Gay owned Legends produces and promotes fear year-round

By : Dylan Drobet
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Kissimmee – It’s Halloween season, and in Central Florida, that means spooky theme parks and over-the-top attractions.

But not every haunted attraction is under the dome of Disney, Universal or Busch Gardens.

Beyond the well-known tourist attractions, there is Legends Dark Amusements, a gem at Old Town. And the screams at this attraction don’t stop after midnight on Oct. 31. Legends is a year-round haunt thanks to partners Jim Shackleford and Jay Westerman, who created the attraction with business partner Dan Carro.

Shackleford’s fascination with all things Halloween started when he was only six years old. When his grandmother’s friend did a haunted house in her garage for the children from Church, Shackleford jumped right in to help and caught “the bug.”

As Shackleford grew up his love of haunts continued. Along the way, he found love when he met Westerman, owner of Obscurities Tattoo and Piercing.

During a visit to that studio,Shacklefordstarted a conversation with Wastermanabout an upcoming haunted house convention. This shared interest lit a spark, which led them into a relationship that reaches five years this fall.

“We connected over haunted houses,” Shackleford laughs. “It’s always been woven into the tapestry that is my life. Neither of us knew if the other was gay or straight at the time. I’m not usually very aggressive but I Facebook-stalked and the rest is history.”

The duo started the company in Dallas and had intended to open locally but couldn’t find the right location. After three years they made a connection with Carro in Orlando. Carro knew about an opportunity in Central Florida that he thought would be the perfect project for the three of them to embark on as a team. With Shackleford and Westerman’s families being scattered across Oklahoma and Dallas, the decision to open up shop in Orlando was a difficult one. It took five meetings with Old Town for Shackleford to solidify the spookyattraction as an Orlando destination.

“Ultimately it was every haunter’s dream to have a show open year-round,” says Shackleford. “Orlando really is where the world goes for vacation and with all the different cultures vacationing—literally there is a different audience every couple of months—it made sense. Outside of Las Vegas there really aren’t many. There are a handful of cities that could make this work.”

Legends just celebrated its one-year anniversary and has built an audience that even includes “Legends Superfans” who come as often as every weekend to the haunt.

While most haunts are open from mid to late September and close after Halloween, Legends did about 16 seasons worth of traffic in its first year alone and has received critical acclaim. It was voted one of the top 10 year-round haunts by The only other Floridian attraction to make the list—Disney’s Haunted Mansion.

As with most haunted attractions, theme is key. Legends has gone with “Ashdown and Son’s Undertakers” to set up the spooky plot.

According to Legend’s website, the fictional family has offered affordable, high quality funeral services to the good people of Old Town since 1889.While they have laid many clients to rest some of them were still alive upon burial, and now the dead won’t stay dead.

The Ashdown’s aren’t the only ones who have made a living working with the dead. Shackleford gained his eerie inspiration for the haunt from his time working in funeral homes through his early 20s and from questioning universal fear.

“We have to appeal to not just Central Florida, but Asian tourists and Brazilian and English tourists,” he explains. “Our audience is so varied culturally that we had to figure out something universally that cultures share: death is a common fear. It’s the final great mystery.”

So what is it that Shacklefordfears? Since growing out of his childhood fear of the dark, there doesn’t seem to be much of anything that frightens him.

“Well Jay said I should be afraid of losing him,” he laughs. “Really my biggest fear is failure. I want to be at the top of my game with whatever I am doing on a business and personal level.”

It seems failure hasn’t been an issue for Legends or for life partners Shackleford and Westerman.

“Because we are still in the process of relocating we don’t get to work together as much as we would like,” Shackleford says. “If we’re apart for too long it is really hard for us. We are an example of yin and yang. Even in life we work through things and it’s always very civil. Jay also said he has the flower shop on the speed dial just incase.”

Legends boasts unique sets and designs that cannot be found anywhere else. One of the more noteworthy props is the “dead” body lying in a casket within the tour’s chapel scene. That body is an actual body cast of Shackleford.

“First for us, we are performers and wanted to create a custom-tailored experience,” he says. “We didn’t want off the shelf things that you could get at any other haunted house. Having custom work for us was about pride for our craft, passion and wanting to offer a unique experience.”

“We get a lot of people that ask us, ‘how can you compete?’ with the big name haunts, like Howl-O-Scream and Halloween Horror Nights, and it really isn’t a competition. An apple and orange are both fruit but we don’t taste the same. You can’t compare the two things. We have been to both events already this year. We knew the caliber of what we did had to be high because of where we are.”

While Westerman is often involved in the performance aspects of Legends, Shackleford uses his BFA and MFA in design to focus on the construction and design of the always-evolving haunt.

Legends: A Haunting at Old Town is open Thursday-Sunday from 7-11 p.m. The Stuff of Legends gift shop is open from Tuesday-Sunday form 7 p.m.-11 p.m. General admission to the haunt is $15. Legends has also offers a haunted history tour with tours on Tuesday and Wednesday nights.

For more information, visit

Photos by Patrick O’Connor.

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