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Discover quintessential fall with these can't-miss festivals

Crisp, cool air and colorful leaves make fall the perfect time to amble through outdoor festivals in beautiful international cities. | By Laura Burkehart | September 1, 2022 (Updated October 3, 2023)

Celebrate the changing seasons with fall festivals in international cities famed for autumn color, iconic scenery and unique flavors. Follow along and discover cultural events worthy of world-class destinations in Chicago, New York and Berlin.

  • Heighten your senses: Food, film and music festivals fill the Windy City fall lineup

  • Cocktails, comedy and culture: Enjoy walk-around tastings, comedy shows or panel discussions for a well-rounded New York getaway

  • Raise a glass: Pack your lederhosen for the ultimate Oktoberfest experience

Chicago skyline in Autumn
See the leaves fall on the lakeshore in the Windy City.


The finest of everything the Windy City has to offer is abundant in autumn. Food, film and music are all in the lineup of fall activities, so prepare to heighten your senses and revel in some of the most renowned festivals and cultural events.

Enjoy everything from street food to sommelier sessions during Chicago Gourmet. The four-day festival kicks off with Tacos & Tequila, hosted by acclaimed chef Rick Bayless on the rooftop of the Harris Theater. Overlook Millenium Park while tasting tequila and mezcal paired with delicious Mexican cuisine prepared by top culinary artists from Chicago and Miami. Other noteworthy events include competitive sommelier sessions and Prost! In the Park, celebrating Oktoberfest stateside. Your personal concierge at Waldorf Astoria Chicago can help with planning and transportation so you don’t miss a thing.

The stars align in October at North America’s longest running competitive film festival. See the work of past and future Oscar winners at the Chicago International Film Festival. Acclaimed international directors present feature-length and short films touching on diverse topics. Cinephiles can spend blissful hours viewing documentaries, comedies, dramas and even horror movies artfully presented in person and virtually.

Swing by the Chicago Cultural Center by Millennium Park — it’s the hub for the World Music Festival, though shows take place in venues around the city. Musicians from nearly two dozen countries perform during this weeklong celebration of peace and sound. The finale takes place at Navy Pier, which is a pleasant (and convenient!) 1.5 mile (2.5 kilometer) walk from Waldorf Astoria Chicago.

Person in pink runs through park with autumn leaves
Whether you're staying uptown or downtown, fall is a great time to be in the Big Apple.

New York

America’s cultural mecca, New York, has a diverse schedule of exciting festivals each fall. Stimulate your palate and mind at events with top-tier personalities and offerings. Get inspired by the fine art within Conrad New York Downtown before heading out on the town. All about location? Conrad New York Midtown, in the heart of Manhattan, makes a perfect home base for cultural outings given its proximity to some of the city’s top museums.

Gastronomes will delight in exploring the finest flavors at the New York City Wine & Food Festival. Sample hundreds of wines, spirits, culinary experiences — and of course, fantastic food — in locations across the city. Participate in walk-around tastings and attend master classes to learn the best methods for making chocolate, cocktails and more. Celebrity chefs and other notable names will be on hand to sign cookbooks and host events. If your appetite isn’t quite sated, head to Dabble at Conrad New York Midtown where you can sip on a restorative blood orange and ginger cooler while sampling light bites.

Big names bring big laughs at the annual New York Comedy Festival. Produced by legendary comedy club Caroline’s on Broadway since 2004, this event runs for ten days. Prepare for belly laughs — around 200 A-list comedians and up-and-comers will perform, telling jokes and stories at more than 100 shows around the city’s five boroughs. Check out all-access panels with the cast, writers and producers from popular television programs as well as sketch comedy shows and competitions.

Anyone with an intellectual bent will enjoy The New Yorker Festival. Celebrate every aspect of culture over this October weekend. Events include cocktail parties, panel discussions, screenings and concerts with entertainers, authors, scientists, chefs and more. Contact your concierge for help planning so you make it to the sessions you’re most excited about.

Man sitting on the couch and looking at the view of the city
Fall in Berlin makes for a breathtaking sight.


Stroll through Berlin to see spectacular fall colors amid both modern architectural gems and historically significant structures. Climb the 285 steps at the picturesque Victory Column for sweeping views over the Tiergarten and Bellevue Palace. It’s a brisk walk from there to Waldorf Astoria Berlin, which boasts its own spectacular vistas. Located on the 15th floor, The Library lounge is the perfect location for high tea in a relaxed atmosphere overlooking the city before visiting at the hotel’s award-winning Guerlain Spa for a relaxing treatment or moment of calm in the sauna and steam room.

For 10 days in October, Berliners’ nights are bright as buildings and landmarks are illuminated during the Festival of Lights. Each year, a new motto for the event is revealed — this year’s is “Colours of Life” — and the works of light art are designed around related themes. Multiple installations on Bebelplatz, a public square, are accompanied by music. Potsdamer Platz is also considered a hotspot for colorful projections.

If there’s one festival that’s synonymous with autumn in Germany, it’s Oktoberfest. This epic celebration goes on for six weeks throughout September and October, as Berlin is overtaken by all things Bavarian. Festivities take place across the city in neighborhoods, at restaurants and pavilions and under enormous party tents. Revelers can get their fill of sausages, strudel, pretzels and beer. The party also comprises carnival rides, performances, Bavarian music, folk dancing and traditional dress. Don your lederhosen or dirndl and join the fun — Oktoberfest is truly found on every corner in autumn.

This fall, whether you are looking for an authentic cultural experience in a beer hall in Berlin, an amusing respite with comedians in New York or gourmet samplings with the finest chefs in Chicago, you’re sure to find a festival that piques your interest in these sophisticated international destinations.

Laura Burkehart is an editor and writer who loves travel as much as she loves writing about it. She splits her time between North Carolina and Northern California.

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