The Best Places to Travel in October

Sep 26, 2019

From traditional Bavarian oompah bands in southern Africa to experimental music in the palazzi of Venice, October's sounding like a whole lot of fun. The month is looking pretty dazzling, too, with psychedelic foliage, horseback eagles and everything in between. So pack your dirndl and dancing shoes, and hit the road.


A full century has passed since this country was a German colony, but—what with old habits dying hard—Oktoberfest Namibia (Oct. 25 – 26) remains a full-fledged lederhosen and brau bash right here at the doorstep to the Namib Desert, a party worth joining for the improbability factor alone. One of Oktoberfest Munich's traditional bands plays Windhoek for the occasion, so grab a glass of locally-brewed Festbier and start slapping those leather-bound knees in your best approximation of a Schuplattler dance. There’ll be tons of Bavarian eats—think brezen (pretzels), würstl (sausages) and schweinebraten (roast pork). And though you may work some of it off at fairground games that range from log-sawing to beermug-hoisting, you'd do even better to hike up and run down some of the planet's tallest (and most devastatingly beautiful ) dunes. Don't leave without checking out the abundant local wildlife: October happens to be a great time to safari through Etosha, Namib-Naukluft and Skeleton Coast National Parks.

Upstate New York

Feast your eyes on October’s psychedelic fall foliage, then indulge your palate at the Saratoga Food and Wine Festival (Oct. 4 – 5). The event kicks off with a Farm-To-Table Harvest Dinner by the Spa State Park reflecting pool, complete with live music, wine—and canapés courtesy of  chef Tim Spedding (formerly of the Michelin-starred Clove Club in London). Antique hunters will want to stick around for the nearby Warrensburg Garage Sale (Oct. 5 – 6), reportedly the largest garage sale on earth. After checking out the goods of some 500 street vendors, refuel with a well-earned 18-inch roast beef sub at the legendary Jacobs & Toney Deli.


The local Art Biennale may hog the limelight, but Venice Music Biennale (Sept. 27 – Oct. 6) is an experimental music fest that’s well worth the jaunt. In a stunning lineup of centuries-old venues, you'll hear everything from human-robotic fusion to a blend of 17th-century chamber music and electronica. To round out your listening tour with something more traditional, book tickets to The Barber of Seville and/or Madame Butterfly, both at the iconic Gran Teatro La Fenice during the first week of the month. (Stay through Oct. 24 and you can also catch La Traviata.) A short walk away, at the newly-opened Experimental Cocktail Club, toast to your time here with an impeccable Bellini.


The Michelin stars will be twinkling over Oahu at  Hawaii Food & Wine Fest (Oct 5 – 27). Though you'll eat absurdly well for the duration, the grand finale is the event to catch: The Halekulani Culinary Masters Gala Dinner (Oct. 27) features six Michelin-starred chefs who've come from as far as Tokyo (and as near as Honolulu). If wine is more your thing, don't miss Swirl (Oct. 25) a rooftop party overseen by master sommelier, Christopher Ramelb. And if last night’s vintage reds start to catch up with you, chill by the infinity pool of the brand-new Halepuna Waikiki


Give yourself the red carpet treatment, and snag some tickets to this year’s Chicago International Film Festival (Oct. 16—27). There’s an exciting roster, including Martin Scorsese’s The Irishman and Gael García Bernal’s Chicuarotes. Keep the culture theme going at Open House Chicago (Oct. 19 – 20), when you can get VIP access to more than 350 iconic buildings, not least Frank Lloyd Wright’s Oak Park masterpiece: Unity Temple. (For the total building binge, tack on an architectural river cruise.) Then recharge with an espresso martini at Lazy Bird: a speakeasy-style cocktail bar in the basement of the newly-opened Hoxton Chicago.


If you thought the documentary version of The Eagle Huntress was riveting, check out the live-action version Oct. 4-6, when Kazakh hunters gather in the westernmost province of Mongolia for the Golden Eagle Festival. Mounted on elaborately-decorated horses, and brandishing keen-eyed eagles with seven-foot wingspans, these burly bearded men (and the occasional woman) compete in hunting, horseracing, and kokbar: a horseback tug-of-war. Most tours of Mongolia start and finish in the capital city of Ulaanbaatar, where you should catch a traditional throat-singing performance at Tumen Ekh Song and Dance Ensemble (nightly at 6pm). And don’t leave the city without swinging by the Kempinsky Hotel for a glass of bubbly, and a plate of the local delicacy: Khuushuur (pan-fried dumplings).

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