The 20 Quirkiest Cities in America

To Caitlin Sandburg, her hometown of San Francisco provides a safe haven—for oddballs. “Once you’ve been here long enough, nothing surprises you,” says the hospitality exec. “Whether it’s a naked person walking down the street, someone dressed in full drag, or ‘Burning Man’ types, no one really raises an eyebrow. Being a freak here is so normal.” Even so, according to Travel + Leisure readers, there are five cities in the nation that have more weird people than the City by the Bay. In this year’s America’s Favorite Cities survey—in which readers ranked 38 cities for features such as romance, thrift shops, craft beers and, indeed, quirky locals—the results show how a city can be nicely shaped by its kookiest denizens. One top five city, for instance, offers a hotel fashioned out of a former psychiatric hospital and donuts sprinkled with faux meth. Another winner is famed for its offbeat bars—like the one decorated for Christmas year round, or another that regularly holds armadillo races. Onward, to the cities with the most kooks per capita.

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20. Atlanta

They may not be perceived as showy—readers sized them up as being both hip and aloof—but Atlantans are increasingly coming out of their shells, at least for a good parade. The annual Lantern Parade—part of September’s Art on the BeltLine exhibit, along the revamped railroad corridor—attracts some 20,000 lantern-toting participants. Despite the evening parade, the well-dressed locals seem to be morning people, since the city ranked well for both diners and brunch. For a quirky, only-in-the-South brunch, try the West Egg Café, which serves breakfast all day on Sundays (dubbed Brinner in the evening) and on Friday nights offers amazing chicken-and-waffle variations—with, say, pimento cheese and bacon or habanero-infused maple syrup.

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19. Louisville, Kentucky

America's Quirkiest Cities: No. 19 Louisville, KY — © Sniper Photography

The Kentucky city may be a newcomer to the list, but it’s giving other weird cities a run for their money. For starters, this is the birthplace of the annual Lebowski Fest, the now-national celebration of the Coen brothers cult-favorite bowling film. To bowl on your own, go to Vernon Lanes, which has been a local hangout for more than a century and (with 300 bourbons on the menu) is a stop on the Urban Bourbon Trail. The city also ranked well for burgers; at Game, you can choose among patties made of kangaroo, antelope, or wild boar. In the case of Louisville, quirky does not equate with cluttered: the city also made the top 10 for feeling clean.

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18. Philadelphia

Some might say there is something odd about a city that honors a big, broken bell—but Philadelphia thrives on history, and not just the kind associated with the founding fathers. You can appreciate the old, abnormal body parts on display at the medically oriented Mutter Museum or the creepy walkways of the Eastern State Penitentiary (once home to Al Capone), where you can also take the kids on a fun scavenger hunt. The city’s nerve center for local quirky types, though, is Fishtown, where you’ll find a nice example of why Philly won the bronze medal for pizza: Pizza Brain has pies like the oddly named Felix Huppert (Gruyère and caramelized onion) and the Buffy Ernst (blue cheese and Buffalo wing sauce), and a collection of pizza-themed vinyl records. Readers felt that Philly locals embody an ironic combination: loving sports without seeming to be athletic themselves.

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17. Los Angeles

In this show-business town, you need to stand out to get ahead—like the buff exhibitionists in Venice or the spendy fashionistas in Beverly Hills. Even the highly ranked bakeries hustle to set themselves apart: at Gjusta, in Venice, you can pick up baklava croissants (Cronuts are so last year) and rabbit terrines. Otherwise, readers applaud L.A. for its nightclubs and wild weekend atmosphere. Hot nightlife hubs these days include the ’70s-themed bar Good Times at Davey Wayne’s in Hollywood and artisanal-cocktail-rich The Edison, located in downtown’s former power plant. For another version of “wild,” don’t miss the performance art going on at the Hollywood Forever Cemetery, which is also the final resting place of stars like Rudolph Valentino and Estelle Getty.

