IRONMAN Portugal 2019
João Filipe | IRONMAN Portugal 2019
João Filipe

The best things to do in Cascais in October

Despite the grey days on the way, there’s an IronMan to test your limits and plenty of cultural events to enjoy in Cascais this October.

Hugo Geada
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Cascais becomes a cultural and sporting hub in October, with a varied programme offering something for everyone. In sport, the highlight is the return of IronMan, one of the world’s most demanding sporting events. But there are also more relaxed options on the music and food calendar, including the mouth-watering ULU x KAU collaboration, the opera La Vera Costanza, EVOLUTION Bar Fest and an ABBA tribute. There’s also an opportunity to help the community with the ComDignitatis charity show, while fashion and debate share the spotlight at Fall Market Stylista and Conferências do Estoril. Despite the rain and grey days settling in, the motto remains the same: there’s no standing still in town.

Recommended: What's new in Cascais

October in Cascais

  • Film

In October, Fundação Luís I’s film season brings the best in horror cinema to the auditorium at Centro Cultural de Cascais. With free screenings on Mondays at 6pm and 9pm, the programme brings together four landmark films that shaped the genre: the classic Frankenstein (5 Oct), the masterpiece Psycho (12 Oct), the disturbing Peeping Tom (19 Oct) and the essential Night of the Living Dead (19 Oct).

  • Things to do
  • Talks and lectures

Nova School of Business and Economics (Nova SBE), in Carcavelos, hosts the tenth edition of Conferências do Estoril on 29 and 30 October, under the theme ‘Reignite Democracy’. Held as part of Cascais’s year as European Capital of Democracy 2026, the international forum aims to debate the main global challenges, with a particular focus on polarisation, disinformation and strengthening democratic institutions. The event will bring together world leaders, academics, businesspeople, Nobel Prize laureates and young leaders.

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  • Art

Quinta do Pisão, in Cascais, hosts the 12th edition of LandArt Cascais until 1 November 2026. Curated by Luísa Soares de Oliveira, the biennial exhibition promotes a symbiosis between contemporary art and nature, presenting two striking installations: Pedro Cabrita Reis’s geometric and minimalist sculpture A Probable Horizon #8, which redraws the horizon across the open field; and Susanne S. D. Themlitz’s enigmatic and surreal intervention The Listener, set in an old water tank.

  • Things to do
  • Late openings

Quinta do Pisão hosts a themed night walk dedicated to discovering and observing the bats and flying mammals that inhabit the nature reserve. The initiative aims to introduce participants to the different local species, dispel myths and highlight the vital ecological role these animals play in preserving biodiversity and maintaining the balance of terrestrial ecosystems.

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  • Art

Cristóbal Toral spent his childhood working the land with his father, a charcoal burner, in Antequera, Andalusia. A group of local hunters happened to discover the drawings he made in his spare time – an episode that changed his life and led him to study art. Today, he is considered a leading name in contemporary Spanish realism – and his work can be seen at Centro Cultural de Cascais until 17 January 2027. Curated by the artist’s wife, Marisa Oropesa, the exhibition Cartografia do Tempo – Uma Eterna Viagem – the first in Portugal dedicated to Toral’s work – brings together 44 works, mainly paintings and sculptures.

  • Music
  • Music venues

The main aim of this charity concert is to raise funds for the construction of Casa das Janelas Grandes, in Mafra, the charity’s new building dedicated to urgent support in children’s and young people’s mental health, autism support, home care and a day centre. Hosted by José Carlos Malato, the charity gala will bring together a varied line-up of Portuguese artists: Anjos, Brisa, Carlos Machado Vidal, Inês Fonseca, the cast of the musical O Feiticeiro de Oz, Nuno & Henrique Feist and Rita Guerra.

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  • Art

The Exemplary Girls was written by the Countess of Ségur in 1858. The children's book by the Russian author—who wrote this and many other adventures about well-born girls who behave terribly—now lends its name to the new exhibition at Casa das Histórias Paula Rego. Curated by Catarina Alfaro, it features the female figure, both in childhood and adulthood, as the protagonist and presents, for instance, the hand-coloured lithographs The Salmon-Coloured Dress and Communion, inspired by poems by Adília Lopes. The exhibition, which is open until the end of January 2027, also includes works from the "Jane Eyre" (2001-2002) and "Pendle Witches" (1996) series, influenced respectively by the work of Charlotte Brontë and Blake Morrison, as well as the six prints of "Female Genital Mutilation", a 2009 series that denounces practices of gender-based violence affecting girls in various parts of the world.

  • Art

Coinciding with As Meninas Exemplares, Casa das Histórias Paula Rego’s long-term exhibition O Exilado: da criação à conservação is dedicated to the technical study and restoration of a work – a process that usually takes place far from visitors’ eyes. The work in question is the painting-collage O Exilado (Um velho exilado sonhando a sua juventude), from 1962-63, shown for the first time in Portugal and accompanied by images and behind-the-scenes explanations of the research and conservation process. The study revealed hidden collages, compositional changes and layers of materials that help shed new light on the Portuguese artist’s creative process.

More Cascais

  • Things to do

Few capitals in the world can boast this particular perk: paradise-worthy beaches less than an hour away. The Cascais coast, for example, just 40 minutes by train from Cais do Sodré, brings together some of the busiest and most versatile beaches in the region. You can get there along the Marginal, of course, or even by motorway, but the train journey – with the river first and the sea later in full view – is well worth it. To help you plan your next day in the sun, Time Out hit the coast and picked 13 essential stops, from urban beaches with calm waters to retreats made for wave sports. From Carcavelos to Guincho, we map out where to lay down your towel. Just remember: there are no miracles. In July and August, parking and access roads get seriously busy, so public transport really is the most efficient way to avoid the queues. Choose your next destination and make the most of summer.

  • Things to do

Making the most of Cascais does not have to leave your wallet in ruins. Between the deep blue of the Atlantic and the dense greenery of the natural park, the town hides a generous share of heritage, culture and leisure that is entirely free to enjoy. Whether you want to lay down your towel on beaches sheltered or wild, lose yourself on trails and dunes along the rugged coast, walk among peacocks in historic gardens or dive into the town’s strong arts scene in the Museum Quarter, there are plans here for every taste and age. So you can enjoy the region without spending a single euro, Time Out has put together the essential guide to the best free things to do in Cascais.

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As tempting as the beaches and Atlantic waves may be – and as good as a plate of fresh fish at one of the region’s best restaurants always sounds – Cascais is far more than a seaside escape. Come sundown, the town has plenty of bars that invite you to slow down and stay a while, whether you are into wine, craft beer or cocktails. From rooftops with a view, such as Blue Bar, to the industrial curiosity of Ukrainian brewery Pravda; from the natural wines at Holy Wine to the match-day spirit of Crow’s Bar, there is something here for every mood. Palaphita, at Casa da Guia, and Bar do Guincho, overlooking the Abano dunes and the Sintra hills, keep things close to nature, while Cascais Jazz Club holds on to the town’s classic bohemian charm. These are the best bars in Cascais that Time Out has tried, tested and recommends.

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