The lack of physical exercise is among the most relevant factors in developing health issues, and strategies to incentivize active lifestyles are key to preventing these issues. The PLEINAIR project developed a framework for creating outdoor park equipment, exploiting the IoT paradigm to build “Outdoor Smart Objects” (OSO) for making physical activity more appealing and rewarding to a broad range of users, regardless of their age and fitness. This paper presents the design and implementation of a prominent demonstrator of the OSO concept, consisting of a smart, sensitive flooring, based on anti-trauma floors commonly found in kids playgrounds. The floor is equipped with pressure sensors (piezoresistors) and visual feedback (LED-strips), to offer an enhanced, interactive and personalized user experience. OSOs exploit distributed intelligence and are connected to the Cloud infrastructure by using a MQTT protocol; apps have then been developed for interacting with the PLEINAIR system. Although simple in its general concept, several challenges must be faced, related to the application range (which called for high pressure sensitivity) and the scalability of the approach (requiring to implement a hierarchical system architecture). Some prototypes were fabricated and tested in a public environment, providing positive feedback to both the technical design and the concept validation.