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16. Nashville

Before this Tennessee city was the country-music capital, it had a classical bent—as in, ancient Greece. The city’s Parthenon—built in 1897 and filled with American paintings—may seem a little out of place here, but it’s also the only full-scale replica of the Greek Parthenon in the world. And while Music City has had an increasingly broad definition of museums since then (like the memorabilia-lined restaurant Cooter’s Place, paying tribute to The Dukes of Hazzard), the city has also generated plenty of museum-worthy legends—like the late George Jones, whose own museum will open here this spring. Readers also loved the city’s dive bars, like Santa’s Pub—located in a trailer near the fairgrounds and run by a guy who looks like another legend. Speaking of jolly, Nashville locals ranked as some of the most affable people in the U.S.

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15. Houston, Texas

America's Quirkiest Cities: No. 15 Houston — © Houston Zoo/Stephanie Adams

Compared to nearby Austin, H-Town doesn’t get much credit for its weirdos. But just like folks in the state capital, locals in Houston love to gather at sunset to watch swarms of bats: here, you can see them from the banks of Buffalo Bayou, as they fly out from under Montrose’s Waugh Drive Bridge. While readers gave Houston high marks for its impeccable art collections, you could also commission a unique painting here—created (with only a little help) by an elephant, jaguar, or white-faced saki at the Houston Zoo (just take note that the $250 painting will take up to six weeks for the critter to complete). To see why the city also ranked well for its distinctive, high-end shopping, try on a pair of one-of-a-kind boots from Tejas Custom Boots on Westheimer.

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14. Portland, Maine

World's Friendliest Cities: Portland, Maine — Courtesy of Greater Portland Convention & Visitors Bureau

If one feels the need to “put a bird on it” in Portland, then this city will, no doubt, put a lobster on it. Holy Donut has stretched the definition of the lobster roll by offering a lobster-stuffed donut, as well as making donuts with potatoes—which promise not to give you that post-cruller hangover. While readers indeed loved Portland’s nonthreatening vibe, the locals seem drawn to what may be lurking in the shadows: downtown’s International Cryptozoology Museum highlights mysterious creatures like Bigfoot, abominable snowmen, and the thylacine, a rare carnivorous marsupial. Any weirdness aside, the locals are all business behind the wheel, ranking near the top for their driving skills.

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13. Pittsburgh

Andy Warhol’s hometown still turns out its artistic rebels—like Randy Gibson, whose Randyland home, in the city’s Mexican War Streets district, is an art lovers’ magnet with its colorful murals and courtyard. For provocative dining, check out Conflict Kitchen, which serves only cuisine from countries with which the United States is at odds (like North Korean kimchi or rumaniyya, a Palestinian eggplant, lentil, and pomegranate stew). Readers, meanwhile, were perhaps dazzled by the bravado of Steelers fans in this sport-loving town; you can commune with them at Sunny Jim’s Tavern in the Kilbuck area, which boasts of having the world’s largest outdoor TV (25 feet) and does occasional recliner giveaways.

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12. Minneapolis/St. Paul

People who will cycle to work in the depths of winter—and the Twin Cities ranked near the bottom of the survey for its weather—are clearly comfortable with a contrarian lifestyle. Even the cities’ highly ranked burgers—called Juicy Lucies—buck convention by offering cheese inside the patty. And while readers applauded Minneapolis/St. Paul for its theater scene, one unexpectedly compelling venue is Bryant Lake Bowl, which offers storytelling, dance, and poetry alongside the bowling lanes. The hipster-rich Twin Cities also ranked in the top 10 for its cool diners, but here you won’t just find traditional greasy spoons: Tiny Diner, in the Powderhorn neighborhood, is supplied by its own Tiny Farm and also offers aspiring-farmer events like “Insects We Love” and “Functional Fungi.”

