This article tries to search for interconnections between three different approaches to outdoor activities. These approaches are the sportive, the poetical and the philosophical. The first part deals with the meaningfulness of this concept. Heidegger´s analysis of Trakl´s poem Winter Evening gives some possibilities how to interconnect philosophy and poetry. The spiritual dimension of man is enlarged by poetry in a way that is inaccessible for science or philosophy. The author follows Heidegger´s analysis of Georg Trakl´s poetry. He develops his ideas and focuses them on the topic of outdoor activities. The selected part of Hölderlin´s poem In Lovely Blue is presented here as the motive to do outdoor activities. Then some examples from the production of Czech folk singers are added and discussed. Extreme moments arising from some difficult life situations are illustrated by a selected example – a story about two mountaineers. The author touches ethical discourses and confronts theory with practice. He shows that responsibility for decision making can be enlarged by the complexity of our perception of the world. An ideal model of an “outdoor being“ is presented in conclusion – one who should carry a bit of a philosopher, a poet and a sportsman/woman altogether in his/her mind.