Top Aspen Private and Luxury

Aspen may known for glitz and glamour today, but like many Colorado mountain towns, it started as a humble mining town. Follow your guide as he shares history, local folklore, and insider knowledge of downtown Aspen. The tour happens rain or shine, so dress appropriately for mountain weather changes and come prepared to immerse yourself in local legends.

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.

Discover Aspen’s charm on this engaging one-hour walking tour, perfect for first-time visitors or those short on time. Explore iconic landmarks like the Wheeler Opera House, Aspen Art Museum, and Wagner Park while learning about the town’s rich history, culture, and vibrant community. With a relaxed pace and insightful commentary, this tour offers a delightful snapshot of Aspen’s unique character.

Summer Season Only (May - October) This tour is a light hike that traverses through park space and trail networks through Aspen's East End and loop through the lower Hunter Creek. Guests will enjoy the natural beauty of Aspen along hidden riverside paths and quiet neighborhoods while learning a bit of Aspen's history and culture. This is a great activity for guests that are looking to explore Aspen a bit and get a little exercise. This light hike is a moderate level of difficulty. Guests should be prepared to hike along uneven dirt and rock trails with some elevation gain. This light hike will encounter uneven surfaces and dirt paths with some elevation gain.

Aspen is a city nestled in nature and soaked in history. Get a sense of how the city is situated in time and place with this walking tour. Stroll through the Victorian West End neighborhood and into the John Denver Sanctuary. Learn more about Aspen’s history through its distinct architecture and the natural world.