Diki Wackenstedt

Diki Wackenstedt is the Grilled Cheese Lady, and has been operating The Grilled Cheese Cart in Telluride in the summer and Mountain Village in the winter. She’s looking to end her long, successful run and spend more time with her grandson in Southern California. (Photo by Suzanne Cheavens/Telluride Daily Planet)

The orange umbrella that pops up on Main Street adjacent to Elks Park is as sure a sign of summer as Ajax’s tumbling waterfall or the chirr of a broadtail hummingbird in flight. In the pool of shade it casts, Diki Wackenstedt is a study in constant motion as she assembles countless grilled cheese sandwiches and keeps up a steady stream of friendly patter with her equally steady stream of hungry customers.

Wackenstedt has operated The Grilled Cheese Cart for eight years, cultivating a clientele that ranges from dedicated locals and second homeowners, to visitors from out of town attracted by the aromatic lure of what might possibly be one of America’s favorite sandwiches. Through word of mouth primarily, she jokes she’s created a “mini-monster.” But it’s a job she embraces with good humor and a sense of purpose.

“Every job I’ve ever had, I have to have a purpose,” she said.

And the purpose of her daily work of buttering bread, loading it with cheese and sliding onto the grill?

“I try to make it an extra special experience, a positive experience,” Wackenstedt said. “I want it to be part of the experience of Telluride.”

There is little doubt Wackenstedt loves Telluride. The Southern California native was nearing retirement from what would be a 30-year career of running Halloween stores — you know, those giant, seasonal emporiums peddling every kind of costume and accessory you can imagine. “You can be anything you want,” she said of her previous career. “It’s a special day.”

Casting ahead to what would be her next chapter, she took a road trip to Colorado in 2002 to explore and consider her next steps. Telluride was her first stop on a list of a dozen mountain towns she visited and it was the one that struck a chord. She, like so many of us, fell in love. She decided she would figure out a way to make it work, she recalled.

“I kept looking at the carts,” Wackenstedt said. “I love being outside.”

In 2011, she closed her stores and in 2012 pulled a permit for her first cart, which sold aebleskivers. The Danish treat — a light batter cooked in a specialty pan that gives them their spherical shape and often served with jam — though tasty, didn’t catch hold. Wackenstedt, who is half Danish, said, “Not enough people got it.”

She went back to the drawing board and hatched her plan B. The Grilled Cheese Cart was born. She’s been operating on Main Street for eight summers in Telluride and for as many winters in Mountain Village.

“It’s a food item I thought people could relate to,” she said. “Everyone likes them from little kids to seniors. And it’s easy. Plus, everything tastes better on a grill.”

Easy is a matter of perspective. While it’s an easy sandwich to make, Wackenstedt puts hours into every sandwich. Her hours of operation are 11 a.m. to 4 p.m. daily, plus more for festival weekends when hungry late-night crowds ply downtown, but there are also the hours spent procuring locally made bread, cheese, bacon, fresh tomatoes, plus the chips and drinks she offers on the side. Add cleaning, prep and accounting to the mix and it’s a wonder she has time to sleep. A Town of Telluride cart permit requires the proprietor be open at least four days per week.

She has seemingly boundless energy and takes delight in recounting encounters of dealing with high people during her late-night hours.

“It’s past hysterical,” she said of those exchanges. “I just offer cheddar or cheddar and bacon when I do late-night. I’ll tell them that and they’ll say, ‘OK, havarti.’ But really, they’re very appreciative of the cart.”

The work ethic she said was instilled in her by her father from a very early age doesn’t allow much time for rest, but when she does, she makes the trek back to SoCal where the magnet is her family, specifically her grandson, who just turned four.

Which brings her to contemplation of her next chapter. It’s time, she said, to move on.

“I love doing it,” she said. “I see locals all day long. It’s such a nice connection with the community. And this community has been so supportive.”

That grandson is what’s driving Wackenstedt’s decision to leave the grilling to someone new.

“I want to spend more time with him,” she said.

And in her typical gotta-have-a-purpose fashion she has a plan, post-grilled cheese glory. A lifelong horse person, she wants to have a couple of therapy-certified mini-horses to take to underprivileged kids and to senior homes. “Talk about rewarding,” she said.

But first, she’s looking for just the right person to pick up where she will leave off with The Grilled Cheese Cart.

“I would love for it to continue,” she said. “Hopefully, it will be someone who loves Telluride, wants to be their own boss and will continue what people enjoy.”

Wackenstedt said it will take someone with personality and a strong work ethic. She’ll aid in transitioning the new owner with both the Telluride and Mountain Village carts, and notes that the potential to grow the business is limitless. Like her, she hopes the next generation of grilled cheese purveyor will love Telluride as she does — for its scenery, history and wildlife. “That would be the ultimate.”

As much as she’s enthusiastically looking ahead, the thought of bidding her many customers farewell is bittersweet. “It will be a sad goodbye.”

We all feel that way, too, Diki.

For more information about Diki Wackenstedt’s business, contact her broker Greg Wills, Touchstone Business Advisors LLC at 303-660-3992 or gwills@touchstonebiz.com.