The frequency of trips outdoors is a strong indicator of older adults’ physical activity levels. This qualitative study compared and contrasted determinants of trips outdoors between rural- (n = 13) and urban-living (n = 15) people aged 65 and older living in England. Interview transcripts were analyzed through directed and summative content analysis employing the Ecological Model framework. Some personal-level determinants (age-related barriers) and environment-level factors (car dependence, bus services) were shared across samples. The main differences were seen in how a community-based social network instigated trips outdoors for rural participants while family ties mostly led to trips outdoors for urban-living participants. Urban participants used and valued recreational facilities, but rural participants did not report them as important in determining trips outdoors. Strategies to improve public transport and minimize age-related barriers may translate from urban to rural contexts. However, social and/or physical environment interventions could be more effective if they were rural-grounded, not urban-translated.