Jeremy Swanson

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

No. 6 Aspen, CO

6 of 21

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.

America's Quirkiest Towns

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.

Jeremy Swanson

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.”

Promoted Stories
Explore More
More from T+L