In the second century BC the settlement is said to have resisted a Roman siege for seven years. This feat is the origin of the Festival of the Crosses, which the village celebrates on May 3rd every year.

In the 12th century, D. Afonso Henriques donated the settlement (which had been captured from the Moors) to the Order of the Templars, whose Master in Portugal, Gualdim Pais, ordered the castle to be rebuilt. The village, which is spread over the hillside, boasts one of the most interesting landscapes in Portugal. Granite boulders are used as walls for the houses, and in some cases roofs consist of a single block of stone - which is why the houses here are said to have "only one tile".

Added interest is provided by several large, emblazoned houses, Manueline doorways and the house where the doctor and author Fernando Namora lived, practised and found inspiration for his novel ‘Fragments of a Doctor’s Life’.

Those who feel energetic enough to make the climb up to the castle are rewarded with one of the most stunning views in the region. The bold knights of the Christian Reconquest were buried in hollowed out rocks in this stronghold.

However, perhaps the most important place in the village is Lucan’s Tower. Dating back to the 14th century, the tower is crowned with a silver cockerel, a trophy awarded to Monsanto in a competition in 1938 in which it was judged to be the most Portuguese village in Portugal.