To truly experience the cowboy way in Sheridan, WY, you’ll need more than just a single day. Plan for at least three days to soak in the legend and lore of local icons, outlaws, and authentic Western culture—you won’t regret it.
For the ultimate Western experience, WYO Rodeo Week is the best time to visit. But if your timing doesn’t align, you can still immerse yourself in cowboy culture with events like the Eatons Horse Drive, Don King Days, or the Sheridan WYO Winter Rodeo, where you’ll find skijoring, hot cider, and snow-capped mountain views. Ready to experience all the things cowboys do in Sheridan, WY? Saddle up for our “Three Days as a Cowboy” itinerary.
Day 1 Itinerary: A True Wild West Western Experience Near Sheridan
Your first day is packed with authentic cowboy experiences. Begin with the natural wake-up call of elk bugling, then take a road trip to the legendary Hole-in-the-Wall, a historic hideout for outlaws in the late 1800s. End your day by soaking in the beauty of a stunning Wyoming sunset.
Greeting the Day: A Morning in the Life of a Cowboy
Whether you’ve booked a stay at one of Sheridan County’s legendary ranches or mountain lodges, or you’re staying somewhere closer to town, it’s time to begin your day in the life of a cowboy.
At the Ranch or Mountain Lodge:Experience the natural wake-up call of elk bugling or roosters crowing.Spend an hour tossing a fly line into a stream, cover a bit of ground on horseback, or photograph moose, elk, deer, or dozens of beautiful migratory birds as you take in the majesty of the mountains.
Breakfast in Town: For those closer to town, enjoy a hearty cowboy breakfast at the Silver Spur Cafe, featuring the local favorite, chicken fried steak with gravy.
Wild West Afternoons: Historical Sites & Western Foods
Journey to Hole-in-the-Wall Outlaw Hideout: Travel to Johnson County (2.5 hour drive) to explore this legendary site associated with Jesse James, Butch Cassidy and the Wild Bunch Gang. The Hole-in-the-Wall is a scenic sandstone escarpment and the “hole” is a gap in the red wall that, legend has it, was used secretly by outlaws to move horses and cattle from the area.
Lunch in Story, Wyoming: On your way back, visit the hamlet of Story for lunch at the Wagon Box Inn, known for its beautiful outdoor setting and delicious “Mountain West Fare”.
Cowboy Evenings: Relaxing Ranch Moments
As the sun sets over the vast Wyoming landscape, enjoy the peaceful hues of pink and orange stretching across the sky. Relax in a cozy spot, perhaps with a local Black Tooth brew in hand, and soak in the tranquility. Reflect on the day’s adventures and start planning for the next day’s exciting experiences. It’s the perfect way to unwind before tomorrow’s journey into the heart of cowboy country.
Day 2 Itinerary: Cowboy Lifestyle & Western Adventures in Sheridan
Get ready for a day packed with authentic Western experiences and all the things cowboys do in Sheridan, WY, from horseback adventures in the Bighorns to hearty ranch-style meals. It’s the perfect way to dive deeper into cowboy culture and the rugged beauty of Wyoming.
Morning in the Old West: Breakfast at Midtown Cafe
Plan on getting your boots dirty today. Before heading out for another day of action, cowboy up for breakfast at Midtown Cafe on Main Street. Try the Huevos Rancheros or Chilaquiles, paired with a refreshing Big Horn smoothie.
Bonus Must-Visit Activity: If it’s late May, you’re in luck; the Eaton’s Horse Drive is an annual tradition when cowboys from Eaton’s Ranch drive their herd in from winter grazing areas straight through town – down 5th Street in front of the Sheridan Inn, across Main, and out toward the ranch.
Saddle Up: Afternoon Rides into the Bighorn Mountains
If you’re staying at a guest ranch, it’s time to saddle up for the pack trip of a lifetime—there’s nothing like riding into the Bighorns with the sun at your back and mountains towering above. For those not staying at a ranch, you can still experience this adventure by booking a two- to five-day pack trip with one of our local outfitters.
Cowboy Nights: Unwind at The Mint in Sheridan
Belly up to the bar at The Mint, the famed former speakeasy on Main. Tip one back and take the trophy tour, explore history through photographs, and check out the thousands of brands on the wall panels.
Day 3 Itinerary: Discovering the Western Experience in Sheridan’s Natural Beauty
Get ready to immerse yourself in the authentic western lifestyle as you explore the stunning landscapes and learn about the things cowboys do in Sheridan, WY. From outdoor adventures to downtown exploration, today is all about connecting with the cowboy spirit in the heart of Wyoming.
Breakfast in Cowboy Style: Then Off to Bighorn National Forest
Breakfast at Cowboy Cafe: Take your breakfast with a side of pie at the cozy Cowboy Cafe, the beloved local dining spot located in Historic Downtown Sheridan.
Bighorn National Forest: The morning is the perfect time for anadventure in the breathtaking Bighorn National Forest, where towering pine trees, crystal-clear streams, and rugged mountain trails await. Explore the diverse landscapes, from rolling meadows to dramatic canyons, all teeming with wildlife. Whether you’re hiking, horseback riding, or simply soaking in the serenity, the fresh mountain air and stunning views will energize you for the day ahead. It’s a perfect start to your cowboy journey in Wyoming’s wild beauty.
Bonus Must-Visit Activity: If you’re visiting in winter, join the excitement of the WYO Winter Rodeo. Test your mettle in skijoring, a sport where a horse and rider tow a skier along a snowy course.
The Cowboy Way at Midday: Exploring Sheridan’s Downtown Charms
Downtown Exploration: Post-lunch, take a leisurely stroll through downtown Sheridan. Visit King’s Saddlery to witness the art of rope making and leather crafting, and try your hand at tossing a rope in the Don King Museum.
Cowboy Competitions: A friendly little competition between cowboys has been a part of Western culture for centuries. Book an archery class at Rocky Mountain Discount Sports, and let your inner Robin Hood loose. Or start a match at the Kendrick Park horse shoe pits, the competitions there can get fierce.
Sheridan’s Evenings: Cowboy Culture Under the Stars
Live Country Music and Local Entertainment: As night falls, Sheridan transforms into a hub of cowboy culture and music. Check out the live country music performances at the WYO Theater, the Warehouse, and Luminous Brewhouse. These venues often feature local and visiting artists, providing an authentic western music experience.
Stargazing Opportunities: End your night by admiring Sheridan’s clear night skies. The town’s location away from large city lights makes it an ideal spot for stargazing, allowing you to unwind and reflect on your adventures.
