Cowboycation

Ride Into the Heart of the Tetons

Step into your boots—this is where the West gets real. In Jackson Hole, cowboy culture isn’t kitsch. It’s legacy. At Caldera House, we believe there’s no better way to connect with the spirit of the valley than by embracing its Wild West roots. Whether you’re riding through golden meadows on horseback, sipping whiskey by the fire, or watching a bronc rider hang on for dear life at the Jackson Hole Rodeo, the West lives on—and it’s waiting for you.

Your cowboycation begins with a custom trail ride through the Gros Ventre wilderness. Led by a seasoned local wrangler, this private outing winds through scenic aspen groves, sagebrush flats, and mountain overlooks that feel like film stills. Keep your eyes peeled for pronghorn, elk, and eagles soaring overhead. Want to take it up a notch? Our concierge can arrange a multi-hour backcountry ride complete with a riverside picnic curated by our chef.

Come evening, dust off and head to the Jackson Hole Rodeo, a summer tradition since 1890. Bull riding, roping, and barrel racing unfold under neon lights with the Tetons silhouetted in the background. We’ll handle VIP tickets, transport, and a little something for your flask if you’d like.

Still looking to live out your Western fantasy? Consider a visit to a working ranch, where you can tour stables, learn to rope, or watch a cutting horse demonstration. Or try your hand at fly fishing—a different kind of cowboy pursuit—on a drift boat adventure down the Snake River. Prefer to stay grounded? Saddle up with a private archery lesson or axe throwing experience tailored for your group.

Back at the House, return to modern comforts with frontier flair. Trade your boots for a robe and book a massage at our in-suite spa. Recount the day’s stories over small-batch bourbon in the Alpine Lounge, or gather your group for a chef-prepared fireside dinner in your private suite. This is Jackson Hole the Caldera way—rugged, refined, and unforgettable.

Day 1: Welcome to the West

Morning Arrive at Caldera House and check into your suite. Take in the mountain air with a welcome drink in the Alpine Lounge.
Afternoon Explore Teton Village or stroll to the base of the tram for your first look at the Tetons. Archery or axe throwing session arranged by the concierge.
Evening Casual dinner at Corsa. Nightcap on your private terrace under the stars.

Day 2: Saddle Up & Ride Out

Morning Custom horseback ride through the Gros Ventre with local wrangler.
Afternoon Chef-curated picnic lunch riverside. Return for a soak in the outdoor hot tub or relax with an in-suite spa treatment.
Evening Private fireside dinner in your suite. Small-batch bourbon tasting with your group in the Alpine Lounge.

Day 3: Rodeo Under the Tetons

Morning Breakfast in-suite or on the terrace. Visit a local working ranch: learn to rope, explore the stables, or catch a horse demo.
Afternoon Leisure time for rest or shopping in downtown Jackson.
Evening VIP experience at the Jackson Hole Rodeo. Post-rodeo cocktails back at Caldera House.

Day 4: River Adventure & Open Skies

Morning Guided fly fishing drift boat trip on the Snake River.
Afternoon Light lunch and a wellness reset: massage, stretch session, or infrared sauna.
Evening Sunset dinner at Shin Shin or your choice of chef-prepared in-suite meal. Western film screening or stories by the fire.

Day 5: The Last Hurrah

Morning Final walk through the Village or sunrise yoga on your balcony.
Afternoon Packing assistance and farewell from the concierge team. Optional visit to the Jackson Hole History Museum before departure.

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Guide Notes