A circular tour, where archaeological remains are in evidence. A visit to the castles of Évoramonte and Arraiolos completes this itinerary through history and heritage.
To begin this journey, nothing better than to climb the walls of the medieval castle of Montemor. You can do so by the dirty path that goes from near Rotunda da Chave, south of Montemor, where you have the roads to Alcácer/Torrão and to Escoural/Aljustrel. Or by the sidewalk that goes up on the opposite side, from near the bullring. From the summit, a vast panorama is covered, including the disabled railway viaduct leading to the Torre da Gadanha, which can be a good guideline for a fun and adventurous walk. Keep in mind that you risk to find bushes, fences and mud during the ride. But for those who have the spirit for adventure, this will begin as soon as you cross the viaduct by a very narrow lateral walkway...
Quit Montemor southward to Alcacer / Aljustrel, passing the bridge over the Almansor river to the aforementioned Rotunda da Chave. Take EN2 south towards Santiago do Escoural. This town is extensive and friendly and has, in addition to a fairly famous restaurant, another attraction: the caves with prehistoric paintings, inhabited since the most ancient times. It is here that you should leave this road that - you may not know it - is the largest Portuguese road, starting in Chaves and ending in Sao Bras de Alportel. Go to the left by a side road that will take you via São Brissos, Valverde and Nossa Senhora de Guadalupe.
In São Brissos see a curious anta-chapel, symbolizing the Christianization of the ancient places of worship, while in the vicinity of Valverde you may see the dolmen Zambujeiro, one of the best testimonies to the strength that the megalithic civilization had here, 5000 years before Christ. In Nossa Senhora de Guadalupe and meeting the road-Montemor Évora (EN114) you may find an excuse to visit another vestige of the same era: the Cromlech of Almendres. Arriving in Evora is still time to see or revisit this city, which historic center has been classified by UNESCO. The best is to leave the car outside the walls and have a walk around by some of Évora icons as the Giraldo Square, the Cathedral and the Igreja de São Francisco and then the Teatro de Resende Gracia and the Roman temple.
On the road again, take the direction of Estremoz and pay attention to the speed limits and hidden speed cameras, very frequent in this road as, indeed, across the Alentejo. The EN18 gives access to Évoramonte, which castle you start to see from a distance. It is a curious construction, representing the transition from the medieval castle to the fortification with ramparts adapted to the use of artillery. As an evidence of this, the towers erected in the four corners and several lines of fire for artillery installed in a low level. Again it is worth leaving the car down here and start walking to discover the castle and the picturesque villages surrounding it. In a house neighboring the walls, it was signed in 1834, the agreement that ended the civil war between liberals and absolutists and formalized the latter's defeat and the exile of King Miguel.
Leave the road that leads to Estremoz, turning onto the left to the secondary road leading directly to Vimieiro, at the junction with the road Elvas-Montemor, the EN4. Arraiolos is the last major leg of this trip, now in its return phase. Once again the medieval castle is visible from afar. If you enter through Porta da Vila, located further south, just to the right you will have the Manueline clock tower. On the other side, the last stronghold of the medieval fortress. The parade ground was surrounded by five towers, of which only three remain, including the keep. To the west, the Porta de of Santarem, with its gothic arch and two square towers. From the summit, there is much scenery to see, noting that, especially to the north, towards Pavia, the terrain is fairly undulating, with lots of hills covered with olive trees. Do not go here without peeking the famous carpets that gained fame in Portugal and abroad. It remains now to resume EN4, and continue to Montemor-o-Novo, the end of this tour through lands of the Alentejo.
Access: By A6 or EN4, until Montemor-o-Novo.
To have into account: If you enjoy walking, you can take the platform of the old railway that joined the Alentejo Line in Torre da Gadanha (12 km distance), starting from the old station and followed by the metal bridge over the river Almansor, but you will find fences and other obstacles in your way.
Length: Some 100 km.
Meals: Manuel da Azinheirinha (T. 266 857 504), in Santiago do Escoural, O Escondidinho (T. 266 892 366), in Montemor-o-Novo.
Other spots to visit: Estremoz, Pavia, Brotas, Avis.