In 1891, the Ice Glen was donated by David Dudley Field to the Laurel Hill Association, the first incorporated village improvement society in the United States. As the association's existing property at Laurel Hill, which directly abuts the village center of Stockbridge, is separated from the forested hills in which the Ice Glen is located by the Housatonic River, the association built a bridge to connect the two properties. A trail still runs from Laurel Hill, behind the former Plains School over the bridge, through the glen, and exits on Ice Glen Road behind Villa Virginia.
Beginning in the late nineteenth century, annual torch light hikes of the Glen became popular.
In Moby-Dick, in the chapter "A Bower in the Arsacides," the narrator invokes the Icy Glen as the apotheosis of verdant nature run wild: "It was a wondrous sight. The wood was green as mosses of the Icy Glen; the trees stood high and haughty, feeling their living sap; the industrious earth beneath was as a weaver's loom … " Herman Melville was living not too far from Pittsfield when he wrote the novel, and he is known to have visited the Ice Glen on at least one occasion.
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