Crispin says that he is traveling through a new world. In what ways is it a new world to him?
As Crispin travels with Bear, everything appears to be new to him because he's never been beyond the borders of Stromford. Up until his mother's death, all his activities have been confined to the village, where everyone survives at a subsistence level.
As Crispin travels towards Great Wexly, he finds that his position in society has changed because of his relationship with Bear. At the beginning of the story, Crispin mentions living in 'shadow' because he has no father. In a 'world in which one lived by the light of a father’s name and rank,' Crispin knew that being fatherless was a handicap. However, with Bear taking on the role of master and father-figure to the orphan, Crispin soon discovers that his horizons have been opened. As a performer, Bear is able to pass on the skills of his trade to Crispin. With these new skills, Crispin gains confidence and is soon able to see the world in a different light.
In fact, he becomes bold enough to explore the city of Great Wexly by himself and gets a great surprise when he glimpses Lady Furnival and her entourage. Crispin, in having lived a sheltered and walled-off existence, has never seen such wealth displayed before his eyes. What is even more amazing to him is the fact that the poor and the rich mingle in the crowd without trouble or upheaval. He would never have experienced this back at his old village in Stromford.
Another way the world is new to Crispin is that his life is now in danger after the sadistic John Aycliffe, the steward of Stromford, declares him a wolf's head. A wolf's head is basically a fugitive anyone can kill without fear of punishment. Even though Crispin has always lived in poverty, he has never before experienced the dangerous life of a fugitive. With Bear at his side, he soon discovers that greater forces are working to push back against the power hierarchy of England itself. These new experiences exemplify Crispin's new world of danger and trial.