One of the Clapps’ famous contemporaries in Pittsfield was Oliver Wendell Holmes, poet, dean of the Harvard Medical School and the great-grandson of Jacob Wendell. (Mr. Holmes is known for being the father of Oliver Wendell Holmes, Jr., who became a U.S. Supreme Court Justice.)
Another neighbor on nearby Holmes Road was Herman Melville, one of America’s most celebrated authors. According to the Berkshire County Historical Society: “Herman Melville spent many summers in Pittsfield visiting his uncle’s farm (on South Street). In 1850, he decided to move to Pittsfield permanently, buying a home that he named for the artifacts he dug up while plowing. It was at Arrowhead that Melville wrote Moby Dick along with three more novels. 16 short stories and one volume of poetry. Many of his stories and poems were set in the Berkshires, including several set at Arrowhead. ‘A great neighborhood for authors, you see, is Pittsfield,’ Melville wrote in 1851.'”
John and Sara Morewood purchased Melville’s uncle’s farm on South Street in 1850. Later the property became the Pittsfield Country Club. Mrs. Morewood was well known for her humanitarian work during the Civil War. Sara’s son, William, married Herman Melville’s niece, Maria, and they lived at Arrowhead.