A Most Illegal Adventure with New York City’s Wildest Underground Event Planners

On a rainy Saturday night in October, a group of 100 strangers have converged on the Waldorf Astoria hotel for an unsanctioned scavenger hunt. Dressed in formal business attire with official-looking name tags, the 19 small teams attempt to blend in with the well-heeled clientele as they race around the hotel for three hours, checking absurd tasks off their lists. Take a picture hugging a guest while wearing his or her bathrobe? Check. Gather the “company” into a maid’s closet? Check. One participant strips down to take a bubble bath in a momentarily empty room. Others deliver room service.

When security catches on (“There’s one group booked here and this isn’t them,” a guard is overheard telling his colleague.) and begins cutting off elevator access to certain floors, attendees slip into back stairwells and, later, freight elevators.

Some planned pop-up activities, like ballroom dancing lessons, have to be scrapped. But the finale to the illicit event goes on as planned: the 80 people who stick it out make their way onto the roof of the hotel for a secret show replete with a burlesque-dancing opera singer, an accordionist, and an upright bassist. Below, midtown New York City literally sparkles.

October’s Waldorf infiltration was the most-recent brainchild of Wanderlust Projects, a two-person team developing trespassing adventures. In the city that never sleeps, a speakeasy revival over the past half-decade has created an appetite for entertainment built on exclusivity and secrecy—underground dinner clubs, 1920s-themed jazz parties, and prohibition-style bars.

But there’s another, more dramatic movement underway, one grounded not in the superficial facade of privileged rarity, but rather in creating singular, life-changing, and possibly illegal experiences in abandoned locations. This underworld scene was once comprised of a small, private community of insiders, often called urban explorers, who were intrigued by off-limit places. But the relative-newcomer Wanderlust wants to change that. Founders N.D. Austin (who also goes by Nathan) and Ida Benedetto are prying open their guest list and giving the wider community unauthorized permission to experience the forgotten, roped-off corners of their city.

Austin and Benedetto joined forces after meeting as neighbors in a former factory building in Dumbo, Brooklyn. At the time, Austin was working as a video editor while finding unusual spaces to host simple events in his spare time, and Benedetto was building more complicated professional events for clients of her social good game-design company.

On first impression, the two make a strikingly disparate pair. Thirty-one-year-old Austin is both passionately verbose and enigmatic, prone to saying things like, “I can tell you about it, but I can’t tell you anything about it.” He’s slight, with a dark fedora almost always perched on his curly dark hair, and a mustache expertly curled upward, like a villain in a silent film. Keeping the hours of an owl, he does most of the location scouting and exploration. Benedetto, on the other hand, is a diplomatic and put-together 29-year-old, with soulful eyes, a bob of red hair, and no-nonsense manner, who tackles the complex task of interactive experience design. Her straightforward approach to answering questions and Austin’s circuitous responses are entirely at odds.

What they do share is unhappiness with not just the official constraints of New York, but also the limited scope of most underground trespassers, often called urban explorers, who are committed to keeping the abandoned sites they find secret from outsiders.

“There’s often a sense that if you publicize something that’s off limits, and then people start going there, it’ll become ruined, it’ll get blown, it’ll get busted, it’ll get hot. And then the people who matter won’t be able to go anymore,” Austin says. “I think spaces belong to a much wider array of people than just those with urbex cred.”

The Wanderlust team calls their work transgressive placemaking: they tailor immersive experiences around specific, and preferably history-rich, locations. “We’re giving people permission to go somewhere that they usually do not have permission to go, and we’re usually doing that illicitly,” Austin says. The attendees aren’t customers or guests, they’re complicit participants—no spectators allowed.

This model isn’t new, but allowing outsiders to join in is. In opening up their events, Wanderlust hopes to bring a wider awareness of endangered spaces to people who will build their own underground experiences and enliven them.

“What’s interesting to me about Wanderlust is they’ve taken the impulse [to explore] and combined it with something much more interesting,” says Jeff Stark, a New York event designer who seems to have his hand in most of the city’s underground happenings. “They’ve really made it a point to figure out what they’re going to do in those spaces.”

The group recently launched onto the New York scene when Austin, with help from his partner in crime, Benedetto, opened an eight-weekend-long springtime speakeasy called the Night Heron, inside an empty water tower on the roof of an abandoned building in Manhattan. The project was produced on a size, scale, and complexity previously unheard of in the insular community of underground event proprietors. From March to May, 700 guests streamed in and out of the bar, which sported keyboards as tables, live music, and unusual guests. On any given night, attendees could find someone like Jesse Sheidlower, president of the American Dialect Society, mixing drinks for the likes of actor Edward Norton, while an accordionist, trumpeter, and bassist serenade them from a built-in perch.

