Born in 1844, "Charley" Longfellow was the beloved first child of Henry and Fanny Longfellow. As a young child he was keenly interested in the comings and goings on Brattle Street and his mother observed "[he] promises to be a man of action." From the age of 18 he spent most of his life traveling in distant places. He and his brother Ernest attended Miss Jennison's school at the corner of Garden and Mason Streets and both enjoyed drawing. His journals from his early travels include drawings he made to record his impressions.
Always a risk taker, Charley lost his left thumb after a gun accident at the age of 11. Seven years later 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.