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Introducing the artists, foragers, pirates and shrine-builders who populate quirky small towns across the U.S.

No. 3 Ithaca, NY

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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.

America's Quirkiest Towns

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.

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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.”

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