When the subsequent press in The Atlantic, the New Yorker, and the New York Times published after the speakeasy’s closure, readers were left buzzing with curiosity and desperate to find out how, next time, they could be in the know. The random nature of the guest list made it seem like, for once, those unaccustomed to breaking into abandoned buildings could finally snag an invite.

The Night Heron is the event most have heard of, but there are a handful more that have passed under the radar. Wanderlust has executed six guerilla-style adventures since launching in the fall of 2012. Their portfolio includes: a weekend couples getaway at a decrepit ’70s honeymoon resort, a “Candyland Trespass Safari” through Brooklyn’s soon-to-be demolished Domino Sugar Factory; a love motel-turned-birthday party in Brazil; and the scavenger hunt through the Waldorf Astoria.

After the publicity from Night Heron, Wanderlust experienced a firestorm of media attention and inquiries from people interested in infusing their brand or event with some transgressive magic. But they reject the label of, as Austin puts it, tour guides “for hire for anybody who wants to get into something they don’t know how to get into.” Instead, they want to inspire and train others as copycats. To that end, they partnered with oddity website Atlas Obscura over the summer to host “The School of Transgressive Placemaking.”

In four sold-out workshops in June, a variety of leaders from various fields—including a former Bronx district attorney and the creator of Improv Everywhere—educated a rapt audience on how to stage their own events. Classes ranged from the legalities and safety of urban exploration to site design and event documentation. The groups that operate within this realm of event planning differ vastly in concept and execution, but for most, the aim is to create an immersive experience that is the antithesis to attending a Broadway show or going to an art gallery. Wanderlust is the first to take solid steps to make this world accessible to a broader community, encouraging others to plot their own parties instead of asking, “What’s next?”

The entrance bar isn’t high: you don’t need to shell out for a venue or hire caterers and bartenders. You do need a heavy dose of creativity, an understanding of the risks, some trusty collaborators, and a penchant for adventure. To get started planning your own crazy, risky, and life-changing escapade, look around: There’s no shortage of incredible settings.

Tip 1: On the Prowl for Abandoned Spaces

In Wanderlust’s ethos, place is the main character of an event. So naturally, the first step to creating an experience is to find a worthy location. Austin takes on the bulk of the physical scouting, prowling the streets in search of interesting sites. “He kind of can’t not be exploring things,” Benedetto attests.

Trace it back to an unconventional upbringing. Raised in the 60-person community of Game Creek, Alaska, Austin’s parents were members of a fundamental, apocalyptic Christian movement called “The Move.” He spent his childhood constructing log cabins and exploring the wilds. When he arrived in New York in 2008, he was disillusioned with the restrictions around places he wanted to explore, and began planning little transgressive get-togethers, like games of croquet in abandoned Williamsburg lots.

To find a location, all you need is a trained eye and the patience for research. When picking the spot for his next event, Austin does some urban espionage: first observing potential sites and digging into their histories. Once he pinpoints a place with potential, he starts the physical site exploration. He found the Night Heron’s water tower by looking through the Buildings Department records for structures with violations and fines, which usually signify absent landlords. Then, he scaled at least 30 water towers with a few like-minded friends to take a look inside.

Gaining access to abandoned or decrepit buildings doesn’t necessarily require fancy tools. “The world is porous and full of holes…so you just find the cracks,” Austin says slyly. “If you’re wandering into some place you can plausibly say you wandered in. If you wander into some place and you have a lock pick set, and a cutting torch and bolt cutters, then, possibly, you’re up to burglary.”

Monitoring and surveillance are painstaking work, but necessary to finding and preparing the perfect location. Before an event the Austin’s team filters through a checklist of concerns: Is the location private or city property? Does it have safety issues? Who, if anyone, is frequenting the place? Are there guards who have a routine patrol? When is the area least busy?

Tip 2: Plan A Wild Adventure

While Austin collects potential sites, Benedetto delves into their backstories, figuring out how to imbue history into the property’s current state of disrepair.

Raised in a strict Catholic family in Westchester, Benedetto became immersed in the punk and squatter movements in the Lower East Side while she was still in high school and began photographing underground events like the ones she now designs.

But it wasn’t until she met Austin that she started building her own events. When the two stumbled upon an abandoned honeymoon resort in rural Pennsylvania, they launched their first joint venture: “The Illicit Couples Retreat,” at Penn Hills Resort, a once bustling swingers’ getaway in the Pocono Mountains.

