RETURNING WINTER 2025

Need a puzzle fix right now? Get into the right headspace by downloading the first Winter Challenge!

Each winter, to help my Puzzlers get through the colder months, I create a completely original series of six increasingly challenging puzzles and send them to my email list. Here’s how it works:

• Each Friday at 6pm EST, I send an email containing a puzzle you can solve from anywhere in the world.

• You have exactly one week to solve each puzzle. After each puzzle's deadline, you may access a hint here and continue solving, but at that point, you will no longer be eligible for one of the grand prizes.

• IMPORTANT: solutions are single words, which must be entered in ALL CAPS.

• Once you’ve solved each puzzle, a webpage will prompt you to enter your Instagram handle (or email address). This timestamps and records your successful completion.

• If you solve all six puzzles (within that one-week timeframe for each one), you’ll win a prize at the end!

• You can start or stop at any time—there’s no commitment or obligation. Just have some fun solving some unusual puzzles!

Where:
In your inbox.

When:
Each winter.

Time to complete:
The whole Challenge lasts six weeks; the time required to solve each puzzle varies. You will not have to spend hours decrypting a cipher with brute force or anything like that. But some of the puzzles may take some time, because they require some outside-the-box lateral thinking. Sometimes you’ll “get it” and sometimes you’ll have to stare at it for a while or come back to it later. If you get frustrated, try a different approach. Remember, it’s meant to be challenging—it’s not called “The Winter Walk In The Park!”

Difficulty:
◉◉◉◉◎

Price:
Free! If you really enjoy yourself, I always appreciate tips.

How to participate:
Just join The Puzzle Well (my email list) at any time and you’ll start getting puzzles when The Winter Challenge begins.

Many thanks to artists who have donated prizes to The Winter Challenge:
Carole Loeffler, Garbage Grease, The 666 Cat, ManyFriendss, PHL Tile Research Institute, Gloopy Goblin, Yerp, and more to come! If you’re an artist who’d like to donate prizes, please DM me on Instagram.

Note: the puzzle pictured on the homepage is from the first Winter Challenge. It is not related to any currently running puzzles.