The Great Gotham Challenge

A few decades ago, I lived in New York City, and every once in a while I would hear about some puzzle-adjacent event taking place. Maybe it was in a museum, maybe it was an exploration of one neighborhood or another. We would form teams and walk around (in one memorable instance, we were driven around in a limousine), and we would look for clues, each of which would lead to the next location and the next clue, until you eventually reached the finish line. A fun idea in theory, but none of these events were executed particularly well — they were all lackluster at best, and several were worse than that.

Thirty years later, I have finally had the experience I hoped for all those earlier times, for I have now participated in the Great Gotham Challenge. I flat-out would not have considered schlepping down to the city for this, but I was given a comp by the event’s co-creator, Theresa Piazza, and I am extremely grateful for her generosity.

I assembled a team of local puzzle friends (shoutout to Jon Delfin, Jeffrey Schwartz, and Francis Heaney), and together we met at the event’s starting line, just outside of Moynihan Train Hall. Bunches of teams would be heading off from this spot at various start times over the course of the day — at our 1:00 p.m. start time, there were ten or a dozen such teams ready to go. There were a few rules and introductions that needed to happen, and these were delivered by a trio of people wearing, for some reason, vaguely military or science-fictiony jumpsuits.

The event didn’t seem to have a theme beyond “let’s explore New York City.” No matter. Give me some good puzzles and an interesting experience, and I’m yours. And the Great Gotham Challenge provided this to near perfection. Over the course of four hours, my teammates and I solved a dozen puzzles across a wide swath of Manhattan, and I lost count of how many times I said “What?!?” and “Wow!”

Since the Challenge is over, I asked for permission to turn the Spoilers knob up to 11. Permission received. And so let’s take a deep dive and look at a puzzle event done right, with solid puzzles consistently executed with panache.

Puzzle 1 – The Envelope: We started with a large envelope, in which there was a card with a verse on it, and some random-seeming numbers on the opposite side. We used the numbers to pull a hidden message out of the verse, and one of my teammates saw how to use that message with the details on the envelope — the fake postmark and the fake cancelled stamp. Pretty good, and just the right amount of tricky. While this was an impressive start, I jumped to the conclusion that every puzzle would be much the same: Here’s an envelope. There’s something inside it. Solve it.

This conclusion was wildly incorrect, as we shall soon see.

Puzzle 2 – Making Connections: We were next sent into Moynihan Hall itself, where we were told to make contact with — which is to say, literally shake hands with — ten or so people wandering around. Wait a minute, I thought. This is only the second puzzle, and it involves TEN actors? I was starting to think this event might be more ambitious than I originally assumed.

We were given descriptions of the ten people, but finding them all was far from trivial. The “influencer” was pretty plain, standing there with a phone attached to a selfie stick and a ring light, flipping her hair and putting on a show of being ostentatious. But others were far more subtle. The hint about “rolling purple” — did that indicate the otherwise unremarkable guy with the purple suitcase? What about the person who, we were told, had pulled an all-nighter at NYU? If we wanted somebody who looked tired, there was a wide assortment to choose from. We absolutely did not want to approach anyone not involved in our game.

Ultimately we made all of the right choices, shook hands with everyone, and with each interaction, received small cards with words or phrases on them. These, it turned out, fittingly made a slight variant on a New York Times “Connections” board, the solving of which resulted in the answer we needed to continue.

Puzzle 3 – The Printout: We were sent to a Fedex/Kinko’s to print something out. We made our request to the guy behind the counter, who had no idea what we were talking about. (If he was playing dumb, he played his role superbly.) When we finally revealed that we had a “retrieval code,” he directed us to a copier where we could plug that in, but that machine seemed to want us to set up an account with a minimum of $5.00. Surely that wasn’t something the gamerunners expected of us, right? We stood there dithering, to the attendant’s rapidly increasing exasperation. “That is a retrieval code,” he said. “I have worked here for three years. I know what a retrieval code looks like. You type it in there.“

Finally, he went behind the counter and typed in the code on his own computer. “See, it works,” he said, although we could not see because only he could see the screen. Could he print that out for us? He could, and did, at a far more reasonable cost of 44 cents, and we finally had our puzzle: A bunch of rebuses on New York City neighborhoods, which we made short work of, and which led to a surprisingly elegant extraction that used certain rebus elements a second time.

