SADDLE UP & PAINT WITH SARAH DEAN
An Immersive Oil Painting Retreat at Skyline Guest Ranch
Join us for an exclusive workshop blending artistry and adventure, hosted by Skyline Guest Ranch with instruction by equine artist Sarah Dean. Nestled in the breathtaking mountains of Montana, this unique retreat invites you to step away from the everyday and into a world where creativity and the great outdoors collide. Spend your days painting under Sarah’s expert guidance, while also embracing the spirit of the West through horseback riding, hiking, chuckwagon dinners, campfires, and much more. Whether you’re an experienced artist or just beginning your creative journey, this workshop is designed to ignite your imagination, sharpen your skills, and immerse you in the beauty, movement, and essence of the horse—all while soaking in the magic of Skyline’s high-country haven.
WHERE THE TRAIL LEADS TO INSPIRATION
Dates: August 25th-30th, 2025
Location: Skyline Guest Ranch, Cooke City, MT
Pricing: Pricing ranges from $2,700 to $3,700 depending on accommodation type. Non-artist spouses, partners, and friends can join the fun for $1,500. Premium accommodations include our Colter Room, Bunkhouse Cabin, and Glamping Tent.
Shared Accommodations: $2,700 per person
Private Standard Accommodations: $3,500 per person
Private Premium Accommodations: $3,700 per person
Non-artist Spouses, Partners, & Friends: $1,500 per person
Includes:
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5 Nights - Private or Shared Accommodations at Skyline Guest Ranch, Cooke City, Montana
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All Meals: Breakfast, Lunch, & Dinner
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Full-Day Horseback Ride in Yellowstone National Park
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Four Days of Painting Instruction, Group Outings, & Activities
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Outdoor Morning Yoga Session
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Chuckwagon Dinner & Wagon Rides
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Easels, solvents, and some basic supplies (Supply list will be emailed after registration).
* most painting supplies, alcoholic beverages, and airport transportation are not included
Join Sarah for an immersive workshop where she will guide you through her process of capturing the majestic beauty of horses on canvas. You’ll start with plein air sketches to sharpen up your drawing skills, and then you’ll move indoors to the beautiful Moose Ridge Cabin to begin work on your painting. Using the Alla Prima method, Sarah’s instruction will center around learning to paint horses expressively, using detail sparingly and with purpose. You’ll have the chance to watch Sarah demo an original painting, as well as receive personal instruction tailored to your own skills as you create a painting of your own. Learn how to choose the perfect reference photo, master color matching, and avoid overworking the paint, ensuring that your finished piece feels dynamic and fresh.
All attending artists will receive a detailed workshop supply list and a call with Sarah before the trip to make sure that you feel confident and ready to paint! You’ll get to choose your reference photo featuring one of the ranch’s own horses, thanks to the beautiful photography of Amanda Tonagel Photography.
Listed below is the tentative itinerary:
Day 1
Check-In & Welcome Dinner
Guests check in at Skyline (3-6 pm) and get settled into their accommodations. Gather together for a ‘kickoff’ meeting followed by a welcome dinner. Settle in and get to know each other with Dutch oven desserts around the campfire.
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Day 2
Horseback Ride in Yellowstone
After breakfast, set out into Yellowstone National Park for a Horseback Ride into the backcountry. Get inspired by your surroundings and be sure to bring along a sketch pad and paper to document your inspiration and get loosened up and ready to paint. In the late afternoon head back to the ranch for a short instructional session followed by dinner.
Day 3
Painting in Paradise
Wake to an outdoor yoga session to get blood circulating followed by an outdoor chuckwagon brunch. Then off to painting! Spend the morning session sketching out your canvas, sealing, and preparing the canvas for paint. Break up painting with a short afternoon waterfall hike before mixing your palettes. End the day with an amazing elevated homemade dinner.
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Day 4
Settle in & Paint
Settle in for a full day of painting instruction. Enjoy a picnic lunch on the Skyline property and get some fresh air before returning to the studio. Conclude instruction in time for a Chuck Wagon Dinner, wagon rides, and music around the campfire.
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Day 5
Finishing Touches
After breakfast, participants will break into smaller groups to take a trail ride in the Beartooth Mountains. Times will be staggered to allow for more personalized one-on-one instruction. Paint through the afternoon and conclude the workshop in time for a farewell dinner.
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Day 6
Check-Out
Enjoy one last meal as a group together before saying your goodbyes. Guests will check out (10am) leaving with newfound knowledge, unforgettable experiences, and memories that will last a lifetime!
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.
All Riding Levels Welcome: At Skyline Guest Ranch, we believe that the joy of horseback riding should be accessible to all. Regardless of your riding experience or ability level, you are warmly welcomed to join our our experiences. Our knowledgeable guides are not only skilled equestrians but also adept at tailoring the riding experiences to accommodate your individual comfort level. Whether you're a seasoned rider seeking an exhilarating adventure or a novice looking to explore the beauty of the Old West on horseback, our team is dedicated to ensuring that your time with us is enjoyable, safe, and unforgettable. We do not have a set weight limit for riding horses, but you do have to be able to mount your horse unassisted from level ground without the use of a mounting block.
Travel Information
Traveling to our beautiful ranch is an adventure in itself, offering stunning views of Yellowstone National Park and the majestic Beartooth Mountains along some of the most scenic and iconic roads in America. Please note that transportation is not included in the retreat package. However, we are happy to assist you in organizing and setting up transportation to the ranch, offering a range of options to suit various budgets and preferences.
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Car Transfer
Car transfers are available for those flying into Bozeman, MT; Billings, MT; or Cody, WY. Prices vary depending on the airport and typically range from $500 to $800 per direction. We can assist in arranging shared transfers with other guests traveling to the ranch. Private and group transfers are available. For a mixed experience, you can also choose to take a helicopter to the ranch and return to the airport by car shuttle. -
Car Rental
Renting a car for the week is our most popular option, offering flexibility and convenience. Prices vary depending on the rental company and vehicle type. Having your own car allows for seamless transportation into Yellowstone for day trip excursions and gives participants the freedom to explore the area during itinerary downtimes. We recommend that participants rent cars and drive to the ranch from one of the following three airports:-
Cody, Wyoming (1.5 Hours)
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Billings, Montana (3 Hours)
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Bozeman, Montana (3.5 Hours)
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Helicopter Transfer
Experience the breathtaking beauty of Yellowstone National Park from above with a helicopter transfer. This luxurious option takes you directly from Bozeman Airport to the ranch. The cost is approximately $1,000 per person, per direction. It’s a splurge, but an unforgettable adventure!
Feel free to contact us for assistance in arranging your preferred mode of transportation. We’re here to ensure your trip is as smooth as possible!
LUXURY ACCOMMODATIONS
Skyline prides themselves in offering beautifully designed lodging options inside our main lodge, premium bunkhouse cabin, and our glamping tent. Whichever option you choose, we invite you to immerse yourself in the lap of luxury amidst the breathtaking landscapes of the Beartooth Mountains of Montana!
ELEVATED HOME COOKING
At Skyline Guest Ranch, we elevate home cooking to an unforgettable experience, serving gourmet dishes like filet mignon, elk tomahawks with red wine reduction, and mountain trout. Our desserts are just as memorable, from raspberry lemon cheesecake and peach pie to decadent chocolate creations. And to make every day a little sweeter, we bake fresh cookies daily, adding a cozy, homemade touch to your stay.
