You're on a quiet stretch of ground above Linhó, an affluent village known for its gated resorts.
Last reviewed 29 October 2026 · A three-minute read · 1200–1980
The short answer
Avenida de Cascais sits in Linhó, Sintra, near the Hieronymite convent of Penha Longa founded in the 1300s and close to the former Colónia Penal de Sintra, an agricultural penal colony opened in 1912. The surrounding district still carries the colony's name, and the area now hosts resort estates and golf courses.
1958 to 1968
A wealthy village grew around an old convent
On the slope above you, about half a mile off, sits Linhó, Sintra, a wealthy village of gated estates and golf resorts. Its two best-known communities, Quinta da Penha Longa and Quinta da Beloura, grew up around a much older religious site. The Igreja da Penha Longa and its Hieronymite convent date back to the 1300s, though the church's current interior was built in the 1500s, under Cardinal-King Henry I.
Centuries later, Linhó became a staging ground for Portuguese politics. Marcelo Caetano, an ousted politician and university rector, bought a summer home there in 1958. He used it to host meetings and plan his return to power. A street in Linhó still carries his name, though some residents have pushed to change it.
1755
The great earthquake shook Sintra's hills
Three centuries before any of that, the ground under Sintra shook. On 1 November 1755, the great Lisbon earthquake tore through the region. It cracked the Pena monastery on the hills above the town and damaged buildings in Sintra itself, including the royal palace below, though the palace's Shield Room survived intact. Lisbon's own toll that day was catastrophic, and Sintra felt the same ground move.
That earthquake was not the region's first. Centuries of seismic records show Lisbon and its surroundings struck again and again: in 1151, with a thousand dead; in 1531, when an earthquake and the tsunami that followed it together killed an estimated 30,000 people and flattened 1,500 houses; in 1551, with 2,000 dead and 200 houses lost; and again in 1807, when 11 deaths were recorded. Sintra's hills stood over all of it.
1912 to 1960s
A penal colony gave the district its name
Half a mile from where you stand, down toward Sintra, a different kind of institution opened its gates. In 1912, under a law passed that July, Portugal created the Colónia Penal de Sintra. It took in vagrants between 16 and 60 and put them to work on the land, an agricultural penal colony meant to reform them through labor. The neighborhood that grew up around it still carries the name Bairro da Colónia Penal, Sintra, the district you're standing in now. The colony became the Estabelecimento Prisional de Sintra, a prison that still operates under that older name on the ground.
The Igreja da Penha Longa convent, the Hieronymite house mentioned above, is a National Monument.
1965 to 1966
A train crash and a wildfire struck Sintra
The twentieth century brought its own disasters to the municipality. On 20 December 1965, a train collision at Algueirão, within Sintra, killed 20 people. Less than a year later, wildfires burned across Sintra from 6 to 12 September 1966, killing 25. Both are recorded in Portugal's own disaster archives, and both happened within the same stretch of hills you can see from where you stand.
1980
A man was murdered in Sintra
In Sintra, in 1980, a man named Delfim de Almeida Fernandes was murdered. The record gives no more than his name, the year, and the town.
1999
A resort hosted a secretive global gathering
In 1999, the Ritz-Carlton Penha Longa Resort hosted a meeting of the Bilderberg Group, the private, invitation-only gathering of politicians and business leaders that draws global attention and secrecy in equal measure.
Afonso V of Portugal died in 1481 at Sintra. He had ruled Portugal since 1438 and was known in his lifetime as Afonso the African for his campaigns in Morocco.
1999 to now
Golf courses on the slope host championships
Back up the slope, the Ritz-Carlton Penha Longa Resort has kept hosting. Its golf courses, designed by Robert Trent Jones Jr., have carried the Open de Portugal three times. Quinta da Beloura, the other gated estate on the hillside, built its own course under the American architect Rocky Roquemore and now holds the Portuguese Golf Federation's annual national seniors' championship.
Giovanna of Savoy died in 2000, in Estoril, across the river from Lisbon. She had been queen consort of Bulgaria.
Luisa Isabel Álvarez de Toledo, 21st Duchess of Medina Sidonia, died in 2008, in Estoril. Luisa Isabel Álvarez de Toledo had held the Spanish ducal title of Medina Sidonia.
From this stretch of ground above Linhó, you can look toward a resort hillside that once sheltered a dictator-in-waiting and a prison colony that gave this district its name.
A Hieronymite religious house originally founded in the 14th century in Linhó, with the church's current interior rebuilt during the reign of Cardinal-King Henry I of Portugal in the 16th century.
The great earthquake of November 1, 1755 damaged the monastery at Pena and buildings across Sintra town, though the royal palace's famous Shield Room survived intact.
The Igreja da Penha Longa, a Hieronymite convent and church, stood on the slope from the 1300s, with its current interior rebuilt in the 1500s under Cardinal-King Henry I.
What happened at the Colónia Penal de Sintra?
Opened in 1912 under a law passed that July, it was an agricultural penal colony that took in vagrants aged 16 to 60 and put them to work on the land. It later became the Estabelecimento Prisional de Sintra, a prison still operating under that older name.
Did the 1755 Lisbon earthquake affect Sintra?
Yes, the earthquake of 1 November 1755 cracked the Pena monastery and damaged buildings in Sintra town, though the royal palace's Shield Room survived intact.
What disasters struck Sintra in the 1960s?
A train collision at Algueirão on 20 December 1965 killed 20 people, and a wildfire that burned across Sintra from 6 to 12 September 1966 killed 25.
What is the Bilderberg connection to this area?
In 1999 the Ritz-Carlton Penha Longa Resort, on the slope above Linhó, hosted a meeting of the Bilderberg Group, the private, invitation-only gathering of politicians and business leaders.
Why does a street in Linhó carry Marcelo Caetano's name?
Marcelo Caetano, an ousted politician and university rector, bought a summer home in Linhó in 1958 and used it to host meetings and plan his return to power, and a street there still bears his name.
Where this came from
1
Wikipedia — Igreja da Penha Longa convent and church
2
Wikidata — King Afonso V of Portugal died in Sintra