The chapter discusses how ICT can be used to enhance the understanding of the relationship between space, users and social practices. As an example of possible use of ICT for capturing and better understanding user’s needs, the new digital tool WAY Cyberparks is presented and discussed. A “cyberpark” is defined as a new type of urban landscape where nature and ICTs blend together to generate hybrid experiences and enhance quality of life. The WAY Cyberparks digital tool consists of a smart phone application, server/cloud and web services. Through the experiences from testing it in selected urban open spaces in Barcelona, Lisbon and Ljubljana opportunities are presented and lessons are drawn about relevant aspects of the ICT towards building a more participatory and collaborative process in planning of public spaces. A relevant aspect of the ICT lays in their ability to enhance communication with (potential) users, transforming the production of public open spaces into an interactive process, and enabling creative community participation and empowerment. Furthermore, some challenges of the increasing penetration of digital technologies devices (smart phones, smart watches, tablets, etc.) within the broader context of their use in public urban open spaces such as parks, gardens, squares, plazas are discussed, together with the consequences of this interweaving, which is growing at a rapid pace, unfolds research needs in the future.