“By discovering this place that I don’t understand, I get to try and figure out why it exists the way it is, how it worked, how it works now, why it is derelict, and why it has fallen into disuse,” Benedetto says. ”What’s changed in society to create that situation?”

The task often lasts for months, involving multiple site visits. The pair traveled to Penn Hills at least a dozen times over three months, teasing out the nuances and former life of the property.

As part of their research, they unearthed documents revealing $1.1 million of unpaid back taxes that did the place in when its 102-year-old owner died in 2009; dug through the family’s history; and read all the accounts of what the infamous party spot was like in its heyday. But one aspect befuddled them: old newsletters and online comments from former employees contained countless mentions of how much the workers loved their jobs at the trashy destination.

So, for Wanderlust’s event in October 2012, they instructed their volunteer stewards to be overly enthusiastic about their work. After the guests left, Benedetto began cleaning the cabins and radioing back the condition of the rooms to the stewards, who would weigh in with the antics they overheard the night before. “It immediately erupted into this back channel of gossip,” Benedetto remembers. “And I thought, ‘This is why it was a blast to work here.’”

It was a revelation that stuck with her—the concept that embodiment breeds understanding, and that an atmosphere can transcend time. “It was only by actually enacting that that I understood what was going on there.”

Tip 3: Build the Suspense

Some spaces call for open exploration, while others, like Penn Hills, require a linear plan: a beginning, middle, and end. But Austin and Benedetto are careful not to let rules dominate. “We’re not ever telling a story: here’s what happened, here’s the plot, the antagonist,” Austin says. The result should be a personal tale, your own unique journey. The challenge is maintaining a feeling of unstructured spontaneity to foster a sense of adventure, while the experience is actually being meticulously orchestrated.

Wanderlust only reveals a few details to guests before the event, not much more than a meeting place, time, and a stern warning about the illegalities of the adventure. The form of the event—where you’re going and what you’re doing there—stay hidden for as long as possible. It’s something Austin describes as “a striptease of information,” tantalizingly revealing only enough to “awaken and excite the senses, so people are in a more receptive state.”

Then, as the event begins to unravel, guests are brought into a space normally deemed out of bounds. The act of crossing that boundary, entering what’s called “The Magic Circle,” has to be a little risky, something to spike the adrenaline and allow a different persona to come out. “Once you have trespassed, the regular rules of your life don’t apply anymore,” Austin says.

Alexandros Washburn, New York City’s chief urban designer at the Department of City Planning is a forthcoming and unexpected proponent of Wanderlust’s work. He says the interactions Austin and Benedetto are building intertwine with his day job.

“In a way, Nathan and Ida mentor people to look at the city in new ways,” he says. “Cities are so complex that you need some sort of framework or guide to help you go through the layers. The physical traces of the city can tell you not just what happened—but who we were.”

Laughingly, he acknowledges that he “obviously can’t condone their methodology,” but he shares a similar end goal with them: “to let people see their surroundings and themselves in a new way.”

And Benedetto and Austin think their efforts are, so far, working. “All those people who went to the Night Heron, now they look up and think about rooftops differently,” says Benedetto. “That’s the success—they see potential where before they didn’t see anything.”

Tip 4: Open Those Checkbooks (Or Don’t)

In the country’s finance capital, not monetizing a viable business plan is seen as downright foolish. But charging upfront for their services, Benedetto says, is the “least creative option,” and creates a commercial relationship between planners and guests. Though producing an event isn’t cheap, Wanderlust operates entirely on a gift economy and the pay-it-forward approach hasn’t sent them to the poorhouse quite yet.

“The value we get back from doing that is huge, even if it’s not necessarily in dollar figures,” Benedetto says. Gratitude from attendees has taken forms ranging from tickets to a Broadway show, to a trip to Brazil to conduct a workshop. A few events have been underwritten: the Illicit Couples’ Retreat was backed by a $1,000 grant from the Awesome Foundation, a micro-grant organization for unique projects. And two guests from that weekend getaway later pitched in a small amount to cover costs at the Domino exploration.

The best way to keep costs down is to tap a crew of skilled friends to work the event. “No one does this stuff professionally so it’s always an adventure for them,” Benedetto says. “If at any point it started to become work then we’d be doing something wrong.”

She recommends finding co-conspirators you know and trust. Each event demands a variety of skillsets and manpower, ranging from security and EMTs to carpenters, actors, and even opera singers.

