The best things to do in Cascais in October

There’s no race quite like this. Whether you take part or just watch the athletes, it’s 3.8 kilometres of swimming, 180 kilometres of cycling, and a full marathon of 42.2 kilometres. All of this takes place with thousands of participants travelling from around the world to swim, cycle, and run against the stunning natural and architectural backdrop of Cascais.

Spring, Summer, Autumn, Winter: there’s no season Maria Guedes misses. Four times a year, you can find her (and her favourite brands in fashion, décor, and lifestyle – over 100, almost all Portuguese) at FIARTIL. Lively atmosphere, food, and drinks are never in short supply. The next edition takes place on October 4 and 5.

The world of classic cars returns to the Estoril Circuit for another edition of the Estoril Classics. From October 3 to 5, there will be demonstrations, parades, and races featuring Formula 1 single-seaters, sports cars, and touring cars. This edition is particularly special as it coincides with the 75th anniversary of Formula 1, motorsport’s premier category. Various tickets (some even including paddock access!) and the full programme are available online.

As the month draws to a close, it’s time to celebrate Halloween and the world of witches and ghosts. This year, Quinta do Pisão, in the Sintra-Cascais Natural Park – a beautiful setting that can also feel a little eerie – hosts a Halloween Dinner where pumpkin takes centre stage. There will also be a quiz, and the event is designed for families, welcoming children from six years old. Kids up to 10 attend for free, those aged 10 to 13 pay €20, and from 14 upwards it’s €35. Bookings must be made online.

Organised by the Fundação D. Luís I with the support of the municipality, this exhibition presents an unprecedented selection from the Américo Marques Contemporary Art Collection, bringing together around thirty works by more than 20 Portuguese artists or those closely connected to the country. Featured names include Julião Sarmento, Lourdes Castro, Pedro Cabrita Reis, Maria Helena Vieira da Silva, João Louro, Susana Mendes Silva, Pedro Calapez, Michael Biberstein, Ângelo de Sousa, and Fernando Calhau. Curated by Sérgio Fazenda Rodrigues, A Deslocação do Olhar highlights clusters of painting and video to encourage reflection on the gaze and its relationship with the image.

Indie, not a bookshop is much more than a bookstore specialising in signed editions and English-language titles: it offers a packed programme ranging from silent parties to writing retreats. Until the end of the year, once a month, you can join a book embroidery workshop with artist and teacher Mafalda Castela, who will show how to personalise books by stitching designs onto their covers. Participants, who must register in advance and pay €20, can bring their own books or use the covers provided by the shop. The workshops take place at Indie’s “older sister,” Déjà Lu – the second-hand bookshop right next door.

D. Maria Pia de Sabóia’s birthday is being celebrated with a dinner organised by Cascais FoodLab, featuring a very special guest: gastronome and researcher Vírgilio Nogueiro Gomes, who recently published the Novo Dicionário da Cozinha Portuguesa. This experience at the stunning Casa de Santa Maria includes an exclusive look at part of the queen’s menu collection – written in French and always featuring roast, punch, and sweet rice – which were donated to the Cascais Municipality by Vírgilio Nogueiro Gomes.

The Rally of Lisbon will once again have a major presence in Cascais in 2025. From October 30 to November 1, there will be timed stages in Alcabideche and Peninha, in the neighbouring municipality of Sintra, with the grand finale taking place at Cascais Marina – where a City Stage will be held, followed by the awards ceremony celebrating the drivers.

Fancy a seaside run? No need to get your feet wet. The Lisbon Marathon takes place on October 25, with a new start at 8.00 in Carcavelos, right outside Nova SBE. The 42-kilometre course offers views of the sea and the river all the way to the finish line at Praça do Comércio.

To mark the 150th anniversary of Carmen’s premiere, the Estoril Flamenco Festival presents a bold interpretation of this classic at the Casino, performed by the Barcelona Flamenco Ballet. The original story is brought into the 21st century through the power and expressiveness of flamenco. The performance takes place on 24 October, with tickets priced between €30 and €45.

Directed by Paulo Sousa Costa, the iconic play Le Dîner de Cons (Dinner for Idiots) returns to the stage in Cascais from 16 to 18 October. It will be performed at the Estoril Arts Academy, housed in the Edifício Cruzeiro, with a cast that includes Ângelo Rodrigues, Rui Porto Nunes, Liliana Santos, Núria Madruga, and João Didelet, among others.

A trip to Ireland without leaving Cascais. On 3 October, the Casino Estoril welcomes Celtic Legends – The Life in Green in the Salão Preto e Prata. The show immerses audiences in the spirit of Irish culture, from traditional music and dance to the lively atmosphere of a pub. Tickets are priced between €25 and €45.