In a picture-book scene of hills with a light mantle of cork oak trees sits Montemor-o-Novo. It’s an unpretentious town In the middle of the Alentejo countryside, and has a few heavyweight sights to circle on your map. Alentejo is strewn with prehistoric monuments, and there are 12 in this municipality alone.
One dolmen was even adapted into a chapel in the 17th century, while there are rock paintings in the Escoural Cave here. Montemor-o-Novo’s medieval castle reigns over the town and has ruins and views that stop even the most jaded tourists in their tracks.
Let’s explore the best things to do in Montemor-o-Novo:
1. Castelo de Montemor-o-novo
At the town’s castle are traces of three gates, the remnants of the cistern, long sections of the walls and a Gothic bell tower.
There’s also a guardhouse from around the 16th century, with the coat of arms of King Manuel I above the door, as well as vaulting inside.
The small church of São Tiago dates to the 1300s and has an exhibition about the site, explaining its ancient origins and some of the events that took place here.
One was in 1495, when at the court of King John II plans were drawn up for Vasco da Gama’s voyage to India.
The church also has its own frescos from the 1600s and 1700s that deserve a peek.
2. Convento de Nossa Senhora da Saudação
Also within the castle walls, a few paces from the crumbling stone buildings lies a Dominican convent begun in 1502. You can make out some clues to this period, on the main entrance and the “Porta das Freiras” (Gate of the Nuns), both of which are surmounted by an armillary sphere.
This was a Manuel I’s personal symbol, glorifying Portugal’s maritime prowess.
The dormitory and church arrived in the second half of the 16th century.
In the Church the decoration is a little newer, from Portugal’s Philippine period when it came under Spanish control.
So the retable is in the style of the Royal Valladolid School, with patterned multicoloured tiles, while the lower choir shines for the frescos on its vault and green tiles on its walls.
3. Gruta do Escoural
These caves are a must-do for their prehistoric art, left during the Upper Palaeolithic, up to 10,000 years ago.
The attraction has never been easier to visit, as it was recently modernised with a new system of footbridges and an interpretation centre.
There are images of animals, mostly cattle and horses, but with some strange hybrids too.
Later, in the Neolithic period (5000-3000BC), the farming communities used the cave to bury their dead, and some of those remains can be seen in interpretation centre where there’s also a detailed analysis of the paintings.
4. Capela-Anta de São Brissos
Chances are you’ve never seen anything like this little monument in Santiago do Escoural.
The Capela-Anta de São Brissos is a chapel from the 1600s, but the special thing about it is that it was built into a 5,000-year-old dolmen, which makes up its chancel.
Standing outside it’s easy to work out which part is prehistoric as the back end of the chapel bulges out.
This section has three standing stones with a horizontal slab laid on top.
5. Ermida de Nossa Senhora da Visitação
The highest of the hills to the northeast of Montemor-o-Novo has a path climbing from the edge of town up to this little sanctuary.
The chapel is from the Manueline period towards the start of the 16th century, and there are hints of this architecture on the patterned stone portal.
The inside walls sport 18th-century tile panels with scenes from the life of Mary, and if you can get into the sacristy there are as many as 200 ex-votos left by pilgrims down the centuries.
The oldest of these is from 1799. Stay to survey the town from the hilltop and to drop by the small cafe up here next to the hermitage.
6. Igreja do Calvário
In the 1700s the small oratory that had stood since 1593 was turned into an impressive church with Baroque design, complete with a ceremonial hall for the church’s fraternity (Order of the Brotherhood Of Souls).
In the hall, now a sacristy, the walls are coated with blue and white azulejos that were painted in 1716. As for the church amid the older fittings, including a pulpit and sumptuous tile panels, there’s a 1956 painting of the passion by the eminent Azorean artist Domingos Rebelo.
7. A Tour in the Old Centre
The tourist office has drawn up a 16-stop walking tour on the Montemor-o-Novo’s web of cobblestone streets, stairways and little squares.
The street-plan hasn’t been altered since it was laid out in the Middle Ages, while the most inspiring traces you’ll catch sight of are Manueline, from the beginning of the 1500s.
Still standing are a clutch of palaces from this period, while the town’s convents are intact and easy to identify.
The route begins at the turn-of-the-century market hall, beckons you past the mansions on Rua 5. de Outubro, to the old town hall on Largo Paços do Concelho.
