In 1855 21-year-old Walter Kittredge — singer, instrumentalist, songwriter and elocutionist — left his family’s farm in the Reeds Ferry section of Merrimack, New Hampshire, embarking on an adventure that would define his life. After this initial solo concert tour of New England towns, he began his long professional association with the Hutchinson Family Singers, originally of Milford, New Hampshire.

In 1860 Walter married Ann “Annie” E. Fairfield of New Boston, New Hampshire, when they were both 26 years old. After the Civil War broke out in April 1861 Walter, an avowed abolitionist, attempted to enlist in the Union army. He was rejected as he had recently suffered a bout of rheumatic fever. In the fall of 1863, while on his way home after visiting his friends the Hutchinsons at their family compound in Lynn, Massachusetts, Walter met an acquaintance who informed him that he had been drafted. No longer starry-eyed about the war as he had been in 1861, Walter dreaded the thought of leaving his wife and baby daughter Clara to join the conflict.