SKYLINE SPRING ROUNDUP
An Immersive Horsemanship Glamping Experience in the Beartooth Foothills
Spring is an exciting time for the Skyline horse herd. It is when we begin gathering the horses, working with the young ones, and preparing the entire herd for the busy summer season ahead. During the Skyline Spring Roundup, guests step behind the scenes of ranch life to experience the horsemanship, care, and teamwork that go into developing the horses that carry our guests through the mountains all summer long.
The Skyline Spring Roundup invites a small group of guests to step into this special moment of the year. During this five-night all-inclusive glamping experience, you will ride with our crew, participate in the official Skyline horse roundup, and learn the fundamentals of horsemanship while helping prepare our horses for the coming season. It is a rare behind-the-scenes look at how a working guest ranch develops and cares for the horses that carry our guests through the mountains each summer.
DATES
June 1st-6th, 2026
LOCATION
Beartooth Mountain Foothills
(pick-up in Billings, Montana)
PRICE
$2,800-$3,200
GROUP SIZE
8-10
Includes:
-
5 Night All-Inclusive Glamping Experience
-
All Meals: Breakfast, Lunch & Dinner
-
Guided Horseback Riding in the Beartooth Foothills
-
Skyline Horse Roundup Participation
-
Halter Breaking, Working with Yearlings, & Colt Starting Demonstrations
-
Farrier Demonstration and Horse Care Discussions
-
Veterinary Herd Check and Horse Health Education
-
Campfire Evenings with Live Music
-
Horsemanship & Groundwork Workshops in the evenings (optional)
-
Wagon Rides, Horse Shoe Competitions, and Other Ranch Lifestyle Events
-
Transportation to and from the Billings, Montana, airport
* alcoholic beverages and gratuities are not included
Shared Glamping Tent: $2,800 per person
Private Glamping Tent: $3,200 per person
Each year, our horses spend the 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 our crew to help gather the Skyline horse herd, take part in the official horse roundup, and learn the horsemanship that prepares these horses for the busy summer season ahead. Guests will have the opportunity to work with young horses, observe farrier work and veterinary herd checks, and see firsthand the care and training that go into developing dependable mountain horses. 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 meaningful hands-on learning with time to rest, connect, and enjoy being together in a beautiful place.
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, we ride out across the foothills to gather the Skyline horse herd from the surrounding range. This is the official spring roundup, where the horses are brought together and prepared for the summer season. Guests will ride alongside our crew, helping locate, move, and gather horses across the open country. (Riding in the actual roundup is based on experience level and current conditions!)
DAY 4
THE PERFECT MIX OF RELAXATION & HORSEMANSHIP
Start the morning with a relaxed breakfast in camp, followed by some well-earned downtime. Guests can unwind with optional yoga or a massage while enjoying the peaceful foothills surrounding camp. Later in the morning, join our crew as the veterinarian visits to conduct the herd’s Coggins testing, offering a firsthand look at the health checks required for traveling and working horses.
In the afternoon, step into the world of horsemanship as you help halter break yearlings and observe demonstrations of colt starting and groundwork techniques. The evening wraps up with a little friendly competition during a horseshoe tournament, followed by a hearty dinner and stories shared around the campfire.
DAY 5
YEARLING BRANDING, FARRIER WORK & FAREWELL RIDE
The morning begins with helping our crew freeze-brand the yearlings. Guests will observe the process up close and lend a hand where appropriate while learning about the purpose behind freeze branding. Spend time with our farrier as he trims and shoes the herd. In the afternoon, enjoy a farewell horseback ride through the rolling foothills surrounding camp before returning for a relaxed evening and closing dinner under the Montana sky and music 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.
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