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11. Tampa, Florida

America's Quirkiest Cities: No. 11 Tampa, FL — © EventFest – Tampa

The NFL’s Buccaneer mascot is no joke in this Florida city, new to the survey this year. Gasparilla season — with parades and festivals celebrating the city’s centuries-old pirate history — lasts throughout the winter, but year round, you can embrace the swashbuckling spirit at Gaspar’s Grotto, offering a $25 “bucket of grog” (read: a huge margarita) to share with friends. To explore one colorful chapter in the city’s history, go to Ybor City — once known as the cigar capital of the world — and visit the two remaining stogie factories, J.C. Newman and Tampa Sweethearts.

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10. New York City

New York’s top 10–ranked transportation system exists mostly under the streets, and indeed the city’s most eccentric characters—aside from the strolling, cartoonish ones in Times Square—also have an underground charm. To admire folks who were freaky before freaky was cool, you can’t go wrong with the contortionists and fire-eaters of the Coney Island Circus Sideshow. In the survey’s No. 1 city for culture, museums, and theater, meanwhile, you’ll also find the Earth Room (a dirt-filled gallery in SoHo), the lift-loving Elevator Historical Society Museum in Queens, and the sports-meets-performance-art of competitive Ping-Pong at Spin, in the Flatiron District. No surprise, the Big Apple also ranked at No. 2 for vivid people-watching.

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9. Seattle

The Washington locals did not light up the survey for being friendly, but perhaps they just don’t care about impressing others—as in, other people. In a city where, according to census numbers, dogs outnumber children, your best bet for good vibes may be to follow the four-footed crowd. In the Fremont area—known for its giant stone troll, the regularly decorated Lenin statue, and the nude cyclists who ride during the summer solstice—you’ll also find Norm’s Eatery & Ale House, where dogs are welcome to join you at your inside table. The city also scored well for specialty food shops like the bountiful Pike Place Market—as well as places like Scraps Dog Bakery in South Lake Union, where you can indulge your furry friend with gorgeous baked treats and pup-size Seahawks swag, the latter reflecting the locals’ well-known love of their teams.

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8. Kansas City, MO

These midwesterners may have struck readers as thrifty and no-nonsense, but that doesn’t make them dull. The city ranked highly for both its museums and its sense of history—though some of that history is distinctly outside the box. Take The 1950s All-Electric House, which was originally built to be a glimpse of the future (when everyone, for instance, would have electric curtain openers). Or you can explore the Arabia Steamboat Museum, where you can see a fascinating array of pre–Civil War artifacts, recovered 132 years after the boat sank in the Missouri River. The city also ranked in the top 10 for its coffee, exemplified nicely at Oddly Correct, where cream and sugar are verboten.

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7. Baltimore

The city known for its own quirky dialect—the “Hey Hon”–heavy Bawlmerese—has long celebrated its own outsider status. The American Visionary Art Museum, for instance, shows a wide range of outsider art (like the broken-glass-and-glitter rendition of George Washington by “Baltimore Glassman” Paul Darmafall. To hang out with literary oddballs, go to Atomic Books, in the Hampden neighborhood, where director and native son John Waters picks up his fan mail; you can people-watch at Eightbar, a bar in the rear of the bookstore with craft beer and gourmet soda. To see why the city also ranked well for food trucks, don’t miss the bibimbap from one local favorite, the Korean-fusion Koco Truck.

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6. San Francisco

The city that gave the world hippies and the Castro also scored highly in the survey for fabulously fashionable locals. To see them up close, take the hipster-led Wild SF Walking Tour through the Beat Generation’s North Beach and the artsy Mission District. Not surprisingly, San Francisco scored in the top five for its wine bars and cocktail lounges—but even those can offer their own surprises. Take the San Francisco Champagne Society, a reservations-only lounge in SoMa that serves small-production bubblies, or The Interval, at Fort Mason Center, which has “timeless” cocktails (like an Aged Tom Collins) and a clock designed to last 10,000 years, installed by a local group called the Long Now Foundation.

