Transforming car-oriented streets into functional public spaces and pedestrianised environments have typically been undervalued in conventional transportation, planning, and health literature. Yet urban regeneration initiatives have the potential to create environments that support active transport (e.g., walking and cycling), social interaction, and economic development. There is very little evidence-based research, however, around pedestrianisation. Few international studies have examined the association between pedestrianisation with health, social and economic outcomes from a stakeholder perspective, and there was a dearth of evidence in the New Zealand context. Limited knowledge also existed regarding the similarities and differences in attitudes toward pedestrianisation for key stakeholders, and how this impacted on the urban planning process. As such, the aims of this thesis were to determine: 1) who the users were, how they travelled, and how much money they spent in the Takapuna shopping precinct; 2) how the spending habits and travel behaviours of adult shoppers may be influenced by pedestrianisation in Takapuna’s shopping precinct; and 3) the shopper, retailer, and local government attitudes and behaviours toward pedestrianisation in Takapuna’s shopping precinct. A comprehensive literature review formed the theoretical framework for the following two research chapters (Study 1 and 2), where data was gathered from face-to-face surveys and semi-structured interviews using adults drawn from the Takapuna shopping precinct. In Study 1, a total of 325 shoppers and 62 retailers participated in a cross-sectional survey between May and June 2009. The majority of shoppers accessed the shopping precinct by motorised transport (65.8%). The main finding of this study is although median spend per trip was similar for shoppers across all transport modes ($20.00 per trip), those who actively transported to the shopping precinct visited the area more frequently than shoppers who travelled by automobile (median 12 versus 6 trips per month, respectively; p-value = 0.032). This resulted in shoppers using active transport modes spending more money in total than shoppers who travelled to the precinct by motorised transport. Shoppers reported a more negative perception of the shopping precinct when compared with retailers’ perceptions. Retailers’ perceptions of shopper mode of transport to the area, perceptions of traffic flow, and pedestrian access were similar to those reported by shoppers. Subsequent changes to the urban environment that support the increased use of active transport modes may enhance economic development through increased purchasing frequency and provide public health benefits through greater accumulation of physical activity. Study 2 investigated the perceived benefits of pedestrianising the shopping precinct in Takapuna, Auckland with key stakeholders. Semi-structured interviews were conducted with nine stakeholders drawn from three groups: shoppers, retailers, and local government. Shoppers and retailers perceived pedestrianisation schemes as a way of improving aesthetics, connectivity and accessibility, safety, public transport infrastructure, and walking and cycling levels within the area. Retailers were concerned about the impact of short-term construction on retail revenue. Local government respondents realised the potential of pedestrianising the area to improve existing infrastructure and to become more economically competitive with other nearby retail options. All stakeholders recognised the importance and benefit of securing collaborative input into urban regeneration schemes, and identified that the initiatives must be considered within a long-term cohesive strategic framework. This research adds to the growing body of urban regeneration research by identifying associations with physical activity and economic outcomes, and substantially contributes to the knowledge base within the New Zealand context. The evidence presented in this thesis supports that changes to the urban environment that support pedestrianisation in shopping precincts will likely provide long-term benefits, namely greater economic spend within the area and opportunities to accumulate physical activity.