Aspen Uncovered: Tales of Wealth, Wildness and Rebellion

Aspen is more than just a luxury ski destination. It’s a town where the mountains are steep, the parties are legendary, and the truth is often stranger than fiction. On this walking tour, you’ll discover the rebellious spirit and untold stories behind Aspen’s glittering facade, from counterculture movements to celebrity hideaways, and the wild characters who shaped this mountain enclave.

This 60-minute tour starts at the historic Old Armory, once Aspen’s City Hall. You’ll explore the former headquarters of Hunter S. Thompson’s outrageous campaign for sheriff, where the father of gonzo journalism hoped to disarm police and rename Aspen “Fat City” to deter investors. From there, you’ll weave downtown, past designer boutiques housed in Victorian-era buildings, and along peaceful trails with natural beauty that’s drawn both celebrities and free spirits for decades.

Along the way, you’ll discover how Aspen transformed from a rough silver mining town to an exclusive playground for the world’s elite, while somehow maintaining its rebellious soul. The tour ends at the peaceful John Denver Sanctuary, across the Ron Krajian Bridge and tucked along the banks of the Roaring Fork River, where the beloved singer-songwriter found inspiration for his most iconic songs.

During this tour, you’ll have a chance to:

• Visit the site where Hunter S. Thompson launched his “Freak Power” political movement that terrified Aspen’s establishment
• Discover the Aspen Art Museum, a striking modern structure that sparked heated debate about the town’s changing identity
• Pass by The Little Nell, the unofficial clubhouse of the rich and famous, where celebrities slip in unnoticed
• Explore Gondola Plaza, where the Silver Queen Gondola carries passengers 3,267 vertical feet up Aspen Mountain
• Peek through the windows of Christopher Martin Gallery and other high-end art spaces where works routinely sell for six or seven figures
• Spot the unmarked door of the ultra-exclusive Caribou Club, an invitation-only establishment where Hollywood royalty, tech billionaires, and actual royalty gather behind closed doors
• Admire the charming uniforms of Hotel Jerome’s staff

By the end of this walking tour, you’ll have a sense of the Aspen beyond the champagne glasses. It’s a place where wealth meets wilderness and where, even today, you can feel the wild heart of the mountains beneath its glittering surface.