But the scale of a gift economy is still limited, requiring tight guest lists that often lead to a misperception of Wanderlust’s work. “We’re not trying to create exclusive experiences for the sake of closing other people out, we’re doing it to create the most transformative value for the volume of people we can actually accommodate,” Benedetto explains.

Tip 5: Are You on the List?

But a tight guest list doesn’t mean a predictable one. In fact, a more diverse group of participants is exactly Wanderlust’s goal. In the past, underground events have operated in close-knit circles, usually involving either those personally connected to the creator or intrepid explorers actively seeking the experience. But Austin and Benedetto are trying to build a different, broader group of explorers by, as fellow designer Jeff Stark says, “showing people how to open spaces, think about them in a different way, and expecting people are going to make that leap themselves by creating their own events.”

In their effort to attract outsiders into the underground, Wanderlust has had to deal with the difficulty of bringing new participants into such an intimate and mutually high-risk venture.

The Night Heron was the first adventure Wanderlust opened up to an audience larger than a pre-set guest list. To strike the delicate balance, Austin and Benedetto used a six-degrees-of-separation rule to ensure all participants were vetted by the person before them. Austin got creative to ensure it was followed. A pocket watch purchased by guests for $80 to $300 (the price rose as time passed) during the Night Heron’s run served as a transferable invitation to be gifted to a friend. That friend could then pay forward the invite by buying a watch to pass on, and so on.

With the watch, Wanderlust found a way to cover costs and ensure a varied and trustworthy clientele. The friends-of-friends guests came to include celebrities like actor Edward Norton, Amanda Palmer of the Dresden Dolls, and Girls star Adam Driver, all of whom mingled comfortably with the non-famous. Spurred by this success, Austin and Benedetto plan to loosen control over the guest list even more for future events.

Tip 6: Beware the Dangers

To keep problems and surprises to a minimum, the Wanderlust team obsessively prepares. They make sure to use the utmost stealth during the planning process to ensure the police don’t notice or receive calls from concerned neighbors.

They also try to predict guest behavior, speculating where participants could wander and any potential dangers they may face. “This fun needs to have an illusion of choice,” says Myric Lehner, a regular on Wanderlust’s crew. The team sets up unobtrusive obstacles in front of dangerous spots to retain a sense of freedom for participants who feel like they are choosing to avoid a certain area rather than being denied access.

Once an experience is underway, it’s harder to control guest behavior. The designers have found that the strategies used to make people feel comfortable and fully immersed in an adventure also create a feeling of trust that causes the risks to be forgotten.

“There’s a level of surrender that happens that we have to be conscientious of. We can’t expect people to remember they’re in an event space, and they have to take care of themselves," Benedetto says. “We go through extreme measures to make risks clear: You are trespassing. You’re breaking the law.”

Tip 7: How to Slip Your Handcuffs

Which brings us to the pesky issue of legality. These explorers may make their name in daring stunts, but they’re anything but cavalier about the risks involved. “It’s not a military operation, but we view it like a military operation,” Austin says.

This is post-9/11 New York, after all, and there’s a chance any discerning passerby could contact the police about a darkly-clad group with bags of gear entering the subway system or climbing a bridge.

In an internal memo released in March, the National Counterterrorism Center detailed the dangers explorers pose to national security, saying their event documentation “could be used by terrorists to remotely identify and surveil potential targets.”

Wanderlust doesn’t buy what they describe as a propagation of fear, which Austin says has a “chilling effect on peoples’ relationship to the city.”

“The security measures create a tunnel vision,” says Benedetto, which Wanderlust hopes to disrupt. But in doing so, and getting away with it, are they exposing the city’s weaknesses? Wanderlust stresses a no-harm-done mantra, and their intention is not, as Austin puts it, “to poke holes in the security theater.” The holes, he admits, are inarguably a side effect, but not ones large enough to concern them.

Wanderlust has had good luck so far. Neither of the founders has been arrested, and they’re aware that it’s not in their—or the taxpayers’—best interest. “I consider [the event] failed if police are sending helicopters after you. I like to stay farther below the radar than that,” says Austin, who admits he’s successfully evaded such helicopters on three separate occasions.

The danger isn’t entirely over after the event wraps. New York City has laws that prevent the police from arresting someone for a violation they didn’t observe happening. But, for bigger charges, like a misdemeanor or felony, you can be busted after-the-fact just for tweeting a picture. It’s unlikely police will go after an entire party, but the organizers could face trespassing and reckless endangerment charges.

