Top Aspen Private Sightseeing Tours

Aspen is a town where the mountains are steep, the parties are legendary, and the truth is often stranger than fiction. On this self-guided walking tour, you’ll discover the rebellious spirit and untold stories behind Aspen’s glittering facade, from counterculture movements to celebrity hideaways. 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. 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. 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.