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.