The key in adding ensemble to any show is to not overwhelm the audience with additional bodies just for the sake of adding bodies. Given that, I think there are LOTS of opportunities in Into the Woods, Jr. to add MEANINGFUL ensemble roles: If your staging allows it, perhaps add a few customers/townspeople to the Baker's scene at the top of the show. Similarly, Cinderella's step mother could have OTHER household help, so it's not JUST Cinderella. If those other household helpers are treated BETTER than Cinderella, then it changes the dynamic between the step mother and sisters and Cinderella, showing that, even though they have the means to hire additional staff, they CHOOSE to mistreat Cinderella. For Jack & his mother, how do they make money? If they indeed sell Milky White's milk for income, perhaps have townspeople or customers stop by, only to be turned away by Jack's mother, indicating "no milk today". This shows how important the cow is to their livelyhood, and makes Jack's decision to do something desperate even more critical. The princes surely have their respective entourages. Give each of them a name and a job, and then dismiss them when appropriate. Have additional ensemble members serve as stage crew, but dress them as tradespeople (carpenters, thackers, etc.) to give them a reason for being there. Consider using basic animal hand puppets in the forest scenes, and assign additional ensemble members to those characters. You'll be developing new skills for those actors in the process of filling out your show. Hope this helps. - Sean