Henry's parents were Yankees. Henry's father, Melanethan, was a descendant of Captain Josiah Starr who was born in 1657 in Massachusetts. His mother, Lucretia Nevins, was born in Connecticut. Melanethan was born in New York and went to the Albany Academy. He started his career as a clerk in a wholesale dry goods business--a kind of grocery store--in New York in 1839 and married Lucretia Nevins, Henry's mother, soon after.

Henry was born in 1840, shortly before the family moved to Florida, where his father worked as a cotton merchant. Henry's sisters Florida and Elizabeth were born during this time. In 1843 the family returned to New York because Melanethan did not agree with slavery and the treatment of slaves in the cotton fields of Florida. He worked as a banker in New York until he moved the family to Rockford, where he opened his own dry goods business.

In 1852 Henry has a baby brother, named Chandler after his grandfather. His sister Florry [Florida] is 10 and his sister Lizzy [Elizabeth] is 7. The following story takes place during the children's summer vacation from school. The story is based on events that Henry recorded in a diary he kept from 1852 to 1853.