I'm trying something new this Advent. I'm trying to have a 'family Rosary' each night. We've managed it for three nights now - but I'm doubtful that we'll really be able to do it every night. Sometimes, with various commitments, we're all just not in the house together long enough in the evening to make it work.
I've found that one of the best resources for saying the Rosary with children is this site. They have wonderful meditations for each of the mysteries - written specifically for children - and broken down so that there is a sentence read before each Hail Mary. Go here for an example of the Joyful Mysteries.
I love it because it is so much easier to meditate on the mystery one sentence at a time. This allows us to stay more focused and not have our minds wander to unrelated subjects when we get to the middle of the Hail Marys.
We take turns reading the sentences before each Hail Mary - it helps everyone to stay involved in the process as well. Harry's been a little reluctant to do this - and although he didn't actually use his rosary today - he did stay in the room and he did say the prayers - so that counts as involved if you ask me.