Concerts, exhibitions, markets, wine, and outdoor sports: from October 23 to 25, Milan is brimming with events for every taste. Here are 15 ideas to mark on your calendar for the weekend, both in the city center and the surrounding areas.
A Final Toast to Milan Wine Week
Milan Wine Week is drawing to a close, but there are still several events at Dazio di Levante where you can raise a glass. On Friday, October 23, starting at 6:30 p.m., there’s the White Oak Winery Night, with free admission from 8:00 p.m. On Saturday, an evening dedicated to Tellus wines is on the schedule, while on Sunday, starting at 6:30 p.m., the Closing Party officially wraps up the event. At the Enoteca, you can also sample wines by the glass, with prices ranging from €5 to €15.
Join the jury of The Jury Experience: Mortal AI
A vehicle is involved in a fatal accident: who is responsible? In this interactive show, the audience becomes the jury, listens to testimonies, evaluates the evidence, and votes on the verdict. The experience lasts about an hour; tickets start at €25.
JAZZMI Brings Music Throughout the City
The JAZZMI festival brings Milan’s clubs and cultural venues to life with concerts and events dedicated to jazz. Among the events scheduled for the weekend: Songhoy Blues at BIKO on Friday night, Amii Stewart at the Blue Note on Friday and Saturday, and CORTO.ALTO at Santeria Toscana 31 on Saturday.
Friday also marks the opening of the photography exhibition *Il tempo del jazz* at Volvo Studio Milano: admission is free, and the exhibition runs through November 7.
Two Days of Vegan Cuisine and Culture with MiVeg
MiVeg is back—the festival dedicated to animals and vegan culture. The program includes booths, talks, workshops, exhibitions, and plant-based culinary offerings; admission is free, with the option to reserve a ticket and make a voluntary donation.
Matisse at MUDEC: Art and Distant Cultures
For an indoor option, MUDEC is hosting “Matisse: The World in a Room”—about 100 works that chronicle the artist’s encounters with the cultures that helped shape his artistic language. The exhibition runs through February 21, 2027.
Try winter sports in the city with the Milano Mountain Show
For an outdoor weekend, the Milano Mountain Show Village brings the mountains to the city. In Piazza Città di Lombardia, you can discover various outdoor sports and try activities related to downhill skiing, cross-country skiing, biathlon, and cycling. Registration is free.
From Marching Bands to Miles Davis
On Saturday afternoon, Milanese marching bands will parade through the city center as part of “Bande in Festival”: the parade departs from Piazza Duomo at 3:45 p.m. and arrives at the Conservatory, with free admission. On Sunday, the Conservatory celebrates the centennial of Miles Davis with a free conference (reservation required) from 10:30 a.m. to 5:00 p.m., an exhibition at 7:00 p.m., and the “Sketches of Miles” concert at 8:00 p.m.
Enter the Duomo Archives with Archivi Aperti
For “Archivi Aperti,” the Veneranda Fabbrica del Duomo is offering two free guided tours of its photo archive and the images that tell the story of the Cathedral. Each tour lasts one hour; reservations are required by emailing archivio@duomomilano.it.
Hunt for rare records at the Novegro Vinyl Expo
Featuring vinyl records, CDs, memorabilia, and musical rarities, the Novegro Vinile Expo brings together over 150 exhibitors. There will also be meet-and-greets and book signings with artists, including Mauro Pagani. Online tickets cost €8 for one day and €12 for both days; tickets can also be purchased at the box office.
Stroll Among Antiques and Vintage Finds Along the Naviglio
On the last Sunday of the month, the Mercatone dell’Antiquariato returns, with hundreds of vendors lining nearly two kilometers of the canal. In addition to antiques, you’ll also find vintage clothing and items—a great way to browse the stalls and continue your stroll along the Navigli.
Choose your concert from pop and punk rock
On Saturday night, there are several options for live music. Alfa is set to perform at the Unipol Forum, while Ligabue wraps up his 2026 tour at the Unipol Dome. Meanwhile, Simple Plan is coming to Alcatraz: doors open at 6:00 p.m., and the band is scheduled to take the stage at 8:50 p.m.
Watch “Gloria – The Musical” at the TAM
At the Teatro degli Arcimboldi, “Gloria – The Musical” makes its debut—the story of a young artist pursuing success amid love, friendship, and family conflicts. The show features music by Umberto Tozzi and runs through November 1.
Back to the theater with *L’orologio americano*
Arthur Miller’s *The American Clock*, directed by Elio De Capitani, comes to the Teatro Elfo Puccini. The play tells the story of a community overwhelmed by the Great Depression and presents an ensemble-driven portrait that blends theater and cabaret. On Friday, October 23, there will be a preview for those under 30 at 7:30 p.m., with tickets priced at €6; the show is also on the program for the weekend.
Dance Tells the Story of “Il danno”
Choreographer Susanna Beltrami brings *Il danno* to the stage, a dance performance inspired by Josephine Hart’s novel. Desire, guilt, and memory take shape through the dancers’ bodies and imagery in a performance lasting approximately 70 minutes. Tickets start at 20 euros, excluding advance-sale fees.
Two Exhibitions at Palazzo Reale: Picabia and Youth and Future
At Palazzo Reale, you can visit “Picabia: Opening the Doors of the Night,” a retrospective dedicated to the French artist, open through January 24, 2027. In the Sala delle Cariatidi, you can also visit “Youth and Future,” a project dedicated to the younger generations, running through November 1: an event you won’t want to put off too long.
Between a concert, an exhibition, and a stroll among the market stalls, the weekend offers plenty of opportunities to switch things up every day.
Now all that’s left is to pick your favorite events, plan your schedule, and let yourself be surprised by everything happening in the city from October 23 to 25.