You’ll wander along Rua dos Almocreves where there’s a 13th-century archway to the 16th-century Hospital de Espírito Santo e Santo André.
8. Praça de Toiros de Montemor
There have been bullfights since the 1400s at the latest.
For hundreds of years these were staged in a wooden enclosure on what is now Praça Miguel Bombarda.
But in 1882 the town got this small arena, which was updated with a capacity for 3,000 at the dawn of the 20th century.
Now bullfighting isn’t everyone’s cup of tea, but if there’s some consolation it’s that even though there is a matador using bandeirilhas (small javelins) the bull is never killed in the ring.
If fancy attending, fights normally take place at the end of April and the beginning of September.
9. Convento de São Domingos
South of the old centre, on Largo Professor Dr. Banha de Andrade, is a Baroque monument with some earlier Mannerist architecture.
The 17th-cenrury polychrome tiles in the church nave and chancel are a delight.
But the reason to put this on your itinerary is to see the small museum in the convent.
Together with an assortment of liturgical art, there’s archaeology (pottery and tools) from the local prehistoric sites, and an exhibition for Montemor’s bullfighting tradition.
10. Piscina Municipal Montemor-o-Novo
You’ll understand the allure of the town’s outdoor pools when the mercury shoots above 30 in summer.
Montemor-o-Novo is an hour from the coast, and so this a good, inexpensive substitute if the younger members of the clan need somewhere cool to go nuts.
The main complex is outdoors, with a full-sized pool that has lanes for serious swimmers, and a spacious kids’ pool next to it with a slide and fountains.
Around the pools is an inviting sweep of grass where you can plant yourself under a parasol for a picnic .
11. Megalithic Route
Impressive monuments left by the area’s prehistoric inhabitants litter the countryside around Montmoro.
Including the Capela-Anta de São Brissos there are 12 to be found, and once again all have been incorporated into an itinerary.
These menhirs and dolmens are approximately 5,000 years old and date to the time of the human remains in the cave at Escoural.
If all this prehistory has piqued your interest, the greatest megalithic site in the region, and all of Portugal and Spain in fact, sits half an hour away at the Almendres Cromlech.
The monument was begun in 8,000 years ago and the archaeology shows that it was visited and altered over the next three millennia.
12. Rota do Montado
If you had to pick an image to encapsulate the Alentejo countryside, it would be an arid rise scattered with cork oaks.
These trees are never in dense copses, but instead are dotted quite sparsely on the countryside.
The patches of grass between the trees are grazed by free range pigs and cattle, and the oaks’ acorns are a staple for these black pigs that are bred for cured presunto ham.
The tourist office has a route that allows you to appreciate this quintessentially Portuguese scenery.
If you’re holidaying in a larger group you can also reserve tours of the cork factories dig a little deeper into Alentejano life.
13. Tapetes de Arraiolos
A brief car ride east and you’ll be in the town of Arraiolos, known far and wide for its hand-woven carpets.
This craft is anchored in the Moorish period, and there’s an interpretation centre in a historic former hospital to introduce you to the techniques and patterns.
Draped on the gallery walls are mind-blowing pieces of needlework, some of which decorated stately homes and others with Christian motifs for churches and convents.
There are antique looms, and most days a weaver is at the museum to show you how they’re made, even handing you the needle to try for yourself.
14. Wine Tourism
The warm climate around Montemor gives us full-bodied and very drinkable reds.
These are usually a blend of Portuguese varieties like Touriga Nacional and Touriga Franca, as well as grapes like Cabernet Sauvignon and Syrah.
You could easily make wine the theme of your whole holiday in Montemor.
Herdade do Menhir and Quinta da Plansel are seconds from the centre and are happy to show you their vineyards and wineries, offering a tasting at the end.
Monte da Ravasqueira is just up from Arraiolos and also has olive groves, so if you sit down to lunch here, many of the ingredients come directly from the countryside in front of you.
Food in Alentejo is as simple as it is delicious, relying only on ingredients from the region.
In the past a little had to go a long way, which is the spirit of açorda, a thick paste prepared using leftover bread, egg and olive oil.
Lamb and pork at the core of the traditional diet, and roasts and stews are flavoured with regional wild herbs like garlic, oregano, mint and coriander.
For a snack there’s empadas da galinha, small chicken pies, which are sold in bakeries.
And the dream accompaniment to the full-bodied local wine is Alentejo’s soft, creamy cheese, which like the wine has a designation of origin.