Howard Pyle was born in Wilmington, Delaware, on March 5, 1853. His parents were William Pyle, owner of a leather business, and Margaret Churchman Pyle, a painter. In 1881, Pyle married Anne Poole, a singer, with whom he had seven children.

As a child, he was instilled with a love of reading and books from his mother. Pyle dreamed of becoming a storyteller and tales like Robinson Crusoe, Grimm's Fairy Tales, and Arabian Nights tempted his young imagination. He daydreamed through his days at the Friend's School in Wilmington, followed by schooling at a small private institution. Pyle's parents felt that their son should attend college upon graduation, but the aspiring artist had no plans to enroll at a university. He was devoted to developing his dream of becoming a painter. His parents lacked the adequate funds to send him to study art in Europe. Instead, Pyle traveled to Philadelphia to study with F. A. Van der Wielen. Financial problems forced Pyle to seek artistic guidance in America, ending a long-standing tradition that artists must travel abroad to study art. He remained in Philadelphia for nearly three years and later returned home to the family leather business. His minimal formal training consisted of three years study in Pennsylvania, coupled with courses at the Art Students League in New York, New York. 

In 1876, Pyle traveled with his father to the Chincoteague Islands. He compiled an illustrated narrative of the trip, which was accepted by Scribner's Monthly. Upon receiving word that his story would be published, Pyle traveled to New York City. He abandoned a career in leather for a life in literature. A year later, Pyle's first piece, "A Wreck in the Offring," was published in Harper's Weekly. With the publication of Pyle's first work, the young author realized the importance of illustration in the cultural fabric of the art world. Eventually he returned to Wilmington, while still continuing his relationship with New York publishers. In 1883, one of Pyle's most famous works, The Merry Adventures of Robin Hood of Great Renown, in Nottinghamshire, was published as a series of stories that would entertain generations of children and adults. Amidst the excitement of a producing a classic children's book and raising a family, Pyle also taught illustration in 1894. He began educating students at the Drexel Institute of Arts and Sciences in Philadelphia, where he won the loyalty of his select students. His idealistic approach to illustration and high standards for excellence attracted aspiring artists. He conducted special classes for extraordinarily talented students in Wilmington at the Howard Pyle School of Art. Pyle passed on his gift of expertise to students for no charge, even building a set of studios for his apprentices to practice their art in Delaware. He also held summer classes in Chadds Ford, Pennsylvania. The rural locale served as a fashionable spot for city dwellers to escape the excitement of city life. Pyle set up a studio in an abandoned mill. His makeshift classroom became the Brandywine School of Art, responsible for the education of a family of great artists: the Wyeths. Andrew, N.C., and Jamie Wyeth carried out Pyle's illustration traditions in their volumes of immensely popular work.

While Howard Pyle is credited as greatly influencing the realm of children's literature, he never received any formal awards for his work. However, his legacy of literary contributions continues to live on in the hearts and minds of children and adults who enjoy his works today. As Harold von Schmidt said in his article for The Illustrator in America, 1900-1960, Howard Pyle was "probably the greatest illustrator America has ever produced."

Howard Pyle died on November 9, 1911, in Florence, Italy, failing to recover from renal colic.