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5. Albuquerque

The New Mexico city made the top five for its unique, piñon-accented coffee—which tastes great with a faux-meth-sprinkled Blue Sky donut at Rebel Donuts. Indeed, the sometimes-dubbed Albuquirky has embraced its links to the TV series Breaking Bad: you can explore Walter White’s version of the city in ABQ Trolley’s Bad Tour. Otherwise, you could stay at the Hotel Parq Central, a former psychiatric hospital that now has the rooftop Apothecary Lounge, with pre-Prohibition cocktails and a full selection of interesting bitters, like blood orange, celery, and Aztec chocolate. The city also ranked in the top 10 for being both adventurous and affordable.

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4. Providence, RI

Founded by the tolerance-advocating Roger Williams, the Rhode Island city has long cultivated iconoclasts. Indeed, you’ll find more than a mere symphony and theater scene here: you can experience the all-puppet Big Nazo Theater (where you can get hands-on with the alienesque creatures) or the Extraordinary Rendition Band, a local marching band featuring sousaphones, accordions, and washboards. The city ranked highly for both its burgers and its sandwiches, but its only-in-Providence hot dogs also distinguish themselves: at Olneyville New York System (which does not presume similarity with New York dogs), the savvy order is “three all the way with coffee milk,” which comes with everything (meat sauce, mustard, chopped onion) and a glass of the odd but wholesome state drink. Say what you want, but the locals did not rank as being dumb, either.

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3. Portland, Oregon

America's Quirkiest Cities: No. 3 Portland, OR — © Michael Branscum

The legendary community of hipsters ranked at the top of this year’s survey for being pedestrian-friendly—and perhaps, by association, unicycle-friendly, too. The independently minded locals are known for their passion for sourcing: the store MadeHere PDX boasts all local (and often kind of bizarre) products, like mustache wax or a wood-and-leather six-pack holder for cyclists. Readers also awarded Portland the top spots for its tasting-room coffee (like Coava) and craft beer (like the inventive brews at Coalition Brewing), but the City of Roses even offers a tasting-room experience with salt. At Jacobsen Salt (which shares space with the artisanal honeys of Bee Local), you can sample, say, the Smoked Cherrywood or Stumptown Coffee Flake salts. Unicycling is clearly good for your core: the locals also ranked No. 3 for being buff.

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2. Austin, Texas

America's Quirkiest Cities: No. 2 Austin, TX — © Austin Convention & Visitors Bureau

The 1991 film Slacker—by Boyhood’s Richard Linklater—featured aimless intellectuals wandering the Texas capital, and you can still find a lot of those same folks (perhaps literally the same folks) populating the bars, food-truck pods, and parks of Austin today. The newest incarnation of the Keep Austin Weird motto is the recently opened Sfanthor on South Congress—a wax museum celebrating the greatest in the sci-fi, fantasy, and horror genres (hence, “Sfanthor”). To experience some of the weirdest of Austin’s highly ranked bars, order a Shiner beer at longtime standouts like the always-decorated-for-Christmas Lala’s, or Little Longhorn Saloon (home of the weekly Chicken-S--- Bingo)—or the newer entries, like Javelina on Rainey, which hosts live armadillo races.

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1. New Orleans

The city known for its jubilant funerals, voodoo shops, and seemingly nonstop festivals—from the roller-derby-based San Fermin Festival to the Oak Street Po’ Boy Festival—was a shoo-in to win the quirky category. Indeed, the offbeat culture is so dominant that it’s become mainstream: even the spa at the Ritz-Carlton offers a VooDoo Massage, complete with chants and scents of absinthe. To experience the city in a quirky but convivial way, try one of the NOLA Social Rides—like the organized bike ride starting at Congo Square, with stops to hear live music. New Orleans also made the top five for two things that make travelers giddy: romance and free attractions.

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