How did Bear make a living going from one town to the next?
In the story, Bear is a wandering performer. In order to earn a living, he juggles leather balls, sings, and plays on his recorder as he travels from town to town. Bear originally learned these skills from the mummers group he joined after he ran away from the Benedictine abbey where he was enrolled. Instead of becoming a priest, Bear traveled all over England with the group of mummers and learned 'the language of song, of hand, of foot and...of laughter.'
When Crispin becomes Bear's apprentice, Bear teaches his young ward how to play on the recorder, to juggle, and to sing. Bear also demonstrates his dancing skills to Crispin. As Crispin watches in amazement at Bear's nimble moves, the older man announces that Crispin will be the one playing the recorder while he (Bear) dances, juggles, or sings for the crowd.
As Crispin has been declared a wolfs-head (who any man may hunt down and kill), the two have to make their way from town to town without being seen. Their final destination is Great Wexly, and they have to be careful not to draw attention to themselves. To earn a living as they travel, Crispin plays whatever song Bear instructs him to as the older man juggles, sings, or dances for the crowds that throng them. On occasion, Bear and Crispin earn money as well as bread for their troubles.