Tip 9: The Great Press Debate

Because of this, many in New York City’s underworld have long valued keeping their stunts and activities off the front pages. But newcomer Wanderlust has done just the opposite, hoping the publicity will encourage more explorers and attract attention to places in need of some TLC. Though Benedetto says their methods are “rising the tide for everybody,” others are skeptical.

Photographer Tod Seelie has become a fixture in documenting New York’s counterculture since arriving to the city the late ’90s, and he’s photographed much of Wanderlust’s portfolio after meeting Austin at a party atop the Williamsburg Bridge in 2011. Despite his role, Seelie offers a soft-spoken critique of Wanderlust’s propensity toward publicity, which he found “very strange” when they first began working together.

The channel for disseminating event information is larger than ever, Seelie says, bringing an awareness of underground exploits that would have previously gone unnoticed by the general public. A pre-Internet event that might have garnered a spot in the alt-weekly The Village Voice, will today reach an audience far wider with hundreds of tweets, blog posts, and photos coming from both organizers and attendees. The self-promotion, Seelie thinks, is somewhat boastful, and he wonders, is it worth it? “In the past, most people’s attitude has been no, who cares what the general populace thinks—this is not for them.”

But the Wanderlust pair is hoping the coverage will act as an invitation to other residents to learn about and explore their city’s spaces. For the most part, Wanderlust operates transparently, inviting press to about half their events. Its website dutifully features photos, descriptions, and press clippings of its major projects and offers email alerts for those interested in staying informed about the group’s adventures.

Benedetto acknowledges that their tendency to invite press to about half their events has sparked a discussion within the community. “It’s just not how people have done it,” she says. But they stress it’s necessary to bring attention to the city’s neglected spaces.

While Seelie finds their efforts to expand the explorer community admirable, there’s no telling what sort of visitors a place will attract. “You make it hard to go back, not just for yourself if you want to enjoy the space, but you make it hot for other people independent of you who also enjoy doing this sort of thing,” he remembers telling Austin and Benedetto.

Despite the publicity, a vicarious trip to the underworld via the Internet is enough for many, Seelie speculates, and that’s why the photos and first-hand accounts spread so rapidly. “To have it get so big that you’d have to get in line to get into an abandoned building is, I think, a little far-fetched,” Seelie says. “There’s enough people that are not going to be motivated enough to want to put up with asbestos and dust and wonky floors and going to jail—because no matter how you color it you’re going to be dealing with a lot of that.”

What’s Next Is Up to You

As with all underground practices that bubble into the mainstream there’s one big concern: selling out. Wanderlust plans to resurrect its workshop series in January, with a focus on bringing event planners together to discuss the ethics of doing transgressive placemaking work for hire. “There’s new attention from ad agencies that want to engage these kinds of experiences, and we don’t want to see our community of practitioners get destroyed as soon as a fast-talking guy with money comes in,” Benedetto says.

Recently, another alternative-event group accepted a tequila sponsorship for one of their parties, and the tasteless way it was structured lost them “significant credibility with our entire community,” Benedetto says. “People don’t like feeling used,” Austin adds. It was the first major confrontation on the issue of corporate involvement in the community. The same brand had reached out to Austin offering to pay for a new incarnation of the Night Heron while keeping their financial support secret under the condition that they receive a certain number of tickets. He declined. “It’s difficult to maintain intimacy and authenticity and integrity and combine that with commerce,” Austin says.

So far, Wanderlust has steered clear of opportunities that would put them at risk of losing their independent identity. The duo remains mostly mum on their plans for future events, but they did reveal that they have spent the past year dedicating one day a week to planning what will be their largest adventure yet. And they still have months of work left on it. While they are keeping details tight, they did spill the code name: “Hats and Hatchets.”

But you probably won’t hear about it until it’s over. “People often say, ‘Can I come to the next thing? Or, Where do I sign up?’ Sometimes that works, but the thing we’re really interested in is what are you doing next? What event do you want to attend? Can you make that?” Austin says. “Invite us.”

For some, crossing boundaries is just a once-in-a-lifetime experience; but for the Wanderlust team, it’s a contagious lifestyle. “I think Nathan and I make most of our lives into magic circles, it’s a matter of drawing other people into it,” Benedetto says. And while in their company, it’s not hard to imagine that you too could be sketching entrance points on unrolled blueprints, donning a radio earpiece, and directing a following of awe-struck strangers through a guerilla-style adventure that could, you warn ominously, get a less-than-vigilant person thrown behind bars.

First you have to decide: What does that no trespassing sign mean to you?