Pennywise Conquers the Navigli: The Milanese Event for the Launch of IT: Welcome to Derry

Pennywise Terrorizes Milan: The IT Event on the Navigli

by Elisa Giudici

27 October 2025 09:11

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A Saturday evening of ordinary terror on Milan's Navigli, and not because of the crowds or the price of spritzes, but due to the presence of a… terrifying guest. It is in this very crowded location that Sky and NOW chose to debut the latest trailer for IT: Welcome to Derry, the highly anticipated HBO Original and Sky Exclusive miniseries arriving from Monday, October 27 exclusively on Sky and streaming only on NOW, with a new episode every Monday in prime time on Sky Atlantic.

The appointment was set for seven o'clock sharp on Saturday, October 26, in front of the maxi-screen installed on the facade of a church under restoration, right next to the Alda Merini bridge. While waiting for the appointed hour, a small crowd gathered along the canal, awaiting the countdown to expire: at the seven chimes of the church bells, the official series trailer began on the screen, and immediately after, the entire stretch of the Naviglio, dotted with balloons and performers, turned red, with special lighting created for the event.

Pennywise Conquers the Navigli: The Milanese Event for the Launch of IT: Welcome to Derry

A Selfie with Pennywise

From the blood-red fog that enveloped the canal water, a gondola emerged: on board, none other than Pennywise, ready to greet the Milanese public in the most unsettling way possible, with laughter, monstrous props, and a few nods to the children present, who were more surprised than scared. Red balloons, flashing lights, and sinister laughter transformed the heart of the city into a scene from a serial nightmare, as the miniseries promises to do (you can already read the review in advance).

For visitors, there were plenty of opportunities for fun (and thrills) to take home a piece of Derry, the Kingian town closely linked to the character's genesis. There was a photobooth dedicated where you could take pictures hugging It, but a couple of fully made-up performers armed with balloons also circulated among the crowd, offering quick selfies to those who didn't want to face the long queue to have their encounter with Pennywise printed on photographic paper on the spot.

A Dive into 1950s Derry, a Stone's Throw from the Naviglio Grande

Everyone else could take home a different but equally themed souvenir: “Il Gazzettino del Naviglio”, a newspaper with curiosities and information about the series, as well as branded balloons and a live soundtrack with a band playing great American hits from the 1950s – the era in which the television prequel, directed by the director of the two films Andy Muschietti, is set.

To complete the atmosphere, a vintage car full of red balloons and numerous performers in vintage clothes – full skirts, coats, and cardigans – populated the streets, recreating the aesthetic of mid-century America, between a suspicious smile and a red balloon.

Set in the 1950s in the American suburbia so dear to Stephen King, IT: Welcome to Derry brings audiences back to the origins of the myth of Pennywise and the cursed city created by the king of terror in his 1986 novel. The series, developed for television by brothers Andy and Barbara Muschietti (who also directed IT and IT – Chapter Two) along with Jason Fuchs, explores the genesis of evil and the birth of collective fears that will forever mark the community of Derry from the perspective of some children attending the local school and that of an African-American family who have just moved to the city, with many connections to the Kingian universe and the rest of the story already seen in cinemas starring Pennywise.

The retro taste of the new production – from the music to the costumes – is inspired precisely by the American imagery of the Cold War era and the anti-communist paranoia of the 1950s, which Sky and NOW wanted to recreate with this event. The activities brought to the Navigli recall that world of country fairs, pastel diners, superficial smiles, and shadows hiding behind the apparent innocence of the American dream.

For the lucky ones present in the city to take advantage of the event and take home a souvenir photo with Pennywise, it was a magical moment. For everyone else, it's the perfect appetizer for Halloween week and for the arrival, overnight, of the new series that brings the IT universe back to life, while awaiting the dedicated events already announced for the Lucca Comics & Games weekend.

Pennywise Conquers the Navigli: The Milanese Event for the Launch of IT: Welcome to Derry

Pennywise Terrorizes Milan: The IT Event on the Navigli

A Selfie with Pennywise

A Dive into 1950s Derry, a Stone's Throw from the Naviglio Grande

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