Heading South West

Heading SouthWest is an ultra-cycling adventure across Portugal that’s more about the journey than the competition. It’s not a race—every rider takes it on self-supported, with no drafting and no outside help beyond what you can find on the road. The rules are simple: you carry what you need, stop where you want, and manage everything yourself, though in the Touring category you’re free to share the ride and help each other out.

The 2026 edition covers around 1,000 km with nearly 20,000 meters of climbing, giving riders six days to make it from start to finish. Both the departure and arrival are set in Guarda, one of Portugal’s highest cities, which sets the tone right from the beginning.

Heading SouthWest is as much a test of endurance as it is a celebration of freedom on the bike. It’s long days, quiet roads, and the shared understanding between riders that the challenge is yours alone—but the experience is something everyone out there carries together.