Most agree that school-based physical education is one of the few settings responsible for promoting lifetime physical activity for all children. However, physical education teachers' reliance on traditional team sports does not match adult activity habits and therefore may not increase the chances that children will pursue a lifetime of physical activity participation. This article offers insights and lessons from 10 teachers who offer outdoor pursuits (OP). These teachers found OP activities to be beneficial for students and believe they have more realistic connections to lifetime activity habits than traditional team sport. They also find teaching OP to be both personally and professionally rewarding. That said, this article also presents some of the challenges these teachers face when delivering an OP curriculum.