National Parks, Chuckwagon Dinners and a Famous Cowboy Bar in Jackson, Wyoming

Jackson is not only a popular basecamp for national park travelers heading to the Grand Tetons and Yellowstone, but also a charming Western town brimming with cowboy-centric activities.

The team at Snow King Resort can link travelers up with horseback riding outfitters or set up reservations for chuckwagon dinners, with horse-drawn covered wagons rattling into Cache Creek Canyon for meals under the stars.

The resort’s prime location is a short walk to Town Square, home to the legendary Million Dollar Cowboy Bar. Snag a saddle seat at this honky tonk’s bar, order a cocktail made with Wyoming Whiskey, enjoy live music, and, if you find yourself here on a Thursday night, join in on complimentary dance lessons.

Cowboycationers can also sync up visits with the summertime Jackson Hole Rodeo (the fairgrounds are down the street from Snow King Resort) or Old West Days, which are held each May and include stagecoach rides, a parade, and the auctioning off of antlers, coveted souvenirs that have been naturally shed on the National Elk Refuge.

The resort’s location at the base of Snow King Mountain also means easy access to mountain activities like the Cowboy Coaster. Riders control the mountain coaster’s speed with brakes, slowing down to take in views of the Tetons.

One more thing: Hayden’s Post, the resort’s signature restaurant, nods to the Hayden Expedition of 1871. A photographer on the expedition captured photos of the parks, which became instrumental in advocating for Yellowstone’s founding.

Ghost Towns, Wild West Museums and Horseback Riding in the Valley of the Sun

The Valley of the Sun draws travelers for spring training baseball games, bachelorette parties, golf getaways, spacations and more. But the Phoenix metro’s Wild West spirit remains palpable at nearby attractions, too, like the 90-acre outdoor Pioneer Arizona Living History Museum where tourists can watch gun show reenactments and explore frontier homes, and Goldfield Ghost Town, a resurrected boom-and-bust town with tours of the abandoned gold mine.

Cowboycation seekers can rest their hat at Rise Uptown, a stylish boutique hotel in the heart of Phoenix. Choose some tunes to play from the vinyl record library, cool down at the pool or warm up at the firepit.

Or, retreat to Litchfield Park and check in at The Wigwam Resort, where Western heritage runs deep. Originally established as The Wigwam Guest Ranch in 1929, the resort was a true desert retreat, complete with stables and a stagecoach that took guests to cowboy cookouts under the Arizona sky. While times have changed, the spirit of the West is still alive in every corner of the resort, which now boasts luxurious Southwest-inspired architecture and interiors.

Just minutes from Wigwam, guests can saddle up for horseback riding and explore the scenic desert trails with guided excursions. The hotel also hosts pop-ups throughout the year when visitors can personalize their own cowboy hats. Through a partnership with Woodford Reserve, Wigwam also features exclusive tastings from its private barrel in addition to whiskey cocktails paired with pecan wood fired steaks at Litchfield's, the resort’s signature restaurant.

In Scottsdale, set out on a morning hike in the saguaro-studded McDowell Sonoran Preserve. For a taste of the Wild West, spend an afternoon perusing Western Spirit: Scottsdale’s Museum of the West. The Abe Hays Family Spirit of the West Collection is a treasure trove of 1,400 Old West artifacts including spurs, chaps, saddles, sheriff badges and more. Rest up at Hotel Valley Ho, an iconic mid-century retreat with modern amenities in the heart of Old Town. Local expert Ace Bailey, of Ultimate Art and Cultural Tours, leads hotel tours that dive into the resort’s famed Hollywood past as well as historic Old Town tours that explore how Scottsdale became "The West's Most Western Town.”

Rodeos, Museums and Cowboy Tubs in San Antonio

Dating back to San Antonio’s early days when Spain ruled Texas and vaqueros (cowboys) rounded up cattle on Mission ranches, the Alamo City stakes its claim as the birthplace of the American cowboy.

Today’s visitors can tap into Wild West moments throughout Hill Country, including, of course, rodeos. The San Antonio Stock Show and Rodeo draws 1.3 million visitors to San Antonio every February and the Tejas Rodeo Company hosts weekly rodeos March through November.

Museum-goers can stroll through the galleries at Briscoe Western Art Museum, which is located along the San Antonio River Walk and is home to artifacts like Pancho Villa’s saddle, an authentic chuck wagon, plus art from the American West. At Buckhorn Saloon and Museum and Texas Ranger Museum check out Texas Ranger artifacts and chow down on a burger in the on-site saloon.

Spend your nights (and a good part of your days) at La Cantera Resort & Spa, a luxurious stay that’s spread out over 550 acres atop one of the highest and most beautiful points in San Antonio. The lobby-level Sire Bar pays homage to King Ranch, the largest ranch in the United States, and is stocked with a standout selection of brown spirits.

Before riding off in the sunset, enjoy some pampering with a treatment at the resort’s Loma de Lida Spa. Might we suggest a soak in a cowboy tub with a glass of champagne and views of Texas Hill Country unfolding below?

Explore these cowboycation destinations and others across the Benchmark Resorts & Hotels portfolio, a collection of more than 50 distinct, independent properties by Pyramid Global Hospitality. Located in diverse destinations across the globe, Benchmark’s resorts and hotels reimagine immersive travel, inspiring guests to create memories born from meaningful exploration, authentic moments, and innovative experiences – no matter the occasion. Benchmark guests can earn complimentary gift cards, on-property perks, and destination experiences through the collection’s signature Mosaic Rewards program.