Heading SouthWest

Heading SouthWest is not a race, and its organisers say so plainly. There are no medals, no podiums and no outside help. You ride with what you carry and buy what you need along the way. You may ride in company and share tools with other riders, but drafting is not allowed. Finishing times are kept only for reference, and the guidelines welcome both the riders chasing the clock and those who stop to take in the country, under the motto that slow is okay. The event says it takes its spirit from Mike Hall's Transcontinental and the Mountain Races.

The 2027 edition finally lives up to its name. It starts in Trás-os-Montes, the remote northeastern corner of Portugal, and runs diagonally to Cape São Vicente at Sagres. The organisers built the route around geographer Orlando Ribeiro's idea of Portugal as a meeting of Atlantic and Mediterranean influences. Riders pass from granite to schist, through the terraced vineyards of the Douro Valley and over the Serra da Estrela, then across the cork and holm oak country of the Alentejo before the cliffs of the Costa Vicentina. The new Travessia Nacional is the gravel option, designed and tested for gravel bikes on rural tracks, forgotten roads and old farm paths. It shares crossing points and overnight spots with the road route.

Behind it is ACAN, a non-profit association that also runs Gravel Birds in the Alentejo and has helped grow the Portuguese ultracycling and bikepacking scene since the first Heading SouthWest in 2022. The entry fee is deliberately kept low. The association works to bring riders and their spending to inland regions that have been left behind, and asks riders to leave no trace.