SKYLINE SPRING ROUNDUP
All-inclusive Glamping Experince in the Beartooth Foothills of Montana
Spring in the foothills is when everything begins to move. Horses are brought in from the open range, calves are sorted and paired, and the work that sets the tone for the entire year comes to life. The Skyline Spring Roundup Experience invites families, couples, and adventurous travelers to join our crew for a five night stay in the Beartooth foothills, where you will help prepare our herd for the summer season and experience the West in a way few ever do.
DATES
June 1st-6th, 2026
LOCATION
Beartooth Mountain Foothills
(pick-up in Billings, Montana)
PRICE
$2,800-$3,200
GROUP SIZE
10-12 Guests
RIDE, ROPE & ROUNDUP
Includes:
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5 Night All-Inclusive Glamping Experience
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All Meals: Breakfast, Lunch, & Dinner
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Horseback Riding and Horsemanship Workshops
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Wagon Rides, Horse Shoe Competitions, and Other Ranch Lifestyle Events
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Cattle Branding
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Live Music Around the Campfire
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Transportation to and from the Billings, Montana, airport
* alcoholic beverages and gratuities are not included
Shared Accommodations: $2,800 per person
Private Accommodations: $3,200 per person
Each year, our horses and cattle spend winter and spring grazing thousands of acres of private range land in the rolling hills between Red Lodge and Joliet, Montana. This is where the Skyline story quietly continues while the mountain trails rest under snow. The Skyline Spring Roundup opens that world to you. During this five-night retreat, you will ride out with the crew and cowboys, help gather and move cattle, check on the horses, and assist with the important spring work that keeps a ranch running. Along the way, you will learn how we prepare our herd for the coming season, from simple daily care to larger projects that only happen once a year. Back at camp, the comforts are anything but rough. Guests stay in glamping accommodations, enjoy elevated camp meals prepared from our historic chuckwagon, and relax around the campfire as the foothills fade into starlight. It is an immersive, family-friendly experience that blends real ranch work with time to rest, connect, and enjoy being together in a beautiful place.
About the Foothills Experiences:
For over sixty years, Skyline’s horses have spent their winters roaming the wide, rugged foothills of the Beartooth Mountains. It’s here, long before the summer trails open in Yellowstone National Park, that the work of Skyline truly begins. Horses are trained, cattle are tended, and life follows the timeless rhythm of the range. These new foothill experiences offer guests a rare behind-the-scenes look into that part of the Skyline story. They’re a chance to slow down, to learn, to connect with the land and the lifestyle that built this ranch. Whether you’re joining us for Cowgirl Cow Camp, the Skyline Spring Roundup, or Painting on the Range with Sarah Dean, you’ll find the same sense of authenticity, heart, and Western spirit that defines everything we do at Skyline Guest Ranch.
Listed below is the tentative itinerary:
DAY 2
HORSEMANSHIP & HORSEBACK RIDING
Wake to the comforting sound of sizzling bacon and the smell of fresh cowboy coffee drifting across camp. After breakfast, you’ll join our crew for a hands-on horsemanship introduction, learning the foundations of working with your horse and communicating with confidence. By afternoon, you’ll be riding through the rolling foothills, taking in sweeping views and letting the rhythm of the saddle settle into your bones. Return to camp for a hearty dinner, followed by a fun horseshoe tournament under the open Montana sky.
DAY 1
WELCOME TO COW CAMP
Your week begins in Billings, Montana, where our team will meet you at the airport or your hotel for a scenic shuttle into the Beartooth foothills. Once the pavement ends, you’ll trade vehicles for a wagon and rumble your way into Cow Camp, surrounded by sagebrush hills, grazing horses, and the quiet beauty of spring on the range. After settling into your cozy glamping accommodations, enjoy your first camp-cooked dinner and gather around the fire for stories, laughter, and live music.
DAY 3
SPRING HORSE ROUNDUP
Today offers a true taste of the Western lifestyle. Spend the day in the saddle, riding out with the cowboys and helping with real ranch work. Whether you’re gathering and moving cattle across the open range or checking on the horses, you’ll experience firsthand the grit and reward that define ranch life. After a long and satisfying day, return to camp for an elevated dinner, then settle in for live music, good stories, and peaceful moments around the campfire.
DAY 4
FULL DAY OF CATTLE WORK
Today offers a true taste of the Western lifestyle. Spend the day in the saddle, riding out with the cowboys and helping with real ranch work. Whether you’re gathering and moving cattle across the open range or checking on the horses, you’ll experience firsthand the grit and reward that define ranch life. After a long and satisfying day, return to camp for an elevated dinner, then settle in for live music, good stories, and peaceful moments around the campfire.
DAY 6
FAREWELL TO THE FOOTHILLS
Enjoy one last hearty breakfast as the sunlight spreads across the foothills and the horses graze nearby. Then it’s time to say your goodbyes, load up your gear, and hop on the wagon for the ride back toward civilization. Our shuttle will return you to Billings with a full heart, tired hands, and memories that will stay with you long after your boots are unpacked.
DAY 5
BRANDING DAY
It’s the biggest day of the week — branding day! Fuel up with a quick breakfast before heading out for one of ranching’s most important spring traditions. You’ll help gather the herd, sort pairs, push cattle into the branding pen, and work alongside the cowboys to brand the calves. It’s tough, exciting, and gives you a glimpse into the heart of Western ranch life. Wrap up this unforgettable day with a farewell dinner and live music around the campfire as you celebrate your accomplishments, new friendships, and the incredible week you’ve shared.
ELEVATED CAMPFIRE CUISINE
Meals in the foothills are a true highlight of this retreat, blending the nostalgia of old-fashioned camp cooking with an elevated Skyline twist. Using our over 100-year-old chuckwagon and a massive flattop grill, our camp chefs prepare three unforgettable meals a day, each one crafted to surprise and delight. Mornings begin with French toast sizzling on the griddle, cowboy coffee poured piping hot, and hearty sausage to fuel your day on the range. Evenings bring stunning entrées like elk tomahawk steaks, tender shishkabobs, and skillet-seared favorites served under the open sky. And no night is complete without a warm Dutch oven dessert — think apple dumplings, bubbling cobblers, and other sweet comforts that taste even better when enjoyed beside the campfire. This is camp cooking reimagined, where timeless tradition meets elevated flavor in the heart of the foothills.
FREQUENTLY ASKED QUESTIONS
Para obtener información sobre cómo reservar su propio retiro, contáctenos en:
(406) 838-2380