COW CAMP N' CANVAS
A Plein Air Painting Adventure with Sarah Dean
This spring, join artist Sarah Dean in the rolling foothills of the Beartooth Mountains of Montana for a one-of-a-kind creative retreat that blends the beauty of Western landscapes with the rhythm of ranch life. Guests will enjoy a luxury glamping adventure, enjoy gourmet camp-style meals, and spend each day painting from life in a spacious white wall tent surrounded by sweeping views and grazing horses and cows. Between painting sessions, guests can ride out through the foothills, watch the cowhands at work, and soak in the beauty that fuels so much of Western art.
DATES
May 25th-30th, 2026
LOCATION
Foothills of the Beartooth Mountains
(pick-up in Billings, Montana)
PRICE
$3,600-$4,000
GROUP SIZE
10 Artists
Includes:
-
5 Night All-Inclusive Glamping Experience - Private or Shared Accommodations
-
All Meals: Breakfast, Lunch, & Dinner
-
Horseback Riding in the Beartooth Mountain Foothills
-
Four Days of Painting Instruction, Group Outings, & Activities
-
Outdoor Morning Yoga Session
-
Wagon Rides, Horse Shoe Competitions, and Other Ranch Lifestyle Events
-
Live Music Around the Campfire
-
Easels, Solvents, and Some Basic Supplies (Supply list will be emailed after registration).
-
Transportation to and from the Billings, Montana, airport
* painting supplies, alcoholic beverages, and gratuities are not included
Shared Accommodations: $3,600 per person
Private Accommodations: $4,000 per person
Non-Artist Partners & Friends: $1,200 per person
Join Sarah for an immersive workshop set in the rolling foothills of the Beartooth Mountains, where she will guide you through her process of capturing the spirit and movement of horses on canvas. You’ll begin with plein air sketches among the sagebrush and open range, sharpening your drawing skills as horses and cattle graze nearby. From there, you’ll move into the white-wall painting tent to begin work on your canvas. Using the Alla Prima method, Sarah’s instruction focuses on painting horses expressively, using detail sparingly and with intention so each brushstroke feels alive. Throughout the retreat, you’ll have the opportunity to watch Sarah demo an original painting, followed by personalized one-on-one guidance tailored to your artistic goals. Learn how to choose the perfect reference photo, master color mixing, and avoid overworking the paint so your finished piece remains dynamic, fresh, and full of Western energy.
Before you arrive, all attending artists will receive a detailed workshop supply list and a call with Sarah to help you prepare. You’ll also select a reference photo featuring one of Skyline’s own free-roaming horses — the perfect muse for a week of painting on the open range.
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 1
WELCOME TO THE FOOTHILLS
Arrive in Billings, Montana, where our team will greet you at the airport or your hotel for a complimentary shuttle into the rolling Beartooth foothills. Once the pavement ends, trade your car for a wagon and enjoy a scenic ride into camp, taking in the sagebrush hills, roaming horses, and wide-open spring skies. Settle into your glamping accommodations, savor your first camp-cooked meal, and end the evening gathered around the fire swapping stories as the stars come out.
DAY 2
RIDE INTO INSPIRATION
Wake to the smell of breakfast and cowboy coffee before joining us for a relaxed workshop orientation. From there, head out on horseback through the foothills, riding among free-roaming horses and cattle that bring the West to life. Let the landscape spark your creativity as you prepare for the days of painting ahead. As the sun sets, enjoy live music around the campfire and soak in the magic of spring evenings on the range.
.jpg)
DAY 3
SKETCH, STRETCH, AND SETTLE IN
Begin your morning with an outdoor yoga session to warm up and reset your mind before gathering for a hearty chuckwagon brunch. Then step into the painting tent and start laying the foundation for your artwork. Spend the day sketching compositions, sealing canvases, and preparing for paint. The evening concludes with an elevated camp dinner served beneath the big Montana sky.
DAY 4
PAINT THE WESTERN STORY
Dive into a full day of painting instruction as Sarah Dean guides you through bringing depth, color, and emotion to your canvas. Surrounded by foothills, horses, and the constant hum of ranch life, inspiration comes easy. Finish class just in time for a peaceful evening wagon ride through the sagebrush, followed by dinner and a friendly horseshoe tournament back at camp.
DAY 5
FINAL STROKES & FAREWELL RIDE
After breakfast, return to your canvas to add final touches, highlights, and finishing strokes until your painting tells its full Western story. With your artwork complete, climb back into the saddle for one more ride through the rolling foothills, snowcapped peaks rising in the distance. The day ends with a special farewell dinner to celebrate your unforgettable week of creativity and connection.
DAY 6
ONE LAST MORNING ON THE RANGE
Savor one last breakfast in camp before a wagon ride back toward the trailhead. From there, enjoy a relaxing shuttle to Billings, Montana, carrying home your finished painting, new friendships, and a week’s worth of inspiration.
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.
SARAH DEAN
Equine & Western Lifestyle Painter
Born and raised in Colorado, Sarah Dean discovered her love for drawing at an early age, sketching everything from horses to the sweeping landscapes that surrounded her. Deeply influenced by the Western way of life, she developed a passion for capturing the essence of the horse—whether it’s a seasoned cowpony working cattle under the vast sky or a wild mustang running free across the open range.
Over the years, Sarah refined her skills through dedicated training under professional artists, immersing herself in the disciplines of oil painting and graphite drawing. With each stroke of her brush or pencil, she strives to bring life to her subjects, preserving fleeting moments of strength, grace, and untamed spirit. Her work invites viewers to not only observe but experience the stories within each piece. Through her art, Sarah seeks to bridge the past and present, celebrating the timeless beauty of the West while stirring the imagination of those who share her love for its enduring traditions.
