Calheta was not one of the most famous place for trail running lovers in Madeira, that usually prefer the north cost of the island for training. Also most of the competition in Madeira were organized in the north cost, but since the organization of the first Trail da Calheta by the Clube Montanha do Funchal, the madeiran trailers start to look differently to this location in the south of the island.
There is several trails that provide diversified training, but maybe the most challenging are the "caminho real" (royal road) the connects Paul do Mar to Prazeres, just next to the Hotel Jardins do Atlantico. This course with less than 5km has being used for several competitions of Vertical KM (in the case 1/2 vertical km) and is a great option for short trains but with high positive gap.
The I Trail da Calheta really was a surprise and reveled great track in this council that are as beautiful as demanding, especially the climb from Paul do Mar till he viewpoint of Raposeira, a course to do with great respect and special attention to the heat that is normal around this area.
One other parish with lots os potential for trail running is Ponta do Pargo, still a bit unexplored but with nice track at a average 500m from the sea level.