Community wayfinding becomes more challenging with age and decrements in functioning. Given the growth in numbers of older adults, we need to understand features that facilitate or inhibit wayfinding in outdoor settings to enhance mobility and community engagement. This exploratory study of 35 short- (n = 14) and long-term (n = 21) residents in an ethnically diverse neighborhood identified relevant wayfinding factors. Data collection included an interview, map-drawing task, and walk along a previously audited, prescribed route to identify key wayfinding strategies. Most participants sought information from other people as a primary method of route planning. Street signs and landmarks were overwhelming favorites as helpful wayfinding features. When asked to recall the route following the walk, only half of participants gave completely correct directions. Findings reinforce the importance of landmarks and legible, systematic, and consistently available signage, as well as trustworthy person-to-person information sources. Findings also underscore the need for wayfinding research in diverse environments.