This four-day fest, which includes a 24-hour climbing competition in the backwoods of Arkansas, mixes the high jinks of Coachella—parties, costumes, free haircuts, live music—with the awesomely pointless task of climbing as many routes as possible in a day. One of climbing’s most authentic events, Horseshoe Hell is all about fun, camaraderie, and—with arms burning and hands raw—a fair bit of pain.
Old Forge, NY
After three decades, this 90-mile, three-day stage race through New York’s Adirondack Mountains has indeed become a classic. Following routes first traveled by early settlers, paddlers trace tannin-stained lakes, three rivers, and five miles of portages through a wilderness inhabited by moose, bears, and coyotes. It’s technically a race, but laid-back participants may be lured from their boats by small-town bars and ice cream stands.
San Francisco, CA
It’s a little ironic that one of the country’s most beautiful trail races overlooks one of its largest and most populated cities, but the wind-scoured Marin Headlands aren’t your average urban playground. Just across the Golden Gate Bridge from San Francisco, they rise up 800 feet from the Pacific, offering racers a heady, challenging, view-packed run past the wildlife-saturated lagoon near Rodeo Beach and historic military installations.
A gran fondo in the Centennial State sounds about as challenging as you could ask for, but this one starts in the town of Telluride, high in the San Juan Mountains, and heads downhill for nearly its entire length, passing yellowing aspens, deserted mining camps, and red-rock canyons on its way to the desert of western Colorado. As if the scenery weren’t enough, registration also includes a postride lunch, beers, and live music.
Port Arthur, Tasmania
At the bottom of the world, the Australian state of Tasmania is renowned for its raw beauty and long-distance treks (they call them “bushwalks”), the newest—and perhaps most spectacular—of which is the 29-mile Three Capes Track. Edging along some of the world’s highest sea cliffs almost 1,000 feet above the Southern Ocean, the track is remote, wild, and, thanks to a trio of fully outfitted huts, comfortable.