The partnership between After School Matters, Free Spirit Media, and West Town Bikes will support teens in West Town and Humboldt Park communities to develop identities as advocates and community leaders on alternative transportation. Free Spirit Media youth will engage as peer leaders as digital media support for high school teen apprentices at West Town Bikes, who are deeply committed to utilizing and promoting skateboarding and bicycling as alternative transportation modes. This year, the Trust for Public Land is leading the charge for the development of “606,” a 20-acre park and trail system featuring an elevated linear park that will connect four disparate neighborhoods identified by the City as “park poor” – Bucktown, Wicker Park, Logan Square, and Humboldt Park. This park system will directly impact teen skateboarders and bikers; the apprentices at West Town Bikes will therefore engage with the community, park personnel, and other stakeholders to bring youth voice to the conversation. Free Spirit Media will share their expertise on social media engagement and advocacy with West Town Bikes, broadening the impact of their existing tools and social media workshops. High school interns who are honing their professional and technical skills in media production will document the experiences and stories of their peers as they collect data on bike safety in the neighborhood, lead workshops for the public, and advocate for infrastructure that supports teen skating and biking.