ACTIVE THROUGH FEBRUARY 20th, 2026

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.

• You have exactly one week to solve each puzzle. After each puzzle's deadline, you may access a hint here and continue solving, but you’ll no longer be eligible to win anything other than the prize card.

• IMPORTANT: enter solutions in ALL CAPS, and remember that finding the password entry page may be part of the puzzle.

• Once you’ve solved each puzzle, a webpage will prompt you to enter your info. This timestamps and records your successful completion.

• Solve at least three puzzles to win The Winter Challenge prize card. Solve all six for a chance to win additional prizes! Rankings are determined by average solve speed across all six weeks.

• 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. Get in a practice round with previous Winter Challenges!

Time to complete:
The whole Challenge lasts six weeks; the time required to solve each puzzle varies. You won’t 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 pick it apart, come back to it later, or do a little internet sleuthing. 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.

Prizes:
The prize pool varies from year to year, but often includes Philly street art, Philly photo prints, gifts from sponsors, and creative works donated by fans. 2026 is the first time I’m creating a Winter Challenge prize card! Solve at least three puzzles to earn yours and add it to your collection.

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 Aviz! If you’d like to donate prizes, please reach out.

Thank you also to Otherworld Philadelphia for providing prizes to The Winter Challenge 2025!

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