I've been doing some thinking about the types of adventures I'd love to go on, and I happened to recall one of my favorite things I've recently done. I didn't intend to do many retrospectives here when I started; I'd rather look forward instead, but I feel like this was cool enough for me to make an exception. So what exactly was it? Essentially, I designed, planned, and then competed in a big scavenger hunt all over downtown Toronto which I found to be one of the most fulfilling activities I'd ever done.

So firstly, a little background. I conceived of this when I was trying to come up with something that combined all of my favorite kinds of activities. I love cities, and traversing them in many different ways (whether that be by bike, on foot, with transit, or more). I'm somewhat competitive, and wanted a (preferably meaningless) challenge that let me compete against my friends. I enjoy excuses to exercise my creativity, and it would be great if I this challenge encourages brainstorming unique and obscure ways to complete it. I'd spent a long time with these ideas at the back of my mind, but they never crystallized into anything concrete; just a vague urge to race my friends sometimes or to vault fences for no reason. That was until I started putting the dots together and figured out exactly what I was looking for.

The Design of the Hunt

I was inspired to do this by traditional scavenger hunts, but I felt they lacked something. It's fun to go around and try to spot a specific leaf or funny hat but these items often feel arbitrary; they require more luck than actual skill to track down. Additionally, since I was leaving Toronto around that time I wanted to do something that really tested and rewarded knowledge of the city. I looked online but many of these seemed more aimed at tourists, showcasing attractions over testing actual knowledge of the city (I didn't want to just visit the CN Tower, City Hall, and the AGO). And frantically racing from landmark to landmark just to take a photo with it seemed a bit simplistic - where's the fun in that!

On a random weekday evening I just started writing down challenges that sounded much more interesting to me, and sharing these ideas with my friends. At this point I had no serious plans to put something together, but sometimes just putting an idea into the world gives it a life of its own. By now I couldn't stop; the list of challenges just kept growing. It seemed I'd have little choice but to actually run the scavenger hunt. Some of my friends also helped pitch in with some challenge ideas as well so credit goes to them for helping to flesh out this exciting idea.

So what did I do differently compared to the other scavenger hunts I just described? First of all I tried to think of challenges that encouraged exploring and interacting with the city. For example, "reach the tallest point you can get to at U of T" (luckily many of us were current or former students) or "pose interacting with a mural" were two fun challenges that got you to think about places you'd visited as a student or recall interesting city artwork you might have walked past otherwise. Secondly, I tried not to require specific locations for the challenges so multiple teams could complete them in different ways. For example, challenges like "Build or find a sand castle" or "stack 5 rocks on top of each other" aren't very complicated but each team will have a fun and unique story about what they did. Finally, and my favorite part, was setting challenges up so some teams could complete them better than others; each challenge would become its own mini competition. "Walk the PATH (Toronto's underground tunnel system) for as long as you can" and "get off a streetcar, and run to the next stop on foot before it arrives" were fun because you don't know exactly how well the other team will do, or whether they'll attempt the challenge at all, so in doing it you need to balance between doing it well and not spending too much time on it. I'm pretty competitive so these were my favorite.

One thing I'm happy about is the fact that we came up with so many challenges that no one team could hope to do them all. This gave each team their own story and path they took around the city, which was fun to share at the end when we all compared each of our journeys. Because challenges could be completed differently and had different difficulties, we needed an impartial judge to review and score everything; this ended up working quite well as they also contributed a handful of riddles to solve which added to the adventure. I'm also happy that we were able to stick to a minimum of rules to let teams have the maximum amount of freedom. The main one was that teams must stick together; we also banned driving but I think driving wouldn't have given much of a benefit anyways since it was going on in dense downtown (as it should be in a well designed game). If you're interested in running something like this for yourself, here's a handful of other :logistics.

Some other challenges I am quite fond of:

• "Purchase bubble teas from at least 3 different stores to create a rainbow of colors"; this was kind of an easier challenge meant to give everyone a breather and let everyone get a yummy drink. Unsurprisingly every team ended up doing it! It was also fun to see what flavors everyone picked for their three colors.
• "Have one angry coach teammate yell at the others while they do push ups in a kids’ playground"; again not the most difficult challenge, but the videos of this were very funny to watch.
• "Fly a kite"; this one is fun because it has a lot of moving parts. You need to find a store where kites are sold, take it to a wide open area, assemble it, pray for wind, and actually fly the thing. Plus, I do kind of love kites.
• "Have a discussion with the anti-lockdown people at Queen’s Park"; the protests were going on around this time, so how could we not include them! Plus the people there were quite interesting to meet, and it definitely left me with a unique story.
• "Pour lake water into Nathan Phillips Square fountain"; this one is surprisingly tricky. It was fun figuring out how to get the lake water and how to quickly and safely transport it all the way to city center. It was also the excuse I needed to convince my team to use bikeshare, (we wouldn't have made it on time otherwise).
• "Record a rap video with the CN Tower in the background"; two of the teams actually used the exact same Eminem song to complete this! It was pretty funny when we realized.

