Join a local and enthusiastic guide on a classic stroll through historic downtown Aspen highlighting the legends and lore behind iconic landmarks.  This tour brings a deeper understanding to what makes Aspen one of the greatest mountain towns in the world. This is a great activity for either first time or long time visitors.

Aspen's Past to Present Historic Tour

Summer Season Only (May - October)

This tour is a walk through Aspen's Victorian neighborhood of the West End and along the nature paths connecting to the Roaring Fork River. Aspen's story is unraveled through the stories behind victorian and modern architecture and Aspen's connections to it's natural surroundings. 

Distance traveled is about 1.5 miles with some minor elevation changes. While a majority of the walk is along paved surfaces there are some uneven natural paths. Participants should have a moderate physical fitness level.

Aspen's Off the Beaten Path Tour

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.

Aspen Self-Guided Tour: Tales of Wealth, Wildness and Rebellion

This is a fun snapshot of this great mountain town, highlighting Aspen's culture & possibility.  Easy going pace and delivery.


Highlights of Aspen Tour

Let's Roam is the top app-led adventure hunt company! Discover the best landmarks and hidden gems, answering trivia questions and tackling exciting challenges along the way. 

Team up or compete against each other as you uncover new facts and create unforgettable memories. Let's Roam Adventure Hunts are perfect for any occasion—whether it's an everyday activity, a bachelorette party, a birthday celebration, or a corporate team-building event! 

Each player chooses an interactive role, with unique challenges for everyone.

Historical Tours in Aspen

Aspen's Past to Present Historic Tour

Aspen's Off the Beaten Path Tour

Aspen Self-Guided Tour: Tales of Wealth, Wildness and Rebellion

Highlights of Aspen Tour

An Epic Scavenger Hunt: Aspen Get An "Altitude" Adjustment