America's Quirkiest Towns
Paul Stone loves the colorful locals he sees on Boulder, CO’s downtown plaza, the no-cars-allowed Pearl Street Mall. “There’s even one very flexible man,” says the real estate agent, “who is about six feet tall, but can fold himself into a little box.”
Home to street performers, students, and spandex-clad athletes, “Boulder attracts a wide variety of people who live together in harmony,” says Stone. That double-jointed blend is probably why the Colorado mountain town also made the top 20 for quirky locals, according to Travel + Leisure readers.
They ranked hundreds of towns for such magnetic qualities as vibrant main streets, coffee bars, and an eco-friendly vibe. And while plenty of those features may contribute to a town’s unique personality, the top 20 winners in the quirky category take it a step further. One highly ranked town is an unlikely hotbed for Tibetan monks, while another largely forgoes Valentine’s Day to celebrate Charles Darwin instead.
Asheville, NC, for instance, ranked highly for its booming craft beer industry and diverse dining scene—but here, “diverse” goes well beyond a few good places to eat pho. On his No Taste Like Home tour, Ashevillian Alan Muskat lets visitors forage in the woods for—and then sample—wild local delicacies like “fairy potatoes,” which grow on vines, and reishi, known as the Mushroom of Immortality.
“Asheville sits smack in the middle of the most biodiverse temperate bioregion on the planet,” Muskat boasts. “So even our plants are freaky.”
No. 1 Asheville, NC
Is it the thinner mountain air or that the locals are standing too close to a vortex? Either way, these North Carolinians are tops for eccentricity thanks to both old and new charms: the vortex-laden terrain, which purports to send off good energy; the Friday night drum circle in downtown’s Pritchard Park; and the seemingly bottomless love of local beer. To tap into their vibes, try the beer-and-moonshine “hoptails” at Grove Park Inn’s Great Hall Bar, the BRÖÖ shampoo at the Earth Fare shop, or the port cake at Short Street Cakes. Asheville also ranked in the top 10 for great bakeries; Vortex Doughnuts offers a local beer-of-the-day donut.
No. 2 Provincetown, MA
With its history of artists and theater types—Eugene O’Neill, Al Pacino, and Barbra Streisand all cut their teeth here—Provincetown has always provided a colorful contrast to the otherwise seersuckered Cape Cod. For a suitably quirky place to stay, check in at the Salt House Inn, where each room has a “wall of curiosities” featuring vintage art or interesting objects found along the beach. The longtime gay-friendly destination also impressed readers with its seafood shacks (such as the Red Shack, which does Mexican and Moroccan lobster rolls) and cool souvenirs, such as a photo of your aura, done by Whaler’s Wharf psychic Carolyn Miller.
No. 3 Ithaca, NY
This upstate New York college town has deep hippie roots—it’s the home of legendary vegetarian restaurant Moosewood—but these are not your typical flower children. Come February, instead of celebrating Valentine’s, the town makes a big to-do over Charles Darwin’s birthday, in its Darwin Days. Thanks to the area’s Cayuga Wine Trail, Ithaca also scored in the top five for vino. Start your taste testing with Six Mile Creek, which uses grapes even for distilled spirits like its Chardonnay-based gin.
No. 4 Boulder, CO
This lovable mountain town is so outdoorsy (and granola) that each July, locals hold a Tube to Work Day. And while Colorado has recently become more famous for its smokable “herbs,” you can still explore the town’s original herbal high on a free tour of the Celestial Seasonings tea factory, or sit down for afternoon tea and samosas at the elaborately hand-carved Boulder Dushanbe Tea House, originally built in Boulder’s sister city in Tajikistan. To see why the town also ranked well for burgers, check out the grass-fed wonders at The Sink, which is completely wind-powered.
No. 5 Lambertville, NJ
To folks in this quaint town along the Delaware River, the real weirdos may be the motorcycle riders and Wiccans across the bridge in New Hope, PA. Still, these Jersey denizens—artists, gardeners, and perhaps actors gunning to play General Washington in the next historical reenactment—get props for their serious attitude toward antiques. The four-story People’s Store has been selling treasures since 1832 (when such things weren’t old). For people-watching, go to coffee and gourmet shop Lambertville Trading Company, where the java is old-school, too: iced coffee served with frozen cubes of coffee and a full range of bone-china mugs.
