Episodic memory, future thinking, and memory for scenes have all been proposed to rely on the hippocampus, and evidence suggests that these all decline in healthy aging. Despite this age-related memory decline, studies examining the effects of context reinstatement on episodic memory have demonstrated that reinstating elements of the encoding context of an event leads to better memory retrieval in both younger and older adults. The current study was designed to test whether more familiar, real-world contexts, such as locations that participants visited often, would improve the detail richness and vividness of memory for scenes, autobiographical events, and imagination of future events in young and older adults. The predicted age-related decline in internal details across all 3 conditions was accompanied by persistent effects of contextual familiarity, in which a more familiar spatial context led to increased detail and vividness of remembered scenes, autobiographical events, and, to some extent, imagined future events. This study demonstrates that autobiographical memory, imagination of the future, and scene memory are similarly affected by aging, and all benefit from being associated with more familiar (real-world) contexts, illustrating the stability of contextual reinstatement effects on memory throughout the life span.