Several recent studies have explored the effect of contextual familiarity on remembered and imagined events. The aim of this study was to examine the extent of this effect by comparing the effect of cuing spatial memories, episodic memories, and imagined future events with spatial contextual cues of varying levels of familiarity. We used real-world landmark cues that had all been previously visited by the participants, and we measured the retrieval time, detail-richness, and vividness of remembered scenes, events, and imagined future events based on these cues. Participants consistently rated scenes and events based on more familiar cues as more detailed and more vivid, and they took less time to retrieve them. When the types of details were examined, it was revealed that the effects of increased contextual familiarity carry over to non-spatial details in the case of remembered events but possibly not in imagined events. This study provides evidence regarding how episodic memory and imagination are reliant on spatial context and possibly the process of scene construction.