A seemingly ordinary delivery truck used as part of Great Gotham Challenge’s 2024 puzzle hunt

“I…think one of us needs to crawl into the delivery truck?”

A few minutes earlier, the four of us received a message on our phones from GGC headquarters: go down a particular street, and be on the lookout for a delivery truck. Once there, we should be prepared to open up a cardboard box. The delivery truck was parked on the street corner as expected, packed floor to ceiling with packages. But there was no package waiting for us to grab. Instead, the bottom left corner of the truck featured what almost looked like a tunnel, just big enough to crawl through.

So, we sent a volunteer through the hole, into the unknown. When they emerged on the other side, a man handed over a UPS envelope, and told them the password to unlock the next set of instructions. It provided descriptions of a series of five individuals we’d need to encounter in order to proceed further. Assuming the UPS envelope might contain further instructions, we opened it up.

A rotating wheel of colorful characters that popped up out of our very special UPS delivery

Upon unsealing the envelope, a three-dimensional papercraft contraption popped out of the envelope thanks to the tension releasing on a series of cleverly concealed rubber bands inside the puzzle. This time, we had to solve a logic puzzle to figure out the code word to unlock the next step in our journey.

This sequence of events took place as part of GGC:MMXXIV, an outdoor puzzle hunt that serves as Great Gotham Challenge’s flagship event of the year. Over the course of 4-5 hours, the game leads teams of up to four players through a neighborhood in NYC in order to complete a series of puzzles that take full advantage of the city and its history. Great Gotham Challenge is somewhat unique in the puzzling landscape for its focus on creating a spectacle out of its puzzles while also making the solving process feel just a bit more transgressive than it actually is.

Because this type of adventure isn’t just about solving a papercraft logic puzzle: it’s about walking down the street and realizing that even that truck on the side of the road might be part of the game…and then receiving enough validation to feel safe crawling inside.

One of my teammates, chatting with one of GGC’s colorful characters at the train station: a Misfits fan.

GGC:MMXXIV Leans in On Transgressive Moments
One of the earliest puzzles lead teams to Moynihan Train Hall’s central terminal, with instructions to find a list of colorful characters: once found, your task was to go up to the subject, introduce yourself, and shake their hands. The first character I approached was described as a businessman who lost it big while gambling in Kentucky – at one corner of the train hall, a man in a suit was loudly talking about how his horse race bets didn’t pan out. I had to interrupt his call, coming up with a pretext for striking up a conversation before doing a quick intro and shaking hands. During the shake, he palmed a few puzzle cards with words written on it into my hand.

I had less luck with a music fan described as a young person who was more likely to be a fan of The Misfits than Taylor Swift. I noticed one particular young man leaning against the stairs down to the tracks wearing a pair of prominent headphones, and sporting a festival wristband. I approached him and asked what festival he had been to, and learned he was coming back from The Governor’s Ball in Flushing – apparently The Killers and 21 Savage performed there, but my hand came back empty. He was just a random music fan, on his way home. Eventually, one of my teammates was the one to find the young woman in question, pictured above.

Randomly introducing myself to a stranger unrelated to the event at the train station was awkward for both of us, but the brief mistake was relatively harmless, and the feedback confirming I was wrong was almost immediate. Over the course of the four hours spent working through the puzzles, that wasn’t the only minor transgression we’d be asked to do. Before reaching the final location, our team had to sneak into a laundromat and grab a tshirt out of Dryer #1 (clearly labeled with “Great Gotham Challenge”). We were tasked with approaching a popsicle vendor on the High Line and telling a joke in exchange for four puzzle-laden popsicle sticks. And we went to a bubble tea shop and gave the server a password to receive an order of four drinks, with the puzzle for the next step printed on the cups.

A rival GGC team, examining a transparency at just the right spot to see a secret message

Great Gotham Challenge at its Finest Feels Like You’re Pulling Off a Heist
One of my favorite sequences from GGC:MMXXIV started off with GGC Headquarters leading us to one particular intersection on the High Line, where we were asked to look for the right perspective. While investigating the space, a teammate discovered a sticker labeled “Great Gotham Window Washing: the cleanest glass for a clear perspective“. Dialing the phone number triggered an answering machine message that provided directions for an impromptu tour of that section of the High Line, with descriptions of the surrounding area proceeding at a brisk pace.

Upon reaching our destination, we were instructed to sit down on one particular bench, and reach under it. Taped to the underside of the bench? A manila envelope, containing a transparency with one final perspective puzzle that required looking at it from just the right angle, in just the right spot. Looking at the transparency revealed subtle changes the Great Gotham Challenge team made to the surrounding area to spell out the round’s solution, only visible to those who had the right pieces of the puzzle.

Individual Great Gotham Challenge games tend to be doing their best work in those sequences of events: like how a faked historical marker sign placed in Times Square for the 2023 hunt featured a QR code that scanned to a Spotify playlist whose songs hid walking instructions to a local pizza shop. The final instructions from the playlist provided a key phrase that unlocked an order of pizza for the group, specially packaged in a box that delivered the next step. The puzzles weren’t the focus of that sequence: instead, it was the sequence itself.

