Steps from Broadway, there’s a nightly show pulling back the curtain on the city’s Prohibition history. Telltale Tours is a Hell’s Kitchen-based historical guide company capturing the attention of visitors and locals, thanks to the showbusiness panache of one passionate New York actor.

Telltale Tours Rory Jenna
Telltale Tours co-founder Rory with tour host Jenna on Broadway. Photo: Naty Caez

Weekly Prohibition, NYC Speakeasy and Hell’s Kitchen Rooftop Bar tours are all based in Midtown, and guests are treated to a specialized historical bar crawl at famous haunts like The Flute Champagne Bar, Lillie’s Victorian Establishment and The Landmark Tavern (quite literally haunted). 

The booze-and-showbusiness lore of a Telltale Tour is the work of co-founder Rory Lipede, who with business partner Brock Ganeles, has developed hyperlocal historic tours based on her own experiences of exploring Midtown as an actor living in New York. 

Originally from St Louis, Rory had run the gamut of actor day jobs and was looking for something new to pay the bills between shows. “I was really exhausted by the idea of constantly being a bartender, or having to quit my job to audition — I wanted a gig that had a little bit more flexibility,” she said. “I had a friend who had a friend who had a friend who had just started a new company called The Ride.” She decided to take the leap and apply for an improv-meets-tour-guide job. 

Rory Lipede
Telltale Tours co-founder Rory Lipede in Hell’s Kitchen. Photo: Naty Caez

The gig led to another more formal tour job, where Rory studied the Blue Guide New York tour bible and received her official guide license. “I felt like I had found my niche,” she said. “Not only did I get to hang out with people, but also to share information about New York from a minority’s perspective.” 

Rory enrolled with tour groups all over the city, and while she found it fulfilling to share New York City history, “It was tough at first because a lot of people wanted me to always do the Black history tour or they’d already had their ‘Black tour guide,’” she said. “ It was interesting breaking into the industry as an African American female who also talked about European as well as Hispanic and all backgrounds. I didn’t want to be moved into this corner,” she added. “Because I’m not just Black — I’m Scottish, Irish, Norwegian, English, it doesn’t end with Black.” 

Patrons can try Prohibition-era cocktails at one of Midtown’s first speakeasies, The Flute Bar. Photo: Naty Caez

Continuing to break boundaries throughout the touring industry, Rory eventually worked her way up to be a well-regarded Airbnb Experiences host. It was at an Airbnb function that Brock, attending with a friend, noticed Rory’s talent. 

“The friend I was with said, ‘Oh, she’s the number one host in New York City’. She was like a celebrity,” said Brock. “I was running a company that did online reservations for nightlife, and had been approached to create some nightlife tours and I thought that there was a great opportunity to make a nightlife business — but you had to be really good at it.” After watching Rory work, he “was basically pitched on the idea of helping her develop this into a big business — because I think she’s the star of the show and a creative genius.”

They went into business together to found Telltale in 2015, with Brock running the “behind the scenes” operations and Rory, as Brock put it, “the front-facing genius of developing the tourism programs and training all of these amazing actors to be our hosts.” 

When it came to coming up with a unique historical tour program, Rory knew that Midtown was an under-utilized setting. “It’s a difficult place to pull off,” she said. “There’s a different dynamic than some other neighborhoods with the influx of tourists, businesses and everything that surrounds it, and I also wanted to make sure that people could go to the theater afterward.”

“It was really hard in the beginning,” said Rory, who worked diligently to make inroads with local watering holes. “The first establishment that was gung-ho was The Flute Bar,” and soon enough, more followed. 

Slowly but surely, Telltale developed a series of Hell’s Kitchen-based tours — each one a little different, giving guests “the history of Prohibition and the ties in each establishment that attach it to Prohibition,” Rory said. “On top of that, we have guides as that come from all walks of life and they are allowed to bring themselves into the tour — so each tour has its own twist.” 

They relaunched in 2022 after a COVID pause. “I definitely think there’s this new version of Hell’s Kitchen post-pandemic. I turn a corner and am like, ‘What’s here now?’ Whereas before I was much more familiar with every corner,” Rory said. “There’s an element of ‘old meeting new’ and it’s a chaotic moment to study, but out of chaos comes beauty — there’s a real heartbeat to this area that I think people are missing out on.” 

On our tour, we learned that Lillie’s Victorian Establishment used to be a Catholic Church. Photo: Naty Caez

“We get visitors to New York, and they don’t know Hell’s Kitchen,” said Brock. “And then they’re introduced to this great neighborhood.” In addition to showcasing perennial favorites, W42ST newcomers like The Dickens and The Friki Tiki are welcome discoveries that they plan to incorporate into future tours. 

The W42ST street team got the chance to tag along with tour guide Jenna and an intrepid crew of bar goers ready to trade last week’s wind and cold for a tipple and some Prohibition tales. And despite being hardened, know-it-all locals, we too learned some fun new Prohibition facts. We were regaled the tale of legendary speakeasy operator Texas Guinan, whose bootleg booze still sits hidden in the ceilings of the Flute Bar, and who knew that the dining room at Lillie’s Victorian — once a Catholic Church — contains effects from the personal estate of socialite and actress Lillie Langtry, who became famous when, on the eve of her Broadway debut, the theater burned down. Our history lesson was topped off with a serving of Prohibition-era mixology education, where we were guided to try cocktails authentic to the time period being discussed. 

More than anything, Rory highlighted the joy of having established long standing relationships with Hell’s Kitchen business owners during her time touring Midtown. “I’ve met some of my dearest friends here that have their own bars and restaurants,” she said, adding that she was happy to see William Welles and the crew at Chez Napoleon triumph over their endless shutdown. The community Rory has built extends to the tour guests, too. “Someone from one of our tours a few months ago came back to New York, and their first stop was one of the spots we brought them to,” she said. “It’s really cool to see that.”

Back on our Prohibition tour, Host Jenna agreed. “I love it when I see people who don’t know each other become friends,” she told W42ST. “I had some folks from Malaysia on a recent tour who told me ‘I now have a place to stay when I visit!’” 

“We want to bring business to the neighborhood,” said Brock. “Yes, people are buying tickets to the tour. But then they’re spending money at each of the venues that we go to,” he added. “We like to think of ourselves as something of an economic stimulant to Hell’s Kitchen.” 

Chez Napoleon owner William Welles, a guest and Rory at Lillie’s. Photo courtesy of Rory Lipede

The team at Telltale is planning to expand their reach throughout Hell’s Kitchen. In addition to the newly developed rooftop tour, they will be rolling out additional seasonal routes and special edition tours. “We test them out, and if they work with our customers we stick with it,” said Brock, “and if not, then Rory creates another phenomenal tour and we try that.” 

Telltale Tours run at 4:30pm and 7:30pm, and are available to book here.

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  1. Diana and I met Rory and friends at Landmark Tavern over the summer randomly at the bar, and she is just the nicest! Tours are such a fun way to discover and learn about new places.

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