Jackson Hole first allowed skiers and boarders to exit its boundaries in 1999, putting it at the forefront of the sidecountry/backcountry boom that's happened in the past decade. If you're traveling out of bounds, you'll want a guide to help you navigate the steep avalanche terrain. Contact the resort's Jackson Hole Alpine Guides. They have seven UIAGM-certified guides on their staff and over 100 years of combined guiding experience.
The guides offer customized trips, but they mostly you'll use Jackson Hole's iconic Tram to climb the 4,139 vertical feet up Rendezvous Mountain where they exit the ski area through the backcountry gate. From there, they'll take you through bowls, steep chutes, and couloirs, some of which you'll have to rappel into. Expect to wind up back at the Tram base where they'll cut you to the front of the line. How much climbing you put in depends on your fitness and your skill. "If you can't walk to the fifth floor of your office in New York City, it'll be a more vertical with less traversing," says operations manager and guide Eric Henderson. "The better shape you're in, the better experience you'll have."
$695 for a group of two; jacksonhole.com