While nothing is guaranteed with a Great Gotham Challenge puzzle hunt, it’s generally safe to expect to take home a puzzle-based artifact or two. The three years in NYC I’ve played have also managed to sneak in at least one snack along the way, and introduces at least one or two moments where you briefly worry that what you’re about to do is actually intended.

Not Solvable When Wet: this would be easier to read if was out in the sun instead of drenched in water

Great Gotham Challenge Works Best with Experienced Puzzlers
Even though puzzles aren’t the central focus, they do tend to be fairly complex, with the Flagship games feeling harder than escape rooms, and often even a little more challenging than many Puzzled Pint games. A lot of that difficulty comes through the complexity of the challenges themselves. Great Gotham Challenge puzzles typically come in three phases: finding the puzzle, figuring out what kind of puzzle you’re dealing with, and then going through the process of extracting a solution from the puzzle.

Instructions of where to physically go for puzzles typically involves a dose of impromptu research, as Great Gotham Challenge delights in couching its location-based clues in New York City history. So, the way our team found the location of the delivery truck was by learning that 10th Avenue was nicknamed “Death Avenue” due to how dangerous the freight line was prior to the High Line’s installation, and then finding an appropriately named local business referencing that bit of trivia.

Going to the right location isn’t always enough to spot the next task and identify what type of puzzle teams are facing, however. After reaching the laundromat and taking a tshirt, a particularly kind laundromat employee offered our team free bottles of water on an exceptionally hot day. Contrary to our initial assumption, that did not mean the shirts were printed with ink that changes colors when exposed to water. However, it did mean that the shirt was UV-treated to change color in sunlight.

That was the step necessary to see the puzzle in the first place. Even that wasn’t enough to solve the puzzle, however: savvy puzzles would then need to notice that the now-colored windows came in rows of eight, recognize the significance of that fact, and align on the proper method of reordering the message to spell out the final order. This process was lightly clued, so it’s fairly easy to go off the rails in the solving process at any of the previous steps.

Great Gotham Challenge does have a hint system built into the game’s website, where a hint to the location, puzzle type, or extraction advice can be requested for modest time penalty. For teams that are still stuck, more explicit instructions on extracting can be obtained for a larger penalty, although that still doesn’t give the solution: it’s up to teams to do the final step themselves. Because of that, it’s helpful for teams to have at least one individual who’s familiar with spotting most common cipher types: indexing puzzles, binary messages, unclued anagramming, and morse code came up during the most recent hunt.

Based on past experience, I would recommend that all but the most experienced teams liberally take advantages of hints when stuck, as the operational nature of many of the puzzles means it’s entirely possible to spend 10-15 minutes working on the wrong kind of extraction.

There’s also an option to text Great Gotham Challenge headquarters for assistance if players are well and truly stuck, or if there seems to be an issue with one of the puzzles. This was particularly helpful my first time playing a Great Gotham Challenge hunt, although the team seems to have improved considerably at risk reduction in the intervening years.

I found myself relying on those safety nets more than I might prefer for puzzle games (our team ended up taking 10 hints before reaching the finish line, which was slightly above the 6 hint average for teams on our day), in part because it was easy to get stuck on the extraction steps. The transparency puzzle proved particularly vexing to our group, as we quickly figured out what to do but finding the perfect angle and catching all the faint details was a challenge in itself. Ultimately, however these occasional frustrations are overshadowed by the magical moments of the game I just can’t stop talking about to friends and family that can only be found in a Great Gotham Challenge.

Great Gotham Challenge may not have hidden a phone inside a cake, but it did hide one in a pizza box

Let’s Give ‘Em Something to Talk About: Some Personal Favorite GGC Moments
When asked to describe the potential of alternate reality games, I’ll often reference the puzzle from the Why So Serious ARG leading up to the release of The Dark Knight, where players were directed to a number of bakeries across the country and asked to pick up cakes for “Robin Banks”. Upon picking up the cakes, players noticed that there was a phone number written in icing. Upon calling the number, the cake started ringing. Because a burner phone wrapped in a plastic bag was hidden inside.

Great Gotham Challenge’s hunts haven’t given me a burner phone yet, but every year I’ve played has had at least one moment that I can’t stop talking to people about, because of the sheer audacity it took to craft the moment…especially for an event whose tickets are priced on par with many 60-minute escape rooms in the area. So, here’s a few highlights from past Great Gotham Challenges that makes me wonder how the team could have possibly pulled the event off.

GGC MMXXIII: A Puzzle Fit for the Silver Screen

Great Gotham Challenge 2023 rented out a movie theater for a puzzle (image courtesy of GGC)

During last year’s Great Gotham Challenge event, the game’s welcome packet included a ticket for admission to…someplace. As the event progressed, our team started to suspect that one particular clue was leading us to the Times Square AMC Theater. Somewhat sheepishly, we presented the usher with our ticket, and were told to proceed to one of the theater’s screening rooms.

