from Stone Alley, connecting with Gardner’s Court.
In a 1954 letter to the Inquirer and Mirror, Henry A. Willard of Washington, D.C., referred to Cat Alley as Stone Alley’s “ambiguous off-shoot.” In 1974 Cat Alley came up again in a description of property, and it appears on recent utility maps
A decade ago Cat Alley was still open, but now it is overgrown and impassable. This may be agreeable to neighbors, because it had become an unfortunate locus of late night drinking, littering, and general annoyance.
An unofficial footpath ran in the opposite direction from Stone Alley to Flora Street. In 1914 a correspondent to the Inquirer and Mirror wrote that the steep bluff face behind houses on Union Street “was called by the children of past years ‘the jumping hill’ because it was a sandy cliff, just right to slide and jump down.” The same children called the footpath along the top of the bank the Indian Trail. In 1963 an adult—botanist Frank C. MacKeever—learned about the trail. He wrote, “I asked Mr. Swain if it were permissible to walk through this strip of land. He informed me that all the youngsters of the neighborhood travel over it by a path which they call the Indian Trail—a name by which the strip has been known for years.” MacKeever scrambled up to the path and was rewarded. He wrote, “I was overwhelmed with the beauty of the wilderness of this narrow strip of land right in the heart of town. You could look into the backyards of buildings that abut Union Street and Orange Street and see in many of them beautifully landscaped gardens. Nevertheless, on either side of the trail I saw plants I have not met with elsewhere on the Island.” He urged preservation of the Indian Trail and its rare native plants “not for just 50 years, but for many more years to come.” MacKeever was drawing close to retirement and planned to move permanently to Nantucket, where he might have been a force for preserving the Indian Trail, but on the eve of retirement he died, and the trail lost its champion.
In 1972 it was reported, that some property owners had recently closed off sections of the trail. Up until then, “it was a favorite play spot for Nantucket youngsters.” By 2005, according to the Gardening by the Sea column of the Inquirer and Mirror, the Indian Trail was completely overgrown with English Ivy and other invasive plants. Five years after that, a new homeowner on Orange Street proposed to install a swimming pool to the edge of the bank where the Indian Trail once ran, eliciting protests from below on Union Street.
The spirit of Frank MacKeever would be distressed at what became of the fragile strip of wild land he hoped would be preserved for posterity.