Most previous studies on time perception have examinedtemporal order and distance judgments in isolation usingcontrolled stimuli. However, in real life, these two elementarytemporal experiences are related. Here, we examine the effectsof age and event structure on temporal estimation and introducea novel timeline estimation paradigm comprising temporalorder and distance judgments with naturalistic stimuli. In twoexperiments, we asked participants to view a three-minute-longvideo clip and mark the temporal order and distance of aspecific scene of the video on a horizontal timeline. In the firstexperiment, we conducted the timeline estimation task withthree different age groups – 6-8-year-olds, 9-11-year-olds andadults – and found age-related differences in the participants’accuracy and variability of temporal estimation. Thenonlinearity between their estimates and stimulus distancedecreased as their ages increased. In Experiment 2, we testedthe effect of event structure on participants’ timeline estimationand observed that more complicated video resulted in moredistorted temporal estimation. In sum, the current studycorroborated the timeline estimation task to be a valuable toolfor assessing temporal judgments across development.