Puzzle 4 – Popsicles: My team got a little lost en route to the next puzzle station, which was on the High Line, the long, elevated public park built into a former freight line. We couldn’t seem to find a vendor selling Mexican ices. We asked at the Information booth, and they said there was nothing like that here, which was in one sense absolutely correct — nobody was selling ices. But about a hundred feet away and FULLY IN VIEW OF THE INFORMATION BOOTH was a fellow giving away ices if you knew to approach him, and knew to tell him a knock-knock joke. It took us longer than I care to admit to make contact with this guy and get our popsicles, but they were a nice little treat when we finally got them, and it was pretty nifty to find the next puzzle on the popsicle sticks.

Puzzle 5 – Portal to Another World: No, seriously, that’s what we were told to look for, somewhere on a largely empty street in Chelsea. How does an actual, non-fictional person find a portal to another world? We walked around the designated area for a while, asking ourselves this question. And finally, our eyes were drawn to a truck parked nearby, it’s back door fully open to reveal a floor-to-ceiling heap of boxes.

What was that in the lower corner? That box is open, and seemed to lead to some sort of tunnel. My teammate Francis jumped into the truck and crawled down the tunnel, and sure enough… well, it was not, to be honest, a literal portal to another world, but it was a delightfully theatrical way of giving us the next puzzle, in the form of a UPS envelope.

Puzzle 6 – Twist and Turn: And here we ran into one of the only flaws in event’s design. In the back of the truck, as Francis was given the envelope that contained this puzzle, he was also given — several times, with clear importance — a particular phrase. We tried to figure out how to apply that phrase to the contents of the envelope, a clever paper sculpture in three sections that could be twisted and turned in various ways to form the head, torso, and legs of an assortment of people. Presumably if we understood how to use that keyphrase, it would give us an insight into the proper orientation of this sculpture. We twisted, we turned, we thought, we spun our wheels, and then finally we took our first and only hint, where we learned that what Francis was told in the back of the truck was itself an answer that was supposed to be submitted, and it had nothing whatsoever to do with the sculpture.

So we submitted the answer, and it unlocked a whole lot of information necessary for solving the sculpture puzzle, which we then did in less than two minutes.

Puzzle 7 – Window Cleaner: Back on the High Line, we were given clues that led us to a fake ad for a window cleaner. We called the phone number, and followed the recorded directions, which was a simple enough thing to do seeing as the High Line is a narrow straight line cutting through Chelsea. Eventually we wound up at a particular park bench where we found…

Puzzle 8 – The Overlay: We retrieved an envelope in which was a single sheet of acetate. In the upper left corner was a very specific set of coordinates. The rest of the sheet was taken up with a set of lines of varying thicknesses, arrayed so that it resembled a street scene — a crosswalk was easily recognizable, and some bike lanes. Okay. There were also some letters peppered throughout the scene. We found a view of the street that seemed to match what was depicted in the overlay. But now what?

The very specific coordinates pointed to the street level below the High Line, and unfortunately my teammates took my advice and we descended from exactly where we needed to be to solve the puzzle. After a little bit of flailing around, we returned to the High Line and our view of the street. (I was starting to get well and truly tired of going up and down stairs.) We tried to line up the overlay precisely with the street scene, though it was hard to say exactly what that would have accomplished.

“Am I crazy,” I said, “or is there an O in the crosswalk down there, just as there’s an O in the overlay?”

Light bulbs went on over all four of our heads. “That’s not an O in the crosswalk, it’s just a circle. And there’s another circle…”

“And there’s another one…”

“And another.” The circles painted on the street corresponded to the letters on the overlay, and reading only those letters got us our answer. Unexpected and delightful.

Puzzle 9 – The T-shirt: We’re directed to a particular laundromat, where the Chinese woman up front winks at us because it’s plain as day that we are not here to do laundry. In the rearmost dryer are a jumble of white T-shirts. We take one, as directed. It shows a line drawing of a building, and a hand holding a key, and a bunch of abstract shapes. Presumably it is also a puzzle, although I don’t yet understand how that might be.

