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Maine lends itself to many outdoor activities with its varied geography. Many communities around the state have acknowledged this asset and designed trail systems that allow for people to experience the outdoors. In Maine, many trail organizations are nonprofits as it allows them to provide critical services that contribute to economic stability and mobility in surrounding communities without being dependent on local governments (National Council of Nonprofits 2019a). The nonprofit community in Maine has been successful throughout the years in creating a robust and vibrant community of citizens that help protect the environment, educate children, and inform the government (Maine Association of Nonprofits 2019b). Lewiston/Auburn Trails (L/A Trails) was founded in 2001 with the goal of providing the community with safe places to enjoy nature. Originally, L/A Trails was an independent nonprofit organization. They raised funds to complete crucial projects such as installing lighting in Railroad Park and Mount Apatite Park. In 2007, L/A Trails joined the Androscoggin Land Trust (ALT) in the hopes of developing an accessible and frequented trail system which would later connect to the Maine Greenway. However, ALT began to focus its time and resources on other projects, causing L/A Trails to separate from ALT and become an independent organization (Androscoggin Land Trust, 2019). Despite this change, their end goal will remain the same: creating green spaces in the L/A area that connects and positively impacts the community. It is their hope that the trails will be seen as an asset and a source of pride for the community. L/A Trails’ goal is to provide public green spaces through trail access in Lewiston and Auburn. In this report we assess five different possible structures for L/A Trails to become an independent organization which include: private foundation, private operating foundation, limited liability company, fiscal sponsorship, and public charity. By synthesizing information from governmental sources and reports from organizations doing similar projects, we identify the different elements that make up each structure and compare and contrast them using a chart and scoring system. After calculating the results, we determine that the best fit for L/A Trails was to become a 501(c)(3) public charity. For the final part of this report, we explain how the different elements of this structure are intertwined with the goals of L/A Trails and how it can maximize their efforts. We then detail a nine-step comprehensive plan for L/A Trails to become a public charity in the state of Maine. Finally, by interviewing representatives from other small trail organizations we were able to distinguish and organize some recommendations on how to form and ensure the longevity of the new organization.