? In 1883, Jerome Wheeler, then a co-owner of Macy's, came to the booming silver mining town of Aspen on vacation. He quickly controlled both a smelting operation and the largest mine in town, Smuggler Mine, and eventually left Macy's for Aspen. He built the Wheeler Opera House in his name, and then, wanting a grand hotel on par with those of London and Paris, loaned a local innkeeper the equivalent of $1.53 million to build the Hotel Jerome. Despite several cost overruns and the original builders skipping town before it was finished, the Jerome eventually became one of the grandest buldings in the West, and held a commanding presence in downtown Aspen. It was one of the first buildings West of the Mississippi to have fully electric lighting, along with other novelties like steam heat, indoor plumbing, and an elevator. Despite hosting mostly Wheeler's rich friends from back East to begin with, it also became integral to Aspen life since it had the only public bathroom in town.
After surviving as the only hotel in town through the downturn following Aspen's silver days, the Jerome became a regional focal point once ski lifts starting being built up Ajax Mountain, and the first celebrities to town – Gary Cooper, Lana Turner, and John Wayne among others – stayed there. Its legendary J Bar inspired a signature Prohibition-era cocktail along with an Eagles bandmember's song, and served as Hunter S. Thompson's de facto office since it had the best TV reception before cable came around. The Jerome's classic ballroom would later host Thompson's memorial service after he committed suicide on his nearby Woody Creek ranch.
? Similar to the Jerome, the New Sheridan Hotel was built on Main Street in Telluride in 1891 during the height of the town's gold and silver boom. Built first out of wood and then again in brick after burning down three years after opening, the New Sheridan is a classic Victorian that has been an outsize presence in Telluride's social life despite its modest size. The hotel bar is the oldest in town, and apparently didn't even close during Prohibition. Butch Cassidy first came to town to sow his oats in the wild and corrupt canyon of outlaws in 1884, and would return three years later to commit his first bank robbery, stealing $20,500 from the San Miguel Valley Bank next door to the New Sheridan.
? The Truckee Hotel, built in 1873 in downtown Truckee 15 minutes from Lake Tahoe, has been at the center of East-West migration for over 150 years. Situated only a few miles from where the Donner Party camped out during their tragic and cannibalistic 1846 winter while trying to take a shortcut over the Sierras, the Truckee Hotel was first the American House and hosted stagecoach drivers passing over the mountains from Nevada to Sacramento on the Dutch Flat Wagon Road. The hotel is steps from where the Intercontinental Railroad first reached town in April of 1868, and where Amtrak and freight trains still cross the Sierras today (along with I-80). The hotel itself, like many Old West Victorians, burned to the ground in 1900, and since being rebuilt, has been renamed the Truckee Hotel and is now a quaint B&B.
? The Cal-Neva Resort, straddling the border between California and Nevada on Lake Tahoe's northwest shore, has the most colorful and sordid history of any hotel on this list. Built in 1926, Judy Garland was discovered by an MGM talent agent here in 1935 when she performed with her sisters. Two years later, the hotel burned to the ground under dubious circumstances and destroyed the walls covered in stuffed wild animals and the indoor brook that hosted rainbow trout served at the restaurant. It was then rebuilt from start to finish in 40 days, after which point it was the largest casino in the country, and its first legal one as well.
In 1960, Frank Sinatra bought Cal-Neva along with a few friends from his Rat Pack. He quickly installed the Celebrity Room, a helicopter pad on the roof, and a series of tunnels so that he could move around the property with his mob friends without being seen by Hoover's FBI agents, who were often peering down from hiding spots in the hills above. Sinatra often had celebrity friends to the resort, including Sammy Davis Jr., Marilyn Monroe, and the Kennedys, which later fueled rumors that Marilyn had overdosed in one of Cal-Neva's cabins and that a few of the Kennedy brothers had had a sex party with tons of prostitutes after the casino's opening night party. After the feds spotted Sinatra's secret business partner – renowned Chicago mafia boss Sam Giancana – at the hotel with the singer, he lost his gambling license, and was forced to divest from the hotel entirely.
When developer Chuck Bluth bought Cal-Neva in 1985 after it has been closed and vacant for three years, he decided the wild history of the hotel would play a more central part of his marketing efforts, and has since offered tours of the former secret passageways and brings in Rat Pack tribute bands to play.