THE ROUTE(S)

nature -- culture -- adventure

The routes of Heading SouthWest cross some of the most remote, isolated, and challenging territories in Portugal. The routes are designed for a true bikepacking and adventure cycling experience. Heading SouthWest is much more than a long-distance ride — it is an environmental and sociocultural journey, deeply connected with the landscapes, traditions, and people of Center and North of Portugal.

In 2026, Heading SouthWest will feature two routes: HSW 500 and HSW 100. All start and finish in the city of Guarda.

HSW 500 is the smaller and more accessible version, forming a shorter loop and sharing much of its course with the larger route. HSW 500 avoids the harshness of the Northeast of Portugal, but challenges riders in the Douro Valley and Serra da Estrela. HSW 500 has an elevation gain of 10,000 meters. Designed as an introduction to bikepacking and for a more relaxed adventure. Touring is the only category available — meaning all riders can help each other and ride together.

HSW 1000 is our traditional distance route. Heading SouthWest has played a pioneering role in the development of the bikepacking and ultracycling scene in Portugal: it was the first established bikepacking and ultracycling event in the country. It shares a strong connection with the principles of self supported long distance cycling, inheriting the philosophy of Mike Hall's Transcontinental. HSW 1000 was designed to be an epic experience and a tribute to road cycling, with endless remote roads and strong presence of sociocultural elements. And of course, promoting the connection with nature.

historic villages of portugal in the border

Where it all begins. The Historical Villages of Portugal (Aldeias Históricas de Portugal) is a network of 12 villages, most located in the central Portuguese region of Beira Interior. These villages are preserved for their historic and cultural significance, as they were strategically important border defenses and played a vital role in the country's formation. The routes cross will cross some of them. Highlights to Almeida, Castelo Rodrigo, Sortelha and Trancoso.

Route(s): HSW 1000, HSW 500.

Trás-os-montes and montesinho nature park

Trás-os-Montes - literally meaning in English "behind the mountains". This region is landlocked by the Douro and Tâmega valleys to South and West and by Spain to the North and East. This relative isolation has led to the survival of cultural traditions that mark the Portuguese identity. The most emblematic example are the Carnival and Pagan figures of many villages, such Podence and Varge. It is also the home of the Mirandese culture and Portugal's second official language.

Route(s): HSW 1000.

tua valley regional and nature park

One of Portugal's hidden gems, as well as a pleasant surprising as a road cycling destination - even for the national community. This territory features a diverse landscape of mountains, plateaus, and steep valleys carved by the Tua River. Although not as famous as its neighbor the Douro Valley, its views are just as spectacular, if not more so. We introduced the Tua Valley in the past edition and we didn't hesitated to add it again to the HSW'26 route.

Route(s): HSW 1000.

Douro valley - unesco world heritage site

The Douro Valley is a designated UNESCO World Heritage Site due to its stunning cultural landscape, which is a result of over 2,000 years of winemaking. It is the world's oldest demarcated wine region, famous for producing Porto wine. Its terraced vineyards, charming villages, and the Douro River create a unique and beautiful scenery shaped by both nature and human effort, that our adventurers will experience.

Route(s): HSW 1000, HSW 500.

serra da estrela unesco global geopark

Serra da Estrela is the highest mountain range in mainland Portugal. It is home to the country's highest point, Torre, a peak on a plateau, located at approximately 2,000 meters above sea level. Estrela will be the the setting for an epic finale in the Heading SouthWest experience: climbing all the way up to Torre before rolling back into Guarda. Serra da Estrela is also a designated UNESCO Global Geopark and the most emblematic national territory for road cycling.

Route(s): HSW 1000, HSW 500.