Known chiefly for his book illustrations, Caldecott was a gifted artist respected by his contemporaries. The Caldecott Medal which is given out each year for the most distinguished children's picture book is named for him.
In 1877, Edmund Evans, who was a leading colour printer asked Caldecott for illustrations for two Christmas books. The results were The House that Jack Built and The Diverting History of John Gilpin, published in 1878.
It was Caldecott's health among other things which prompted his many winter trips to the Mediterranean and other warm climates. It was on such a tour in 1886 that he was taken ill again and died in St. Augustine, Florida, just before his 40th birthday.