The increasing nuclearization of Japanese urban families has left young homemaking mothers often feeling isolated and vulnerable to the stresses of childrearing. Many of these parents welcome venturing from the house for some diversion and social interaction, making it doubly important for society to create outdoor environments that support going out with small children. The present study discusses a questionnaire survey comparing young mothers' habitual outings in four Tokyo neighborhoods-one long-established and one newly developed residential area each from the largely white-collar yamanote district to the west and the traditionally more commercial shitamachi district to the east. Respondents set down destinations, purposes, time required, and means of travel on a time sequence chart and recorded routes on a map. In all areas, the most popular destinations were the supermarket and city park. Residents of the new neighborhoods, however, headed to larger parks and shopping complexes, while in the older shitamachi neighborhood, respondents frequently patronized small shopping streets where they could enjoy talking with shopkeepers. Routes were typically selected according to functional considerations such as traffic safety and smoothness of the paving, a concern particularly for stroller users. Wide sidewalks were preferred because the mothers could walk side by side with friends while chatting. At the same time, recreational criteria were also cited, including the presence of roadside greenery, running water, or objects and people stimulating to the children. The older neighborhoods had more routes satisfying recreational needs than the newly developed ones, which in turn were better at answering functional needs. The results highlight that attempts to design outdoor environments for parents with small children need to address not only safety and accessibility, but also the demand for stimulation and company.