The Council of Machico is one of the places where we have more trail courses for all kinds of training.
One reference in this area is the Training courses of the parish of Porto da Cruz with several courses for you to try since the easiest of 9km to the very technical of 35km. Due to the work of the local club Ludens Clube de Machico (one of the oldest in Madeira in terms of Trail Organizations) there is also lots of other nice tracks around this council.
Therefore in Machico you have a lot to choose from, since some nice trail with less gap in the parish of Caniçal to the one very challenging in Porto da Cruz. For a easy one we recommend the one of Ponta de São Lourenço, to the more experience traillers try the amazing climb of "Lombinho" and descend of the "Degolada" both in Porto da Cruz.
Being in Machico, you have several options to small and fast training or real endurance trails, all circular track that you can take right from the city center, but especially in Porto da Cruz, or the high mountains in Poiso/Chão das Feiteiras/Ribeiro-Frio.
Vídeo of the trail of Risco - Larano: