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Macabre Mountain Tales Abound On 'Aspen's Dark Side' Tour

Oct 31, 2019

Dean Weiler delivers a spooky story in front of the Red Onion. He leads "Aspen's Dark Side" tours year round.
Credit Alex Hager / Aspen Public Radio

It’s a dark October night in Aspen, and there’s a chill in the air. That’s not unusual for late fall in the Rockies. But tonight, there’s even more reason to feel a shiver. We’re on a journey through decades of macabre mountain tales with a tour called “Aspen’s Dark Side.”

Our tour is led by Dean Weiler, who does this for a living. Tonight, he’s dressed in a vest that wouldn’t look out of place in the 1800s, and a rather dashing top hat to help set the scene.

He delivers the night’s first ghost story in front of the Red Onion, Aspen’s oldest bar. It should come as no surprise that in the 127 years it’s been open, there have been at least a few stories of barroom visitors from beyond the veil.

One of those is chronicled in an anecdote from one of the bar’s bouncers. 

“He’d be in the Red Onion Late at night,” Weiler says. “All alone, restocking the bar, down in the basement moving kegs of beer around when he’d hear footsteps on the floor above him. He’d rush upstairs to see if somebody’s there. But nobody’s there.”

 

"He'd hear footsteps on the floor above him. He'd rush upstairs to see if somebody's there. But nobody's there."

After the stop at the Red Onion, it’s on to the Pitkin County Courthouse. Weiler starts telling a tale from the mid 70s about a girl who was found murdered by the side of the road in Snowmass. Police in Utah tracked down a suspect and it started to look like he might have been the killer. 

Weiler says the suspect was brought in to a jail cell in the basement of the Pitkin County Courthouse, and as he goes on to describe the man, he starts to sound familiar.

“Some people tell you he’s very handsome,” Weiler says. “Very intelligent, very charming. Takes us a little longer to realize he’s also very psycho. A serial killer you may know by the name of Ted Bundy.”

 

 

"Some people tell you he's very handsome. Very intelligent, very charming. Takes us a little longer to realize he's also very psycho."

The story doesn’t end there. Weiler goes on to tell about how Bundy escaped the courthouse behind him as well as a jail cell in Glenwood Springs. And then, how, years later, bars and restaurants were full of celebration the day Bundy finally got the chair.

“Some gave out free drinks and free shots,” Weiler says. “But others, they shut off their lights, so he could get all the electricity he needed.”

Our penultimate stop on the spooky stroll takes us just down Main Street to the Hotel Jerome.

In the nearly 13 decades it’s been in town, stories abound of guests who’ve encountered apparitions.

There’s the ghost of a little boy, who appears in rooms dripping wet or leaving unexplained puddles on the floor. He may be someone who drowned in the pool decades ago.

And one of the Jerome’s resident poltergeists seems to think she’s part of the hotel’s staff. 

After years of working there, one of the maids at the Jerome quit out of the blue. Management was confused at first, until they asked her why she left.

“When they followed up with her to see what happened,” Weiler says. “She just said, ‘Well, I’m sick of working with her.’ The spirit maid that followed her around all night long, played with everything she did.”

Finally, our tour takes us to Galena Plaza, where you can barely make out the silhouette of Smuggler Mountain against the cloudy night sky. Weiler closes the night with a story from the mining days that put Aspen on the map.

The men who worked in those early mines in the hillsides around town told of creatures that patrolled the tunnels and gave miners a warning when things were about to cave in. They’re called tommy-knockers, and they’re an essential part of early mining lore. 

But if you were to ask some of the men who spent their days deep inside the mountain, those weren’t tommy-knockers they heard, but the spirits of those who died, and they came with a far more sinister purpose.

 

“They’re not knocking out warnings,” Weiler says. “They’re knocking out mine tunnel supports, causing the cave-ins and collecting more souls.”

 

 

"They're knocking out mine tunnel supports, causing the cave-ins and collecting more souls."

After trekking across town and making our way through centuries of local legends, the tour group dissipates into the night. 

But after hearing about the spirits and spooks that continue to haunt Aspen, we’ve got plenty of reasons to check over our shoulders on the way home.

Correction: In an earlier version of this post, we indicated that the Red Onion has been open for 172 years, when in fact it has been open 127. We apologize for this error.