They're Weird and Proud: America’s Quirkiest Cities

The Mermaid Parade at Coney Island in New York. (Courtesy: Coney Island USA)

By Katrina Brown Hunt

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, someonedressed 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 doughnuts 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.

See the rest of America’s Quirkiest Cities

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.

9. Seattle

(Photo: Jake Stangel)

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.

8. Kansas City, Mo.

(Photo: Carlos Lima)

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.

7. Baltimore

Atomic Books (Photo: Pete Prodoehl/Flickr)

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.

6. San Francisco

(Courtesy: Wild SF Walking Tours)

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.

Related: 8 Wonderfully Weird Museums in Philadelphia

5. Albuquerque

(Photo: ABQ Trolley Co.)

The New Mexico city made the top five for its unique, piñon-accented coffee—which tastes great with a faux-meth-sprinkled Blue Sky doughnut 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.

4. Providence, R.I.

(Courtesy: Extraordinary Rendition Band)

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.

3. Portland, Ore.

(Photo: 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.

2. Austin, Texas

(Courtesy: 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-Sh*t Bingo)—or the newer entries, like Javelina on Rainey, which hosts live armadillo races.

Related: Weird, Wild Stuff to Be Found in Austin

1. New Orleans

(Photo: Donna Kennedy - La Petite Photography)

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.

More from Travel + Leisure:

T+L’s Guide to Having Fun on a Business Trip

America’s Quirkiest Towns

America’s Snobbiest Cities

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