Winter view of Longfellow House's front gate, 1904

Born in 1844, "Charley" Longfellow was the beloved first child of Henry and Fanny Longfellow. In 1863, he ran off to enlist as a private in the Union Army during the Civil War, and eventually received a commission as a lieutenant in a cavalry regiment. Miraculously, he survived a bout with malaria and what could have been a mortal wound in his back, which he received while on campaign in Virginia. After his wounding, he turned to sail. His 1866 voyage to England on his uncle's yacht the "Alice" set a record for a transatlantic crossing. From there he traveled on to Paris, and then to Russia and back. He accompanied brother Ernest to Europe on his honeymoon in 1868-1869 but soon lost interest in completing the Grand Tour and accepted an invitation to go to India where he stayed for 15 months, traveling around northern India and the Himalayas. He returned home via the newly opened Suez Canal. His Indian experiences are documented in some of the many photo albums he assembled. In 1871 Charley set off for Asia. He lived in Tokyo for almost two years. The furniture, works of art, porcelain, textiles, and books he sent back to 105 Brattle Street were early contributions to what became a "Japan Craze" in the United States. From Japan, Charley went to China and also managed to visit the Philippines, Singapore, and Thailand before returning home in 1874. Between 1875 and 1891 he went to Cuba, Mexico, Scotland, Ireland, the Canary Islands, Madeira, Italy, North Africa, Turkey, France, the West Indies, Egypt, Scandinavia, Spain, Portugal, Wales, Colombia, Australia, and returned several times to England and Japan. Unlike other gentlemen travelers of his era, Charley wanted to experience life in his travel destinations, rather than merely observe it.

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