Explore Sheridan

3 Day Trip Ideas in Sheridan

Welcome to Sheridan, Wyoming, your home for the next three days. Here you will find a thriving, historic downtown district, with western allure, hospitality and good graces to spare; a vibrant art scene; a robust festival and events calendar; and living history on every corner. 

Plan Your Weekend Trip Itinerary in Sheridan, WY

Whether you’re exploring historic Main Street or immersing yourself in the wild landscapes, your weekend in Sheridan unfolds with the promise of new discoveries and unforgettable moments.

Day 1: Exploring Downtown Sheridan and Local Culture

Downtown Sheridan Wyoming

Historic Downtown is a charming blend of preserved architectural treasures and vibrant modern flair. Stroll along Main Street, where 19th-century buildings house boutiques, galleries, and cozy cafes and living history around every corner.

Start Your Morning: Historic Breakfast Spots and Walking Tours

Start your day with a hearty, home-style breakfast at the historic PO News and Flagstaff Cafe, a Main Street icon for over a century, or opt for a quick bite at Glazed ‘N Confused. Energized and ready, immerse yourself in the community spirit with Sheridan’s self-guided Historic Walking Tour, offering maps at key locations like Sheridan Travel & Tourism, the Chamber of Commerce, and the Downtown Sheridan Association, or accessible online. This tour provides a fascinating glimpse into over a century of downtown history and development, with the highlight being Sheridan’s impressive collection of 50-plus master-crafted sculptures scattered throughout the community.

Afternoon Exploration: Unique Shopping and Local Art in Sheridan

Indulge in a sandwich and smoothie at Midtown Cafe on Main St., or savor authentic flavors at the El Rodeo Mexican foodtruck on Coffeen Ave. Explore Sheridan’s vibrant community calendar to discover the exciting events and activities happening during your stay. Dive into local shopping, where Sheridan’s eclectic array of shops, galleries, and boutiques await – from the western charm of Wyld ‘n Pretty to the artistic showcase at SAGE Community Arts, the unique finds at Crazy Woman Trading Co., and the treasure trove of tack and apparel at King’s Ropes and Saddlery. Whether you’re in search of one-of-a-kind jewelry, home decor, or Western clothing, Sheridan offers a delightful shopping experience for every taste. Explore the full shopping guide for a comprehensive list of local gems.

Evening in Sheridan: Top Dining and Nightlife Destinations

Stroll through Sheridan’s enchanting historic residential districts, where stately Victorian and craftsman homes stand amid towering cottonwood trees, leading you to Kendrick Park—a serene green space at the heart of the city. Revel in the abundance of public art, a bison and elk paddock, an ice cream shop, playgrounds, horseshoe pits, and covered picnic areas.

Savor the culinary delights of Sheridan at fine restaurants like the Warehouse, Las Delicias, Open Range, Wyoming Rib & Chop House, Pony Bar & Grill, Cowboy Café, and more in the downtown area. Alternatively, explore scattered gems like Sapporo Japanese Steakhouse and Golden China. Find a comprehensive list of dining options in our dining guide.

Cap off your evening with a nightcap at the legendary Mint Bar (don’t forget to capture the neon sign), or explore Wyoming’s largest craft brewery, Black Tooth Brewing Co., Luminous Brewhouse, or the Koltiska Distillery. Experience the unique historical charm of Sheridan’s watering holes, with the Downtown Craft Walking Tour map available throughout town.

Day 2: A Journey Through Sheridan’s Rich History

Trail End State Historic Site

The historic heart of Sheridan pulses with tales of cowboys, Native Americans, battles, ranching legends, and Western outlaws.

Morning: The Battle of Little Bighorn and Surrounding Historic Sites

Venture less than an hour away, just across the Montana border, to explore the profound history at Little Bighorn National Monument. For a comprehensive experience of this pivotal battle in the nation’s history, contemplate booking a custom tour with a local outfitter. Contact Sheridan Travel & Tourism at (307) 673-7120 for personalized recommendations. These tours often feature key regional highlights, including Fort Phil Kearney, the Wagon Box Fight, the Connor Battlefield, and more.

Afternoon: The Brinton Museum and Trail End Historic Site

The Brinton Ranch house, originally built in 1892, was expanded in 1927-28 to accommodate the Brinton’s extensive collections of Indian artifacts, art, historic documents, books and over 600 oils, watercolors and sketches by American artists including: Audobon, Borein, Gollings, Kleiber, Remington and Russell, to name a few.