No. 6 Aspen, CO
This tony Colorado ski town attracts more than just the designer snowsuit crowd. Check out Woody Creek Tavern, one of Hunter S. Thompson’s favorite hangouts, with its sensory-overloaded walls of newspaper clippings and children’s art. Residents have a soft spot for pet lovers: the local shelter’s Rent-a Pet program lets you visit with a designated cat or dog during your stay. Aspen also ranked well for its sense of adventure, which can extend from outdoor sports to food and drink. At Zocalito’s, you can order your guacamole with chapulines (grasshoppers), and at Hotel Jerome’s J-Bar, be sure to try an Aspen Crud, the bourbon-laced milkshake cocktail that dates back to Prohibition.
No. 7 Fayetteville, AR
Whether you chalk it up to kookiness or school pride, this college town celebrates New Year’s each year with its own Hog Drop. The home of the University of Arkansas Razorbacks also ranked well for its sense of history: at the Clinton House Museum, you can stand in the modest little home where the former president and secretary of state once lived (and even got married, in the living room). To feel even more like an insider, stay at the Inn at Carnall Hall—an elegant hotel built from a rehabbed women’s dorm—and tuck in at one of Fayetteville’s high-ranking diners, such as the Rolling Pin Café, where on Saturdays you can order your biscuits with chocolate gravy.
No. 8 Charlottesville, VA
Thomas Jefferson certainly had his share of eccentricities, and his old stomping ground has carried on the tradition. The hometown school, UVA (which helped the town rank well for its techy factor), was the alma mater of Edgar Allen Poe, and his dorm room is still preserved behind glass (and no, there doesn’t seem to be a beating heart underneath the floorboards). The town also got high marks for its barbecue—such as the brisket and ribs at Buttz BBQ—but you might see even more local eccentrics at Holy Cow, a vegan restaurant that does a barbecue version of the mythic jackalope (in this case, jackfruit).
No. 9 Bloomington, IN
No one knows exactly where the term Hoosiers came from, but these proud Indianans embrace the idea of being a little unpredictable. After all, the midwestern town has been a hotbed for Tibetan Buddhists for decades. You can stroll the gardens at the Dagom Gaden Tensung Ling Buddhist Monastery, or explore the Tibetan Mongolian Buddhist Cultural Center, established by the Dalai Lama’s eldest brother. To eat like a Tibetan, try the steamed-dumpling momos at Anyetsang’s Little Tibet. And to see why the college town also excelled in beer, check out Upland Brewing Company, popular for its patio, live music, and fabulous sour lambics.
No. 10 Sonoma, CA
Readers love this wine country town because it hasn’t gotten too posh: you’ll still find historic sites, such as General Vallejo’s house from the 1850s, along with contemporary local eccentrics such as the Dancing Jogging Lady, who has her own Facebook fan page. Sonoma also ranked in the top 10 for its adobe town square—lined with a dozen-plus wine-tasting rooms—as well as its coffee. A good place to hang with the locals is The Epicurean Connection, a café right off Sonoma Plaza that offers local wine, cheese-making classes, and goat-milk lattes.
No. 11 Burlington, VT
This town on Lake Champlain gave the world the ultimate quirky college band (Phish) as well as Ben & Jerry’s, which started here in a former gas station—and no doubt helped Burlington rank highly in the survey for ice cream. It also scored well for cool souvenirs—like the locally made maple syrups and stuffed Hugg-a-Planets at the Peace and Justice Store—and wine, such as the bottles from East Shore Vineyard. For something quirkier, check out the tasting room for Citizen Cider, which features artisan alcoholic ciders including the AmeriCran, made with fermented cranberries.
No. 12 Lewisburg, WV
Any town that names its own performance space Carnegie Hall has confidence, and indeed this Greenbrier County town also scored well in the survey for civic pride. The mountain town’s Civil War past—1862’s Battle of Lewisburg, which the Union won—delivered big points in the history category, and it also ranked highly for historic inns like the General Lewis, which is filled with antiques, Civil War–era tools, and a resident ghost. Come in autumn to join the Zombie 5K, which invites runners to zombie-fy themselves and chase others for motivation. Lewisburg also impressed readers with less-threatening festivities like April’s Chocolate Festival.
