Best Things to do in Milan in the Fall

By Andrew Thompson

Milan is an amazing year-round destination. Although the northern Italian city sees most of its tourist traffic during the summer months, those in the know say that fall is the best time to visit Milan. That’s because fall in Milan is quieter and cooler than during peak summer, and yet there are still dozens of things to do in Milan at night, and plenty of seasonal activities to keep you busy during the day. Many of the best things to do in Milan this fall take the form of annual events, sporting matches and festivals, and the seasonal foods and changing seasons make it a fascinating time to visit. Milan is also one of the world fashion and design capitals, offering up a perfect balance for everyone. So if you’re wondering what to do in Milan this fall, one of these things should keep you busy as you explore the beautiful iconic city.

Explore the autumnal leaves in the parks

Milan’s parks are beautiful regardless of the time of year, but a casual walk or cycle through them during September, October or November is one of the best things to do in Milan this fall. That’s because the leaves in most of the parks start to change color, making for a true spectacle, and the cool autumn air is perfect for some outdoor activities. Most neighbourhoods have small parks to explore, but Parco Sempione, close to Castello Sforzesco, is always a superb option. Alternatively, Giardini Pubblici Indro Montanelli is worthy of a visit all on its own, particularly if you are visiting Milan in October or November.

Watch a soccer spectacle

Soccer is a national obsession in Italy, and there are few better places in the world to take in a match than at the city’s San Siro stadium. If you’re wondering what to do in Milan this fall that gives you some insight into local culture, then this might be it. The games here are full of life, and there’s no better way to immerse yourself in the city than by picking a side and screaming your lungs out for them. There are games at the stadium throughout the soccer season, and tickets for the big matches sell out in advance, so do some careful planning and research if this is high on your list - but you don’t need me to tell you that.

Experience Milan Fashion Week

Milan is an international fashion capital, and if your trip falls in the first weeks of September 2019 you’ll undoubtedly be caught up in the biggest fashion spectacle of the year - Milan Fashion Week. In 2019 it starts on the 17th of September and runs through until the 23rd. Although the actual shows are often off-limits to tourists or sell out months in advance, the festival still radiates energy throughout the city. Models, designers and celebrities strut the streets in the lead-up and aftermath, and if you’re a fan of the fashion scene and wondering what to do in Milan in September, hanging out at the city’s bars, restaurants and public places over this time may just be the highlight of your trip.

Take in an opera performance at La Scala

If the weather in Milan starts to turn a little cooler than you’d like, and you’re looking for one of the best cultural things to do in Milan at night, book some tickets to a night at the opera. If you’re visiting Milan in November, you’ll be pleased to know that this is also the start of opera season in the city - and there are regular performances that will leave you speechless and only wanting more. If opera isn’t exactly your favourite way to spend an evening, but you still love to explore the cultural side of a city, there are noteworthy performances at La Scala throughout the year - including performances from famous singers and a range of ballets and theatrical performances.

Celebrate halloween

Halloween may not be a traditional Italian holiday, but as in many other places around the world it’s taken off in recent years and is a fun day to experience in the city. There’s something quite unique about celebrating the 31st of October in a place like Milan - many restaurants, bars and nightclubs get in on the action, starting on All Saint’s Day, and it’s hard not to get caught up in the atmosphere. If you take your Halloween celebrations seriously, there’s a good chance you’ll also find a dress-up party at one of the city’s nightclubs, so either pack accordingly, or kit yourself out by visiting one of the city’s many stores.

Run the city

If you’re a fan of using running as a way to experience a new city, then plan your trip around the annual Deejay Ten event. It’s an annual fun run that takes place in the heart of Milan during the fall, and the emphasis is on enjoyment rather than competition. There are five and ten-kilometre options, making it a great way to get involved in the city if you’re not afraid of a bit of exercise. There’s also a popular celebration at the finish line, and the energy from the runners spreads out throughout the city on the event day. In 2019 the run takes place on the 13th of October. 

Milan Jazz Festival

The Milan Jazz Festival is another annual event that takes place in November. The city has several celebrated jazz clubs, and over the course of the annual festival these play host to some of Europe’s best shows. Each year there are some 500 artists who attend the two-week festival, ranging from up and coming musicians to national and global superstars. They play at 150 different events dotted throughout the city, and it’s a remarkable time to visit and soak up some of the musical culture of Madrid.

Visit the EICMA Motorcycle Show

Italy is no stranger to fast cars and motorcycles, and if you’re looking to experience the best of the latter then plan your trip around the EICMA Motorcycle Show. It’s a motorcycle expo attended by enthusiasts from around the world, and during the course of the four day annual festival you’ll get to witness some of the best two-wheel machines in the world. It’s a motorcycle sensory overload that’s the perfect match for a cool autumn afternoon. The festival runs between the 7th and 10th of November, and tickets often sell out weeks in advance.

Watch the Milanoltre Dance Festival

For the last 30 years, the Milanoltre Dance Festival has attracted fans of dance from around the world. This annual festival runs from September to October each year, and features a range of theatrical and dance-related events that continue to wow audiences. The festival has found a good mix between established, well-known performers, and young, up-and-coming dancers. It also caters to a variety of tastes, with the main showcase falling on contemporary dance, and it’s an unmissable annual event if you’re a fan of dance or captivating live performance.

Day trip to Como

Although there’s more than enough to keep you busy throughout the months of fall, there are also several noteworthy day trips from Milan, Italy to include in your schedule. During the fall, the best of these may just be a day trip to famous Lake Como. The beautiful, lavish lakeside town of Como offers delights throughout the year, but come autumn many of the trees surrounding the pristine waters change color and offer the ultimate autumnal show. It’s a superb time to visit the famous lake, and although many choose to stay over, it’s also very doable as a day trip from Milan.

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