This Underrated Northern Wyoming Town Is One of the Coziest Western Destinations in the U.S.

At the northern tip of Wyoming, practically huddled up against the border of Montana, travelers will find the underrated 20,000-person city of Sheridan. This quaint Cowboy State city is a less crowded, welcoming spot to experience the Wild West with a walkable downtown area and easy access to the Bighorn Mountains. In the winter, it’s known as home to the annual Sheridan Winter Rodeo (think Skijoring galore) but hosts an abundance of outdoor activities every season. 

Start the day with a morning brew or bite on Main Street at the veteran-owned, cozy-but-no-frills Bison Union Coffee Company. A few minutes drive outside of downtown, visit community favorite steakhouse McGregor’s, known for its large patio boasting stunning views of the Bighorn Mountains. 

Sheridan also features a collection of local breweries. Smith Alley Brewing Company serves top-notch craft beer and tasty bites in a cool, industrial-feeling space. Across town, Black Tooth Brewing Company (named after the nearby 13,014-foot Black Tooth Mountain) feels like a bustling hometown spot to hang out with an award-winning beer. 

For a unique thrill, daredevils and aerospace enthusiasts can visit the Sheridan County Airport to embark on a scenic flight over the Bighorn mountains — or even take personal flight lessons with Sheridan Pilots 307 Flight School.  

Those who prefer to stay on the ground can embark on a self-guided walking tour of Historic Downtown Sheridan. Sheridan’s self-proclaimed motto says, “What’s old is always new,” meaning the city carefully preserved these buildings to showcase their original facade while transforming them into a modern collection of shops and restaurants. Admire the dozens of landmark buildings downtown on the National Register of Historic Places, like the local performing arts center — WYO Theater. 

To become immersed in the culture and history of the region, stop at the Brinton Museum. This cost-free working ranch site sits directly at the foothills of the Bighorn Mountains. The museum showcases a range of beautiful 19th, 20th, and 21st-century Western and Indigenous art, including exhibits like a collection of beaded Native American robes and a lineup of cultural photography.

Outdoor enthusiasts can drive out to the nearby Bighorn National Forest, known as the sibling mountains of the Rockies. Ski at the uncrowded ​​Antelope Butte Recreation Area, which is tucked into the mountains and features enough runs to keep any skier busy for hours. These peaks also boast seemingly endless snowshoeing, mountain biking, and camping in the warmer months.    

On the way back into downtown Sheridan, stop at the picturesque village of Dayton to grab a hot chocolate and a souvenir at the warm and welcoming Dayton Mercantile. This longstanding family-owned shop bursts with charm and sells a variety of antiques, trinkets, and snacks. 

Spend the evening at the iconic Sheridan Inn snuggled up at the lobby’s crackling fireplace. This landmark property dates back to the late 1800s and is perched across the street from the historic railroad station. Legendary American soldier William F. “Buffalo Bill” Cody lived here from 1894 to 1902 and was said to have used the hotel’s front lawn to hold auditions for his "Wild West" show. Each of the 22 rooms at the inn is themed with the key characters from Buffalo Bill’s life and features artifacts depicting the histories of these people in their furnishings. 

Whether exploring the town and browsing local shops or setting out on a cowboy adventure — a trip to Sheridan feels like a journey back in time to the dauntless days of the Wild West.