This paper evaluates the occurrence of stay activities such as sitting and children’s play in two neighborhood shopping streets in the Tokyo Metropolitan area through direct observation and mapping. Results reveal the dominance of mobility on weekdays with cars, the rarity of stay activities on ordinary car-free Sundays, and the upsurge of stay activities during organized street events. Finally, the study discusses the key trends in the occurrence of stay activities, the significance of organized activities such as playstreet and music performances, innovative use of street elements, and the influence of adjacent stores on the liveliness of the streets.