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Fall Travel

America’s Coolest Fall Festivals

Music festivals. Harvest fairs. Pumpkin launching competitions... Read on for the best events coming to you this season.

Chelsea is Brooklyn-based travel writer, editor, and photographer. When not home eating her way through NYC, she's gallivanting across the globe, sailing the coast of Croatia or hiking the peaks of Peru. Her superpowers include booking flight deals and sleeping in small plane seats.

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Cider Week, NYC

There’s Oktoberfest for beer and Wine & Food Festival for vintages, and now, our favorite golden drink has a celebration of its own: Cider Week. Check out the cider and cheese fondue pairings at Murray’s Cheese Bar, seasonal tastings at Brooklyn Cider House, and hearty cuisine (including a signature pork and cider pie) at British-American gastropub Jones Wood Foundry. Details are still in the works, but last year's main event was Cider Fest, a free street fair on Orchard Street in the LES that featured autumn-inspired cotton candy, make-your-own caramel apples, and all the cider you could sip.

November 8-17, 2019

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Archtober, NYC

In October, New York City opens the doors to its most historic, exclusive buildings for Archtober, a month-long architecture and design festival. The calendar is stocked full of site tours, talks, film screenings, architecture boat trips, and exhibits at the Smithsonian Design Museum, Museum of Modern Art, New York School of Interior Design, and The Guggenheim, to name a few. We love the Building of the Day tours, where architects walk you through notable structures like the Stephen A. Schwarzman Building (also known as the venerable New York Public Library), the newly redesigned Eleven Madison Park restaurant, and the Tenement Museum.

October 1-31, 2019

RELATED: 7 Under-the-Radar Things to Do in NYC

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Photos courtesy of Maclay Heriot and Cambria Harkey


Austin City Limits, TX

Austin has been called the live music capital of the world, and it’s not hard to see why at the annual Austin City Limits festival. Expect two jam-packed weekends of more than 110 musicians, some of the city’s best bites (ahem, tacos), Barton Springs Beer Hall, and an eclectic art market of local crafts and wares, all set up in the 350-acre Zilker Park. This year the lineup includes Guns N' Roses, Mumford & Sons, The Cure, Cardi B, Billie Eilish, and more.

October 4-6 and 11-13, 2019

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Photo by Jennifer Mitchell


Blaze, Croton-on-Hudson, NY

Hudson Valley is not a newcomer to Halloween festivities (just ask Sleepy Hollow). But while it’s worth a day trip just to see the spooky decorations, go at night for The Great Jack O'Lantern Blaze, where the 18th-century Van Cortlandt Manor and its sprawling grounds are covered in more than 7,000 hand-carved jack o’lanterns. Remember to bring your camera for the perfect pumpkin pic.

September-November 2019

RELATED: How to Plan a Romantic Weekend Away in the Hudson Valley

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Photo by Ed Smith


Oktoberfest by the Bay, San Francisco

The same city that brought us Bay to Breakers and Outside Lands also happens to host one of the country’s biggest parties, Oktoberfest by the Bay. Pier 35 transforms into a massive German-style extravaganza, where crowds come for traditional Bavarian dancing, live music, and ice-cold Spaten lager. Two weekends after that, look out for more pretzels and partying in Oakland, where the craft beer-centric Oaktoberfest (October 5-6) takes over the city’s 40-some local breweries.

September 20-22, 2019

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Photo courtesy of Sonoma county Harvest Fair


Sonoma County Harvest Fair, Santa Rosa, CA

September and October marks wine season, called crush, which is the centerpoint of Sonoma’s Harvest Fair. While you could easily spend the whole weekend sampling award-winning wines, craft beer, and farm-to-table fare, leave time for the epic grape stomp competition.

October 4-5, 2019

RELATED: The 7 BEST Hotels in Sonoma Valley

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Photo by John Valls


Feast Portland, Portland, OR

Now in its eighth year, Feast Portland remains one of the most talked-about events in the Pacific Northwest. Celeb chefs come from all around the country to host cooking classes, collaborative dinners, food, wine and craft beer tastings, “Drink Tank” panels, and a massive night market. We’re already drooling over the epic smoke-out (pictured above) where grill-meisters sling Flintstonian cuts of meat.

September 12-15, 2019

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Photos courtesy of Lyssa Ann Portraits


Country Living Fair, Atlanta, GA

Shoppers unite! Country Living magazine is welcoming 250+ vendors to come sell vintage wares and antiques at its roving flea market. Besides the craft and culinary demonstrations, you’ll also have the chance to meet the editors as well as pick up tips and tricks from famous TV stars like Erin and Ben Napier of HGTV's Home Town and Nancy Fuller of Food Network's Farmhouse Rules. Bonus: The southern-style food is to die for—try juicy BBQ, pumpkin rolls and freshly squeezed lemonade.

October 25-27, 2019

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Photo by Noah Fecks


Food Film Festival, NYC

So long, soda and stale popcorn. At the Food Film Festival, you’ll be served the same food you see on screen. The four-day fest kicks off with opening night, dubbed Deep Flavor Dive, which will feature "intense films, foods, and flavors" around the world including Arctic Greens (how one couple in Greenland grow lettuce in the ice and snow) and What's Eating Dan? Garlic Bread. (get ready for some need-to-know cooking tips). Truth be told, we're most excited for The Sturgeon Queens on the 27th, which recounts the tale of four generations of a Jewish immigrant family  who started now-iconic LES restaurant Russ & Daughters. It’ll be a feast for the eyes—and the stomach.

October 24-27, 2019

fresh orange pumpkins on a farm field.

Punkin Chunkin, Bridgeville, DE

What do you get when you combine pumpkins and catapults? Punkin Chunkin, Delaware’s wacky (and slightly redneck) fall fest. Imagine tricked-out trucks launching gourds into the sky from manmade trebuchets and cannons. Think of it as a physics science experiment turned hilarious engineering competition. For those more interested in eating their pumpkins than tossing them, check out the Punkin Cookin Contest or the chili cook-off. You may even be crowned queen of the Punkin Chunkin Pageant.

November 1-3, 2019

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