The Trail End State Historic Site is a historic Flemish-revival style home built and inhabited by Wyoming governor and U.S. Senator John B. Kendrick. Kendrick was a successful cattleman when he commissioned the house, and he was only beginning his political career; once he became governor in 1914 and a senator three years later, Trail End became his summer home. The house is typical of homes built by prosperous Wyoming cattlemen in the early 20th century. The house was added to the National Register of Historic Places on February 26, 1970.

Evening: Step Back in Time at the Sheridan Inn and Veterans Hospital

Built in 1892 and conceptualized by William F. “Buffalo Bill” Cody, the Sheridan Inn stands as one of the city’s earliest hotels. With Cody at the helm, the hotel witnessed auditions for his touring company show from the front porch. Undergoing various restorations and renovations, the Inn now harmoniously combines 19th-century charm with 21st-century luxury, welcoming guests for overnight stays, banquet events, weddings, and tours. Each of the twenty-two rooms has been carefully revitalized to honor not only “Buffalo Bill” but also twenty-one other influential figures in his life.

Located on the historic Fort Mackenzie site, Sheridan’s Veterans Hospital traces its roots back to 1899 when Congress allocated funds for a permanent garrison. The 18th Infantry and Buffalo Soldiers of the Tenth Cavalry, returning from conflicts in Cuba and the Philippines, found respite here for recuperation and retraining. The red brick buildings, constructed in 1902, still stand, and the campus is open for daylight tours, with the privacy of patients, residents, and staff to be respected. Please note that all buildings are closed to the public except for official business.

Day 3: Outdoor Adventures in the Majestic Bighorn Mountains

Bighorn Mountains

The Bighorn Mountains have been at the center of the essential Sheridan experience for generations. The mountains boast secluded canyons, miles of hiking, biking and riding trails, secret fishing holes, epic climbing lines, and so much more. Whether exploring the scenic trails, setting up camp under the vast Wyoming sky, or capturing the essence of nature’s beauty, the Bighorn Mountains offer an unforgettable playground for those seeking an immersive outdoor experience.

Morning in the Mountains: Gear Up for Adventure in the Bighorns

Gear up for your outdoor escapade by renting a bike, acquiring backpacking or climbing essentials, or snagging other outdoor gear from top-notch outfitters like Sheridan Bicycle Company, The Sport Stop, Rocky Mountain Discount Sports, and the Fly Shop of the Bighorns. Fuel your adventure-packed day with a delightful breakfast at the Shabby Shack, where local favorites like peaches and cream French toast await, or opt for the cozy ambiance of Hygge Hearth. Head out on Highway 14 towards Dayton, the gateway to the Tongue River Canyon, offering a multi-purpose adventure trail, serene swimming and fishing spots, and some of the most breathtaking views in Wyoming.

Afternoon Thrills: Hiking Trails, Waterfalls, and Stunning Vistas

Continuing along Highway 14, ascending into the mountains, you’ll encounter Steamboat Point, an iconic outdoor symbol in Sheridan County. If you find yourself in Sheridan late in spring, the vibrant wildflowers at Steamboat create a breathtaking spectacle. Despite the short, strenuous hike to the top—less than a mile but climbing nearly 600 feet—the reward is immense, offering sweeping panoramic views of the valley below.

For those craving more outdoor adventure, follow Highway 14 to Burgess Junction, then take Highway 14A to the trailhead for Porcupine Falls. Nestled among the Bighorn Mountains, this hidden gem unveils a cascade of water pouring from a granite wall, tumbling hundreds of feet to a serene pool below.

Evening: Discover the Ancient Medicine Wheel and Reflect on Your Journey

Perched at an elevation of over 9,600 feet in the Bighorn Mountains, the Medicine Wheel is a sacred Native American site, recognized as a national historic landmark. This ancient wheel, a circular arrangement of stones, holds spiritual significance for various indigenous tribes, serving as a place of ceremony and reflection for over 7,000 years. Visitors can marvel at the breathtaking mountain scenery while experiencing the profound cultural and historical resonance of this remarkable site.

Wrapping Up Your Sheridan Day Trip Itinerary

When you finally return to Sheridan, bursting at the seams with a hundred years’ worth of frontier history, outdoor grit and local insight, you’ll be in a fine position to share Wyoming’s tall tales, historic gossip and spectacular stories with your friends and family.

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