And in that theater, a five-minute film noir short was playing on loop, with the plot of the film delivering a fiendishly challenging puzzle forcing teams to navigate the labyrinthine New York City subway system. An excerpt from that short film can be viewed at the video above, with the paths of two out of three thugs edited out to render the puzzle as presented unsolvable.

One flame-broiled puzzle page (Image courtesy of GGC)

GGC Post Haste: Burn After Reading
Over the pandemic, Great Gotham Challenge stopped running their puzzle hunts in person, but created a number of virtual events that were run over Zoom to keep the spirit of the challenges alive. The most intricate of these events was GGC: Post Haste, where individual team members were mailed parcels to add a physical component to the experience. At one point, players find themselves referencing a custom-printed matchbook to solve a puzzle.

And then, for the final step of the experience, teams are given the following slightly ominous instruction:

While paper may burn at 451 degrees, raising its temperature to a degree slightly lower than that may mean the difference between who finishes today’s challenge victorious, and who is left smoldering.

When exposed to open flame, the card stock charred to spell out the final solution of the event: A DEAD HEAT. Rather than risk playing with matches, one of our team members placed the sheet in their toaster oven, adding some surprisingly satisfying grill marks to the final solution.

Great Gotham Challenge’s Challenge Coin, pulled from a public fountain (Image courtesy of GGC)

GGC MMXXIX: A Wishing Well, Actually
During 2019’s Great Gotham Challenge, players were treated to a particularly tasty game, with stops at Magnolia Bakery for cupcakes for dessert, followed by a chocolate egg cream for second dessert. But as a palatte cleanser between desserts, teams stopped by Washington Square Park to fish custom GGC coins out of the fountain. The coin ended up finding multiple uses over the course of the event, from its more overt role as decoder ring to a slightly non-traditional measuring stick.

Great Gotham Challenge’s elevator speakeasy

GGC MMXVIII: And All That Jazz
When asked about some of his favorite moments from Great Gotham Challenge’s ten year history, co-founder and experience designer Ryan Patch mentioned transforming an Industry City freight elevator into a jazz speakeasy, for the 2018 challenge.

The moment was particularly meaningful to him because it created an opportunity for allow players to open the elevator doors, and step into another world. Elaborating on the company’s philosophy, he explains, “We really like to think of ourselves as being in the business of creating ‘moments’ as opposed to just puzzles…often, the ‘moments’ are just gated by puzzles.”

Great Gotham Challenge Flagship Event Advice For the Prospective Attendee
To make the most of your Great Gotham Challenge experience, you’ll likely want to assemble a full team of four players. Ideally, you’ll want at least one team member who is relatively familiar with New York City since the city’s history and landmarks feature so heavily in the experience. You’ll also want at least one team member who is relatively comfortable with open-ended variety puzzles like Puzzled Pint. It might not hurt to recruit someone whose comfort zone is uncomfortable situations, because there’s almost definitely going to be at least one awkward conversation that someone will have to manage. It might also be worth tackling one of Great Gotham Challenge’s shorter games with your team, to get a feel for the event.

When it comes to the Flagship event, it’s generally better to secure earlier time slots, since the closing ceremonies happen at the same time for everyone and unless you’re confident in your solving or you’ve already played a few games, you’ll likely need the extra time. Those tickets go fast, so sign up for the mailing list now. Again you’d like to reach the end of the game, it’s also worth being fairly liberal in asking for nudges: for the June 8th game, only one team out of the 64 to finish made it to the end without asking for any hints.

The Great Gotham Challenge team has been fairly gracious about being flexible with players who want to keep playing after the closing ceremonies: this year, one team even completed the final challenge the following day since the final venue closed before they were able to get there. However, it’s best not to depend on that unless absolutely necessary.

Finally: if you find yourself worried about any of the things you think you’re supposed to do, contact GGC HQ to confirm. Recent games have done a good job of making it clear when you’re on the right track, but sometimes unexpected coincidences make the wrong track look awfully right, from a certain view.

Looking to Scratch the Itch? It’s More Than Just GGC:MMXXV
Great Gotham Challenge’s annual “Flagship” game is their primary public game, but the company offers slightly easier and more condensed events over the summer: Central Park Sprint focuses on Manhattan’s biggest park, while Terminal Time Trial centers around Grand Central Station. Instead of the Flagship’s 4-5 hour run time, these events are estimated to run around two hours.

The company also does custom events, including taking over as the designers for the annual charity puzzle event Compass, formerly known as Midnight Madness (as it was covered in the NYTimes a decade ago) with entry priced at a hefty $33,000 charitable donation for teams looking to participate.

As for the Flagship event itself: sign up for updates on the GGC website, and learn what surprises summer 2025 has in store for those brave enough to give it a try!