:x Logistics

We luckily ended up with 9 of us interested so we separated into 3 teams of 3. However I don't think uneven teams are necessarily worse so I don't think it would be a huge issue otherwise. We required each challenge completion to be recorded with a photo or video; half the fun was reviewing everybody's pictures and hearing the story behind them when we finished. We all met in one place to get started, and gave ourselves 3 hours for the game including getting back to the starting location. This felt like a huge amount of time before we started, but in retrospect it was pretty ideal. Personally I wouldn't have minded an even longer game but at this point I think lots of us were getting tired. With 3 hours I think we only ended up using about half of the forty total challenges (and one riddle) but having a diversity of challenges was really fun. If driving would confer a significant and unequal advantage, then banning driving makes sense. The other important rule is that teams must stick together at all times, otherwise it might as well be an individual game.

My Inspiration

It wouldn't be fair of me to pretend I came with all of this entirely on my own. I definitely had my fair share of inspirations coming up with this, and I hope to continue to be inspired to do more exciting city challenges and to inspire others to try it as well. My first big inspiration was from this :Tom Scott video. The format isn't exactly the same, but seeing Tom run through London trying to do challenges kind of awakened a spark in me; I realized how much fun running through a city could be. Since then he's made two more videos of a similar format, all of which I love the idea of. They were released after I had my scavenger hunt, but they gave me tons of new ideas which I'll get to below.

A much bigger inspiration of mine has been the games developed by the hilarious people at the Jet Lag youtube channel. They come up with travel based games like circumnavigating the globe or playing connect 4 with US states, which are of course filled with challenges the players must complete at various locations. Seeing these videos a few days before I planned my event is probably what inspired me to come up with challenges that one evening, especially because I found their challenges so fun and unique. I could talk about Jet Lag all day and how cool they are but I don't wa- actually, you know what? :Maybe I will.

:x Jet Lag

I'd like to go into a little more detail about each of their three challenges so far and why I like them. They also have a new series with a fourth challenge releasing soon that I'm very excited about.

The first game they played was connect 4 with US States. Essentially you had to travel to one of the allowed states (only western US since the states are more regular) and do a challenge at the state capital to "claim" the state. The states could only be claimed once, and the first team that could draw a straight line through 4 connected and claimed states won.

I was really inspired by this challenge, and it's probably still my favorite. I hope to one day do this game myself with a group of willing friends, although it's quite rough to travel so much so I suspect most wouldn't be interested. I like it because there's a surprising amount of strategy in picking states and blocking the other team, the US is a pretty fun place to travel and traversal is not too difficult, and most flights aren't too long. This is definitely something I'd be interested in organizing, and if you think you'd like to play please send me a message or something, it sounds super fun.

Their next series was racing to circumnavigate the globe, requiring challenges to be done to get coins to pay for flights. This wasn't as fun in my opinion because there wasn't as much interaction between teams - no blocking off states or anything. Plus, the trans-continental, double digit hour flights can be very grueling so I wouldn't want to repeat that. One cool part is that they visited much more exotic locales around the world like Singapore and Amsterdam.

Their latest was playing tag across Europe, with a runner trying to reach a specific point while doing challenges being chased by chasers who know the runner's location. This was cool since it had a lot of player interaction, tons of mind games and tricks, and Europe is pretty easy to get around via train. Being able to visit so many countries was fun as well. I'd definitely like to try this at some point to but I unfortunately have much less friends in Europe. However I am considering adapting it to work in a different area...

One of my favorite parts about these series is the challenge design. They require interacting with the location they're in (of which they visit many) in a much more interesting way than just visiting the top tourist attractions. Things like "Paint a Local Landscape", Visit the US Consulate (without using your phone)", "Estimate Your City’s Population", or "Attend the entirety of a local sporting event". I feel like doing these random things in cities (especially which being chased) is such a cool way to experience travel.

What's Next

After putting in all this work to design and execute this amazing adventure, I simply can't let it be my magnum opus. Surely I'll have to top this somehow, right? As usual, the biggest obstacle to stuff like this is organizing the time and people to come together and do it. A 3 hour challenge in one city is not too bad, but trying to do it for longer or in a place where I know less people would be much harder. To that regard, if you're reading this and you like me enough to team up or compete against me to complete challenges while running around please let me know. I'll happily take anyone who has that same spark as I do when it comes to games like this.

I've also brainstormed a lot about ways to make smaller scale and more accessible city exploration games that only require 2 or 3 people. For example, one player could attempt to accomplish tasks, another might be chasing them, and a third would see the location of both places and be in charge of directing the second player over the phone. I think something like this offers lots of potential for strategic thinking and counterplay, which still incentivizing interacting with the city in interesting ways (depending on the challenges).

When you want something that doesn't yet exist, I think it's your responsibility to go out and create it. To bring it forth using your creativity and sheer will. That is sometimes possible to do alone, but all of the greatest works necessitate collaboration with others. I don't know how successful this and future experiments will be, but I surely intend to do my best to accomplish them.