They wandered from town to town entertaining the whole way but the paying gigs came from royalty and special occasions such as weddings and holidays.

Previous answer is so close but misses a couple of essential points. Travelling entertainers (troubadours and trouveres) went from town to town looking for paying gigs. This COULD be from weddings, and royals, but most often would be in taverns (bars). The ‘royals’ in towns would more likely be barons, mayors, dukes, etc but this required the entertainers to be of certain renown. Just like today, you can’t walk in off the street as an unknown and expect to get on stage in front of the queen or something. In the old days just like today, you needed a name, or someone wealthy or famous to vouch for you.

The other way travelling acts could work was if they were in permanent employ of someone. Thus, they would be court entertainers, there to perform for the lord and lady of the house and guests. These people were more like servants than the travellers, but again, CLASS could change that. The most sought after entertainers could be rock stars in their own right.

From wikipedia:
Throughout the Middle Ages most histories were written by religious clerics who frowned upon the type of performers who juggled, called ‘gleemen’, accusing them of base morals or even practising witchcraft. Jugglers in this era would only perform in marketplaces, streets, fairs or drinking houses. They would perform short, humorous and bawdy acts and pass a hat or bag among the audience for tips. Some kings’ and noblemen’s bards, fools, or jesters would have been able to juggle or perform acrobatics, though their main skills would have been oral (poetry, music, comedy and storytelling).