The Conundrum Box – Sleepy Hollow Part 3: The Headless Horseman

Kara’s Note: This review comes to you from me!

Location: Your Home!

Players:  We recommend 1-4

Price: $30 per box


From The Conundrum Box website:


This three part series takes place during American Revolution and afterwards. General Washington’s life is in danger! He has tasked you to help stop the most recent assassination plot. Your leads have led you to the small village of Sleepy Hollow where you meet the townsfolk, and soon discover their dark secrets. The second and third adventures in this season get weirder and darker.

First Impressions:

As the last box in the Sleepy Hollow series, I was excited to see how the story would end. Given the interesting twist and cliff-hanger of Part 2, there’s no telling where this one would lead!

Yay Points:

The story drops you in the middle of a predicament, and it’s not long before you’re able to escape and get some clarity on the situation. You are soon tasked with multiple sub-goals to help you toward your larger goal, and fortunately, you’re provided with a document to keep track of each one you’ve achieved. This is immensely helpful since this box is jam-packed (in a good way!) with puzzles of varying difficulty levels and a lot of satisfying solves.

The clues interacted with each other in many interesting ways. In particular, there was one set of deceivingly simple clues that played a helpful role in a couple of the puzzles, and we really enjoyed deciphering them. We had some good lightbulb moments when making connections, and also some ‘ohhhh’ moments when catching ourselves overthinking. On a potentially unrelated note, if you’re like us, please remember to look on the front and back of everything. 😀

It was pretty clear what we needed from Parts 1 and 2 to help us solve some of the puzzles, with a lot of good callbacks to them. (Side note: Though it’s taken me 3 boxes to finally learn, I will also be a little better at notetaking when I make a solve or notice something in a box series that doesn’t seem to be used in the current box.) I also really liked how one set of clues built upon a prop from a previous box to make for a new interaction, and more tactile players will benefit by having another figure to help you visualize this puzzle.

In the previous box, I noted how one of the color puzzles was tricky as I had a hard time telling some of the colors apart. I’m happy to report that it wasn’t an issue in this box!

As with all The Conundrum boxes, we really appreciate the incremental hint system that the website provides. It’s really helpful in making sure you’re on the right track, and also helps you figure out how solve it so you can learn and understand the process.

Pondering Points:

While my husband and I both agreed that this box started and ended great, the middle can be a little rough for players who don’t enjoy longer process puzzles. (Editor’s Note: Special thanks to Kara for having much more patience than I for process puzzles. My disdain for them has been well documented.) One of the puzzles involved a challenge that I found satisfying to solve, but can definitely be an exhausting experience for many players to repeat the process so many times (especially since even if you know what to do, it’s not always an easy find).

There was also one puzzle that I really relied on the hint system to help fill in the blanks on what I need to do with it to make the solve. I may have missed it, but perhaps a little more direction in the puzzle would be helpful.

We liked how one puzzle gave us an easy/hard option to choose from. However, we were a little disappointed when we found out that none of our possible solutions to the hard puzzle worked because one of the clues seemed to contradict the accepted answer (though, giving a shout-out to the hint system for instant-gratification to help us figure this out). This should hopefully be an easy fix, though.


This box had a lot of great puzzles that were fun to solve, though there were a couple longer ones that may be a hit or miss with players. It certainly was an interesting end to the series, and provided a surprising foreshadowing of a future box. Subscribe to The Conundrum Box here! You can get $5 off your first box with our Promo Code ERA5OFF!

7/10 (Good)

Full Disclosure: The Conundrum Box provided a complementary review copy.


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