Land trusts often seek to increase public access to conserved lands through trails. But whether a site already has existing trails, or if new trails are proposed, maintenance and implementation challenges are common. The importance of a comprehensive assessment and planning process cannot be understated, and the consequences of poor planning include trials that are costly to maintain, dangerous for users, and cause environmental harm to the landscapes they traverse. So where can you start to assess and plan for a trail system that is sustainable, accessible, and doesn’t conflict with conservation goals? This workshop will outline the assessment and planning process, sharing considerations and tools that can be used by small and large land trusts (and even by volunteers!) alike to ensure that they know what to expect and can take an active role in creating functional trails and trail systems on conserved lands.