Pyle had been submitting illustrated poems and fairy tales to New York publications since 1876, and had met with success. The Merry Adventures of Robin Hood was the first novel he attempted. He took his material from old ballads and wove them into a cohesive story, altering them for coherence and the tastes of his child audience. Pyle's book continued the 19th-century trend of portraying Robin Hood as a heroic outlaw who robs the rich to feed the poor; this portrayal contrasts with the Robin Hood of the ballads, where the protagonist is an out-and-out crook, whose crimes are motivated by personal gain rather than politics or a desire to help others. The novel was first published by Scribner's in 1883, and met with immediate success.
Pyle's work ushered in a new era of Robin Hood stories. It helped solidify the image of a heroic Robin Hood, which had begun in earlier works such as Walter Scott's 1819 novel Ivanhoe. In Pyle's wake, Robin Hood has become a staunch philanthropist protecting innocents against increasingly aggressive villains. Along with the publication of the Child Ballads by Francis James Child, which included most of the surviving Robin Hood ballads, Pyle's novel helped increase the popularity of the Robin Hood legend in the United States. The Merry Adventures also had an effect on subsequent children's literature. It helped move the Robin Hood legend out of the realm of penny dreadfuls and into the realm of respected children's books. After Pyle, Robin Hood became an increasingly popular subject for children's books: Louis Rhead's Bold Robin Hood and His Outlaw Band (1912) and Paul Creswick's Robin Hood (1917), illustrated by Pyle's pupil N. C. Wyeth, were children's novels after Pyle's fashion.