Aspen Hiking Vacation Tours & Guides
Explore Aspen’s unique and storied history with a fun and educational outing with Dean’s Walking Tours. Join professional local guide Dean Weiler for an entertaining and unique tour of the town’s rich past. Dressed in suspenders, a pair of Carhart pants and carrying a burlap satchel, Dean plays the part from head to toe, showcasing the mountain town’s storied haunts on one of his guided tours through the streets of Aspen.
Dean has been escorting guests on fun and educational walking tours of Aspen for more than 15 years. It’s the perfect outing for older guests and families with children. Tours visit popular local spots like the Hotel Jerome, Pitkin County Courthouse, Wheeler Opera House and The Red Onion restaurant.
Visitors love Dean’s authenticity, humor, kind spirit and good nature. Currently, Dean’s Walking Tours offers three unique experiences: “Aspen’s Past to Present,” “Aspen’s Darkside” ghost tour, and “Glimpse of Aspen.”
Aspen’s Past to Present Tour
This 90-minute guided walk though downtown Aspen retraces the town’s humble beginnings as a silver mining town all the way though its evolution into a skiing Mecca. Along the tour, Dean spins local yarns ranging from Indian legends to mining folklore while pointing out key structures and remnants around downtown. It’s a perfect all-encompassing history of Aspen.
Aspen’s Darkside Tour
Do you believe in ghosts? If not, Dean might change your outlook on things. Dig into the town’s dubious history of murder, mystery, mayhem and the paranormal on this 60-minute guided downtown tour that takes place in the early evening. Explore Aspen’s dark side as you walk though cemeteries and other haunts as Dean explains the significance of each creepy location. You’ll hear ghost stories that are sure to leave you a little spooked.
Glimpse of Aspen
Looking for a quick sample? Sign up for Dean’s 60-minute walking tour called a “Glimpse of Aspen.” The quick walk showcases downtown’s hearty culture, fine dining and retail shopping experiences. Breathe in the fresh mountain air as Dean shows you all the high points of downtown. It’s the perfect orientation for first-time visitors. The easy walk is a great way to get acclimated to the high altitude before hitting the slopes.
Have a family gathering, destination wedding, business retreat or ski group coming to Aspen? Dean offers custom private tours to accommodate larger groups. Walking tours can be a fun diversion from a strenuous business meeting or a unique outing for a wedding party. Dean will custom-tailor experience for larger groups upon request.
If you’re planning on taking one of Dean’s Walking Tours, here’s what you need to know:
- Walking tours do not require anything strenuous walking and typically cover 12 blocks or less.
- Tour sizes range from four to 10 guests and tickets and reservations are required.
- Tours are not cancelled due to weather, so guests should dress accordingly.
- Horse-drawn carriage tours are available for smaller groups.
- No pets are allowed on the tour.
- Gift certificates are available to purchase for future walking tours.
- Guide tips are encouraged but not required.
- Dean is also available to hire for special storytelling events.