In the summer of 1838, Hawthorne had visited North Adams, Massachusetts and climbed Mount Greylock several times. His experiences here, especially a walk he took at midnight where he saw a burning lime kiln, inspired his story, originally titled "The Unpardonable Sin". Hawthorne had not written tales since 1844 when he wrote "Ethan Brand" in the winter of 1848–1849.
Melville is said to have taken part of his inspiration for Moby-Dick from the view of the mountain from his house Arrowhead in Pittsfield, since its snow-covered profile reminded him of a great white Sperm Whale's back breaking the ocean's surface. Melville dedicated his next novel, Pierre, to "Greylock's Most Excellent Majesty", calling the mountain "my own... sovereign lord and king". Thoreau summited and spent a night in July 1844. His account of this event in A Week on the Concord and Merrimack Rivers described his approach up what is today the Bellows Pipe Trail. Scholars contend that this Greylock experience transformed him, affirming his ability to do these excursions on his own, following his brother John's death; and served as a prelude to his experiment of rugged individualism at Walden Pond the following year in 1845.