No. 13 Tiburon, CA
Once a rowdy railroad town, this Marin County community evolved into an upscale enclave for San Francisco transplants. But walk along its main street and you can explore Ark Row, comprising stores built out of old houseboats. To lounge with the locals—and get great views of the skyline, Angel Island, and Alcatraz—go to the deck of Sam’s Anchor Café, once a hangout for bootleggers (you can still see its escape-route trap door, leading to the water below).
No. 14 Doylestown, PA
In the heart of history-rich Bucks County, there’s a fine line between quirkiness and extreme quaintness: cutting-edge souvenirs include the locally grown sachets from the Peace Valley Lavender Farm. Doylestown also ranked well for its fairs, such as the annual Polish Festival, held at the National Shrine of Our Lady of Czestochowa (a Black Madonna sometimes seen as a subversive), and the crowd-pleasing Beer Fest, held at the town’s former estate, Fonthill Castle. Readers also applauded Doylestown for brunch: try the Purgatory Plate (poached eggs over slow-cooked sweet onions, plum tomatoes, and Grana Padano cheese) at local favorite Domani Star.
No. 15 Lawrence, KS
This Kansas town made the top 20 for embracing those who aren’t afraid to make public spectacles. Each summer brings the Lawrence Busker Festival, featuring sword swallowers and fire dancers, and every Christmas the fire department makes a show of rescuing Santa off the roof of Weaver’s Department Store. Year round, Lawrence supports the Museum of the Odd, whose curator has collected such fascinating exhibits as celebrity toothbrushes, ashtrays made from animal limbs, and roughly 600 sock monkeys. It also ranked highly for its ice cream, such as the cookie-and-candy-filled Kansas Twister scoops at Sylas and Maddy’s.
No. 16 Snowmass, CO
This ski town landed in the survey’s top 10 for being friendly and smart, but quirky isn’t too far behind. After all, it seems locals have a habit of attaching stuff to trees. The Sanctuaries in the Snow tour, led by a retired attorney, will take you to see the area’s best mysterious shrines—elaborate homages in the woods devoted to, say, Jerry Garcia, golf, or Snoopy. Past quirky residents, meanwhile, have included at least one woolly mammoth; a tusk was excavated a few years ago in Snowmass Village and can now be seen, along with other local fossils, at the town’s Ice Age Discovery Center.
No. 17 Greenville, SC
The most iconic site in this Blue Ridge town is truly off-kilter: Liberty Bridge, in Falls Park, a pedestrian bridge whose 90-foot-tall masts tilt an eye-catching 15 degrees. If you’re not feeling woozy afterward, stop in at the Dark Corner Distillery, the state’s first legal moonshine operation, where you can taste the Butterscotch Shine or the chipotle-and-cinnamon Hot Mama, and learn to make your own hooch back at home. Readers also liked the casual dining scene: at Papi’s Tacos, the off-the-menu favorite is the Walking Taco, a loaded bag of Doritos and a fork. Locals may enjoy it ironically, since Greenville also placed in the top 10 for being hip.
No. 18 Franklin, TN
This charming town south of Nashville dances to it own beat, winning the survey for its un-countrified festivals, such as its summer Jazz Festival and winter’s Dickens of a Christmas. Franklin also won the survey for its cool souvenirs. You might go home with bottles of brisket marinade and denim coozies from Puckett’s Grocery, or rare volumes from Landmark Booksellers, whose building dates back to 1798 and reportedly houses some busy ghosts. Around here, that’s not so unusual: Franklin’s present-day locals scored well in the survey for staying active.
No. 19 Amelia Island, FL
There’s a fickle backstory to this little island town: it has belonged to eight different nations, and today offers a fun-loving blend of Deep South and island culture. The town ranked highly in the survey for historic inns like the Victorian-era Hoyt House and Williams House and for its family-vacation appeal. For a one-of-a-kind activity with the kids, take Amelia River Cruises’ Eco-Shrimping Tour, where you get to catch (then release) the little shellfish.
No. 20 Beaufort, NC
While some towns do Civil War reenactments, Beaufort does an annual re-creation of a 1747 showdown between pirates and feisty town locals. That swashbuckling sense of excitement still lives on. Readers loved this Inner Banks town for its romantic places to stay—such as The Cedars Inn, which has hosted seafaring types as far back as the late 1700s—and its live music. To hear the best local musicians, go to the Backstreet Pub, where Wednesday nights are “Hoot Nights,” and during downtimes, patrons are welcome to play cribbage at their tables.