The rambler's guide to Cheyenne

Hundreds of thousands of cowboys and rodeo fans from all around the globe descend upon Cheyenne, Wyoming every summer for the city’s annual Frontier Days celebrations (July 18-27). Now in its 118th year, the largest outdoor rodeo in the world—known as “The Daddy of ‘Em All”—features roughly 1,500 contestants vying for $1 million in cash and prizes. But there’s much more than a rough-and-tumble rodeo to keep admirers of the Old West entertained in the Magic City of the Plains.

Day 1:

9 a.m. – In the late 1800s, the Union Pacific Railroad arrived in Cheyenne, bringing with it a rowdy bunch of railroad gangs, pioneering men and women looking for homesteads, and soldiers from the Indian frontier. Every other downtown establishment was a saloon. Brothels were tucked above every “variety” theater. Notable outlaws like Butch Cassidy were familiar figures in town and every barkeep had a running tab for Wild Bill Hicock. The outlaws and brothels might be gone now, but Cheyenne still features the same frontier spirit that captivated the area’s first settlers. Kick off a weekend in Cheyenne by getting acquainted with its storied past on a self-guided walking tour of downtown’s main plaza and historic district. Admire 19th-century cattle baron mansions in the Rainsford District, take a photo in front of the Capitol building or stroll through Holiday Park, complete with botanical gardens and a “Big Boy” steam engine. In the summer, the city offers daily trolley tours of downtown’s main attractions, letting riders hop off at any desired location.

11 a.m. – Get outfitted with a western wardrobe, starting with a custom-fit cowboy hat at The Wrangler, Cheyenne’s historic ranchwear retailer (est. 1892). Choose from more than 500 styles and shapes before letting their experts steam-fit your final selection. For the whole look, snap up a pair of new boots at the adjoining Boot Barn.

Lunch – Downtown’s Union Pacific Train Depot (est. 1886), catty-cornered from The Wrangler, isn’t just another impressive historical structure. It’s home to Shadows Pub and Grill, a homestyle eatery that offers nearly a dozen local microbrews on tap. The menu is surprisingly extensive for a pub-style café, but their burgers and BBQ don’t disappoint. Try a Hobo hefeweizen with one of their stone-baked pizzas or a Buffalo Brown Ale with a signature order of beer-battered cod.

3 p.m. – They say cowgirls have more fun in Cheyenne—and if the history books account for anything, the cliché holds more than a kernel of truth. Stop by the Cowgirls Museum & Emporium whose historical cowgirl archives and images can ignite the Wild West spirit – even in a city slicker. Learn about the women who helped create Cheyenne’s western legacy before browsing the equine-inspired accessories and memorabilia at the boutique next door. 

7 p.m. – Wyoming’s grass-fed beef and Rocky Mountain oysters are as plentiful as the plains, but if there’s one thing a cowboy can respect (other than red meat), it’s a pleasant surprise. Morris House Bistro serves up authentic lowcountry cuisine amidst the city’s sea of Western fare, inspired by Chef Dameione Cameron’s South Carolina heritage. Try succulent spins on Southern classics, like his latest creation, “Mama Lee’s fried chicken livers”- marinated, fried, and topped with a sweet Sriracha and sage aioli - that Cameron calls “Southern popcorn.” Reservations are required at the highly desirable bungalow-style restaurant, housed in the historic Esther Hobart Morris home on Carey Avenue. 

Evening – Check in at the Historic Plains Hotel (est. 1911), Cheyenne’s oldest and most elegant hotel, which has hosted celebrities and dignitaries, including the Kennedys and Roosevelts. Rooms are modern and comfortable, but the décor, like authentic Molesworth furniture and Western motif stained glass windows, root guests in the hotel’s storied past.  

Day 2:

8 a.m. – Pack a picnic lunch and head into the “wild west” backdrop of Cheyenne’s surrounding landscape. The Vedauwoo Recreation Area, known to the Arapaho as “lands of earthborn spirit,” is part of the Medicine Bow National Forest—just one of a handful of natural reserves in the area. Hike amidst the park’s staggering granite rock formations (popular with mountain climbers and bouldering enthusiasts) to find quiet places of repose. 

Lunch – Enjoy a hard-earned feast back in town at the Plains Hotel’s Capitol Grille. The hotel’s first floor café serves fresh, local cuisine in the form of hearty classics, like country fried steak and a “hay stack,” a tower of homemade fried onion straws served with a cajun remoulade.

2 p.m. – It’s easy to see a bucking bronco or bull at Cheyenne’s Frontier Days arena, but a buffalo can be a much taller order. Thankfully, the Terry Bison Ranch provides an opportunity to witness a Wyoming herd up-close during daily ranch tours. The bison are spectacular to see, but the experience comes with the whole kit and caboodle of an exotic game ranch, with a mix of ostriches, camels and miniature horses on view for the family tourism crowd.

5 p.m. – Freedom’s Edge Brewery Co. reopened in a new location downtown this year, but visitors can still expect the same standard of unique seasonal drafts (all brewed on-site), like the Udder Delight, a malty American milk stout and their refreshing Prime Meridian Pale Ale. It’s a great example of Wyoming’s growing craft brew scene, highlighted during the 19th annual Wyoming Brewers Festival (June), when a growing number of brewers showcase nearly 150 brews from Wyoming and beyond. 

Evening – Walk home to the nearby Warren Nagel Mansion B&B, a cozy 1888 Victorian B&B listed on the National Registry of Historic Places with quite the diverse guest list - from Theodore Roosevelt to Alice Cooper. Reserve the third floor’s “tower room” for the best views in the city.

Day 3:

10 a.m. –  Roll out of bed in time for the B&B’s morning breakfast—which is almost as decadent as their English high tea (served on Fridays and Saturdays). 

Noon –  Make a quick drive into the countryside for a customized trail ride (1-3 hours) “on the range” at the Bit-O-Wyo dude ranch. Or explore the undulating landscape of high ridges and shady Aspen groves on foot at the Curt Gowdy State Park. It’s a favorite destination for mountain bikers, but with scores of hiking trails and three natural reservoirs, it’s easy to make your own mark. Seek out “Hidden Falls” for a midday dip in a riparian oasis amidst labyrinthine granite formations. 

4 p.m. – Indulge in an early happy hour back in town at Suite Bistro, a chic martini and tapas bar that provides a nice change of pace from draft beer and PBR tallboys. But cowboy hole-in-the-walls are still the best bet for a wild night out in the Magic City of the Plains. Head to The Bunkhouse Bar & Grill (a highwayside dive with hitching posts for horses) to enjoy live music in the form of local country bands covering hits by the likes of Hank Williams and David Allen Coe.

Evening – Follow the cowboy hat-wearing masses to the Frontier Days Park for a corndog and funnel cake picnic at the sprawling Midway carnival. Browse the shops at Wild Horse Gulch and Indian Village before heading inside the adjacent arena for the bull riding grand championship.

What to know when you go:

American Airlines just launched nonstop flights from Dallas/Fort Worth this month.

Great Lakes Airlines also offers connecting flights to Cheyenne’s small regional airport, but more commercial flight options arrive in Denver International Airport, approximately 45 minutes from downtown Cheyenne.