I bought a trail-a-bike the other day and I loved it. Riding tandem takes a little getting used to, but if your son ENJOYS riding a bike, he could love it (plus he could learn road safety skills from you)! The trailer disattaches and folds down really easily so you could leave the bike with him at school...could he take it on the bus to the Boys Club?? Then you could pick him--and the bike--up at the Boys Club, reattach the trailer, and ride home together....