The technological innovations of the last decade have caused countless changes to everyone's lifestyle, especially in the number of hours spent in front of a screen. These generational differences are even more marked if the new generations of students are taken into consideration, in fact, even at the school level, technological innovations have brought changes. Just as lifestyle and teaching have changed, what is considered as the "needs" of pupils and how they live and relate both in formal and informal environments have also changed. Considering the emergency period caused by the COVID-19 pandemic, greater attention has been paid to the importance of exercising and everyone has also re-evaluated the beauty and benefits of exercising outdoors. Outdoor Movement Education in this sense can be a key that allows the new generations to experience the emotions and sensations that can be felt during outdoor moving activities. This work is a reflection on how technology can be a tool to increase the benefits in Outdoor Movement Education considering children and youth with special needs. The results of this work have shown how the use of technology in Outdoor Movement Education brings numerous advantages both under the didactic profile (i.e., life skills) and with regard to the cognitive (i.e., attention and concentration), motor (i.e., motor skills, fundamental movement skills) and affective (i.e., enjoyment) domains of learning respectively.