This small hilltop town of Monsaraz used to help guard against the Spanish a section of the River Guadiana. The town came to prominence when it was captured from the Moors in 1167 by the famous soldier Geraldo Sem-Pavor (the Fearless).
He then set about improving its fortifications and then gave the castle and village to the military Templar Order. It continued to suffer later many attacks from the invading Spanish throughout the following centuries. However, it was sacked in 1381 by the Earl of Cambridge when his proposed marriage to the daughter of Dom Fernando I was annulled and as a result he unleashed his anger on the town.
His manner of gaining easy entry into the almost unassailable castle can be suspected as having pretended to still having enjoyed the favours of the Portuguese King. Later, in 1385 Don Juan of Austria with Spanish forces seized the castle in a surprise attack.
Perched on the top of a hill, this little known small town is a “jewel in the crown” of the Alentejo, if not Portugal itself. It is a small walled group of dwellings that carefully preserve most of their original charm by retaining the old exteriors and the original quaint slated streets.
The inhabitants of the town take particular pride in maintaining its somewhat medieval atmosphere with its few narrow streets that are in parts are quite steep as they fall away to the defending walls. The views from its 13th Century castle walls are panoramic over both the plains of the Alentejo, the waters of the new Dam and views towards the Spanish boarder.
The courtyard of the Keep of the Castle has now been adapted and is used as an occasional Bullring whilst the viewing spectators line the castle walls. In the Igreja de Santa Maria da Lagoa is the 13th Century tomb of Gomes Martins Anes, the first Lord of the town.
During the autumn many neighbouring villages in this region use or create a temporary makeshift Bullring as an opportunity for the "local young bloods” to chance their courage. Without any special protection or weapon, they pitch their skill against the charge of the younger bulls that are progressively increased in weight and age during the event.
In the surrounding area of Monsaraz are several fascinating megalith and dolman monuments that are comparatively easy to find as they are mainly sign posted at the side of the road with the word “Anta”. These symbolic remains date back to between 4.000 and 2.000 years BC.
Over 130 sites have been recorded in the surrounding countryside but some have been re-located due to a massive Dam that has been built. Several interesting sites are now under water including the small quaint village of Luz with its Roman ruined fort.
About 16 Kilometres to the west is the now major town of Reguengos de Monsaraz, a centre for this grape growing area. A specialty of the town is “Bolo Rançoso” that is made with pumpkin filling.
Some 4 Kilometres to the south is another small town of Mourão that has the impressive high walls of a 14th Century castle overlooking the River Guadiana. Much further to the south is the town of Moura, a name said to have been given to it in memory of the beautiful daughter of a the Moorish governor who threw herself from the tower of the castle after learning her lover had been killed in battle.
A siege in 1657 destroyed most of the castle and what was left was virtually blown up by the Spanish in 1707. The church of Nossa Senhora do Carmo that is located near the castle was founded in 1251 as the first Carmelite Convent in Portugal. To the west of this town is the Spa Águas de Pisões.
To the north of Monsaraz is the town of Redondo set in the heart of the vine growing district. This area also has many megalithic monuments indicating the regions popularity during the Neolithic period. There is still some evidence left of its castle built by Dom Dinis in the 14th Century.
Also to the north is the town of Alandroal, an established fortified town from the 14th Century. The nearby 16th Century Erminda de São Bento was built to record the towns gratitude from being apparently saved from the various plagues that swept Europe and that always seemed to avoid this particular town.
At the small small town of Terena is the Sanctuary of Nossa Senhora da Assunção da Boa Nova which dates back to the 14th Century. It is considered to be one of the most historic monuments in the Alentejo.
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