Because of Oktoberfest, a lot of travel writers are going to recommend Munich as the top city for you to visit in October. Not this one. This is because it’s more useful to you, reader, to read about destinations that haven’t already occurred to you, and not at all because my one Oktoberfest experience ended in police custody -- something to do with fighting strangers barefoot in traffic -- and a still-unpaid fine that I’ve been successfully avoiding for the last four years through the canny strategy of not going back to Germany. You may think this reflects poorly on me, but I haven’t yet told you the most important detail, which is that none of it was my fault. And anyway, Oktoberfest is more of a season-long thing, not even really specific to October, which happens to be a pretty great month to travel. Summer surge pricing has given way to off-season discounts. The air is finally crisp in the places it was previously swampy, but not yet too cold. And fall festivals -- pleasant or otherwise -- are in full swing. It is time to travel somewhere new. Here are a few of the most cheery, spooky, ~autumnal~ places to be right now.
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If you want a Halloween for the ages, you can’t do better than Transylvania, a region that leans all the way to its brand come October. There are costume parties in medieval castles and tours themed around Count Dracula and Vlad the Impaler. Pay a visit to Bran Castle -- Dracula’s castle, rather -- to get the full experience. Head into Bucharest and day-trip to medieval Saxon towns like Brașov (where there is also an Oktoberfest; go with my blessing). For those who wish to go all out (all in?), there are Halloween packages that’ll arrange you the spookiest possible itinerary.
Negril is a resort town at Jamaica’s western tip, the part that houses its famous Seven Mile Beach -- the very best stretch of coastline the island has to offer. Late October is a sweet spot when hurricane season is wrapping up and the weather’s on its way to peak pleasantness, but peak winter tourism has not yet arrived, meaning you won’t spend your time at the beach battling crowds. Try Azul Beach Resort if you want an all-inclusive option in the area, and take a boat over to the world-famous Rick’s Cafe, where you can eat, drink, and jump off a cliff all in one go. Head into Kingston for the Jamaica Food & Drinks Festival, from October 26 through November 3. Under no circumstances should you leave the island without eating several meals’ worth of ackee and saltfish.
Atacama Desert, Chile
October is springtime down here, and the ideal time to visit the bone-dry Atacama Desert. The thin, moisture-less air makes it perfect for stargazing, which is why the European Space Agency chose to house an array of their cutting-edge telescopes here. Look for a tour that includes a sunset hike to the top of the Moon Valley sand dunes; it feels like you’ve landed on another planet, especially if you spot one of the ESA’s Mars rovers rumbling along on a test-drive. Stay in nearby San Pedro for easy access to the flamingo-speckled salt flats.
Rapid City, South Dakota
October 11-13 marks the annual He Sapa Wacipi, also known as the Black Hills Powwow. Thousands of spectators turn out to watch what’s grown into a marquee Native American cultural event, with athletic competitions, singing, dancing, drumming and the He Sapa Win pageant. On October 14, celebrate Native Americans’ Day; South Dakota is the first state to formally institute the holiday in place of Columbus Day. Rapid City itself, a treasure trove of public parks and monuments, is a fantastic base from which to explore the Black Hills, the Crazy Horse Memorial, and the Badlands. Also, peak foliage! Take a drive along the Peter Norbeck National or Wildlife Loop scenic byways.
Just like in Jamaica, late October is a sweet spot between hurricane season and tourist season. The four US Virgin Islands (St. Thomas, St. John, St. Croix, and the newer, lesser-known Water Island) have made unbelievable strides recovering from 2017’s one-two punch of hurricanes Maria and Irma, and spending your tourism dollars there is mutually beneficial to all involved. St. Thomas is the destination for all pirate-related activities, and when you’re done checking out Blackbeard’s Castle, stop for a waterfront drink at Abi Beach Bar. The legendary trade winds keep the water perfect for swimming. MORE: This year, the US Virgin Islands are welcoming visitors like never before
September to May is aurora borealis season in Canada, and there’s nowhere better to peep those solar flashes than in Alberta, at the Jasper Dark Sky Festival, which runs from October 18-27. Jasper has so little light pollution it’s been recognized by the Royal Astronomical Society of Canada, and the festival draws leading astronauts and physicists from the science community each year. If you stay at the Fairmont Jasper Park Lodge, you can get a special Dark Sky discount. During the day, make sure to get out there and explore those gorgeous Canadian Rockies you’ve heard so much about. Who knows, maybe you’ll like Canada so much you’ll want to move there.
If you’ve only been considering Lisbon, now is the time to change that. Aside from getting to wander the sea cave-studded coastline, if you visit Porto in the first half of the month and you’ll be there for grape-stomping season -- and we’re talking about the old-school, barefoot, do-it-while-singing-traditional-folk-songs kind of grape stomping here. The end goal, obviously, is to make port -- you can try previous vintages at Quinta da Roêda, or any of its neighbors in the Douro Valley Wine Region. Grape-stomp with your friends, grape-stomp with strangers, but most importantly grape-stomp while drinking. Port, of course. Always port.