As requested, we leave the laundromat, and the instant we step outside, the T-shirt’s drawing floods with color. It’s made with photochromic dyes that change in direct sunlight. We take it to a nearby park, sit in the sun, and solve it.

Puzzle 10 – Fashion Posters: We’re told to look across the street from a hardware store, but it’s not at all clear what we are looking for. I stare at a list of special drinks on a blackboard outside a restaurant, willing it to become a puzzle. It does not cooperate. Something on the sidewalk? These posters on one of the boarded up buildings?

Holy crap. At a glance, the posters are for some fashion company or another, model looking off into the distance, posing against a white background. At a second glance, the woman is wearing the vaguely military or science-fictiony jumpsuit that the gamerunners were wearing back at kickoff. The posters are riddled with Ben-Day dots, like a comic book viewed in extreme close-up. I try treating these like a Magic Eye, which turns out not to be correct, but after staring long enough I thought I could discern the shapes of letters. Ultimately, Francis had the excellent idea of taking a picture of the posters and playing with the color saturation levels. That did the trick.

Puzzle 11 – Perfume: At the end of the High Line is a food court and marketplace. One of the booths is for the same fictional fashion company depicted in the posters. This must be the place.

The company has a line of perfumes to go with its cutting-edge jumpsuit fashions. We are given a small box of samples, and a card with marketing text on one side and a grid of letters on the other. Along the top and sides of the grid are the names of possible scents. Uh-oh. I have encountered olfactory puzzles in escape rooms, and it turns out I am not very good at identifying single scents. Now it appears that we will need to identify two smells in combination.

One smell is always the dominant one, but luckily my teammates do not always agree on which smell is stronger. We circle letters in the grid with varying levels of confidence. Finally, we rely on the fact that every single answer has had a strong thematic connection to its puzzle. That plus our pool of maybe right, maybe wrong letters is enough to get us to the finish line.

Puzzle 12 – Boba Tea: At a particular store in the Chelsea Market, we are given boba tea in plastic cups specially printed for this event. The cups, when nested into each other and oriented correctly, reveal Braille letters. I call up a Braille table on my iPad, we watch Francis do the decoding, and suddenly the event is over. We are invited to a rooftop lounge to confirm our final time and to mingle with the other teams. Ta-da!

When my team of puzzle constructors were first setting off to make the 2022 Mystery Hunt, we brainstormed a list of adjectives we hoped that solvers would apply to our event. One of these was wonder. We wanted to deliver a sense of wonder — not consistently from start to finish, certainly, but in special little moments here and there. This was a bit of a tough go considering that we were forced to hold our event virtually, but I still think we managed it in a few places.

Wonder is an excellent thing to shoot for in a puzzle event. Anybody can hand out a bunch of crosswords or other word puzzles. I’ve done it myself. But if you are running a day-long or weekend-long event, you are implicitly promising something epic. That’s a tough thing to deliver.

Well, the Great Gotham Challenge delivers. My jaw dropped when I realized the portal to another world was in the back of that innocent-looking truck. I was staggered all over again when I stopped looking past those fashion posters and started looking at them. And how many specially created objects did we encounter during this event? The popsicles, the boba tea, the color-changing T-shirt, the perfumes, the paper pop-up sculpture… good heavens, that’s a lot.

I have my nits — I’ve been nerding out on puzzles for far too long not to have them. It would have been nice to have some idea of where we were in the event’s path — somewhere in the middle? Close to the end? As we kept walking, with increasing tiredness, from puzzle to puzzle, some indication of our progress would have been appreciated. I didn’t know the boba tea puzzle was the finale until we had finished it.

Relatedly, while I have played several excellent puzzle events with no metapuzzle — the reuse of the previous answers in a sort of grand finale — I always mentally dock a couple of points when a metapuzzle is absent. A puzzle hunt is a kind of story. When telling a story, you want to find a way to deliver a socko ending. A metapuzzle is a time-tested way of doing that. The GGC just kind of stops.

But these are quibbles. I went into this not really knowing what to expect, and came away dazzled. I think back to the painful look-for-the-clue games I played in New York City thirty years ago, and I want to zip back in time and tell my younger self, just you wait. The really good stuff is on its way. I won’t need a comp next year. I’ll buy a ticket at the first opportunity.