Montemor-o-Novo is situated just an hour outside of Lisbon by car. The town itself is as charming as it is unpretentious, built around a small park at its nucleus and a rather impressive public pool (as it can get very hot in the summer) nearby. There are plenty of cute spots to duck in out of the sun to grab a cold drink and a smattering of local Alentejano dishes, and a few places to stop and shop for a picnic or to stock the cooler in your car should that be your thing.
Aside from modern-day conveniences, the municipality boasts a whopping 12 prehistoric monuments like the Escoural cave paintings and the dolman chapel of São Brissos (converted from a doleman to a chapel in the 17th century). Most of these monuments require a little hide-and-seek to find them.
The most stunning site in the area, however, is in plain view. Looking over the town on a picture-perfect hilltop are the rather haunting ruins of the13th-century medieval castle of Montemor-o-Novo. Once inhabited by the rich noblemen and regal monarchs, the fortification of the impressive citadel was comprised of long walls, a Gothic clock tower, and an elegant central tower curiously named, the Torre da Má Hora (Tower of the Bad Hour), and at least three gateways.
Bits and pieces of these are still standing after it fell out of use in the 16th century and exploring them in their current state is both charming and alarming.
The guardhouse near the entrance dates back to around the 16th century. Look up and you’ll see King Manuel I’s coat of arms above the door. Once through the gates you’ll find the small 1300s church of São Tiago with its charming interior frescoes. There you’ll find a modest amount of information about the ancient origins of the site and a few stories about some significant events that went on here. For example, in 1495 under Dom João II, this is where the plans for Vasco da Gama’s voyage to India were drawn.
It’s free to enter the site, but remember, if it’s the summer, protect yourself from the incredible heat of the sun and remember to bring some water as well. Since the area is in ruins, exercise caution around the structures, even if you’re just jumping from shadow to shadow to keep cool. Several modern fire towers have been built on the site to watch for any smoke on the horizon, so if you plan to light up, please be careful. This area is prone to fires.
Foodie Tip: If you’re a little hungry after your tour of the ruins, we recommend checking out Wine Bar Tapas e Mariscos and going for the polvo (octopus) and the pica pau (beef strips with pickled carrots and cauliflower). You can sit outside at the comfy wooden picnic tables or opt for the charming interior, decorated with old wine barrels and softly lit by modern hanging paper lanterns.