Wandering is an innovative web-based platform that was designed to facilitate outdoor, authentic, and interactive learning via the creation of location-based interactive learning objects (LILOs). Wandering was integrated as part of a novel environmental education program among middle school students. This paper describes the Wandering platform's structural architecture and an evaluation study that was conducted among grade nine students (N = 102) who participated in the innovative educational program. Our goal was to examine students' learning outcomes and experiences while creating LILOs' and providing comments. Findings indicated high motivation among students to use Wandering, not only for completing their school assignment, but also for contributing to the community. Despite the fact that the tagging and commenting tools could have been used more efficiently by students, more than one third of the LILOs received an excellent grad. In addition, our findings indicated that Wandering is a good platform for enhancing 21st century skills, including: engagement with others, personalization, control release, and change adaption. (Contains 6 figures and 3 tables.)