Pleasantville Puzzle Hunt

02/06/2026

It's gonna be a cold this weekend. So if you didn't do the Hunt yet, try it indoors!

Go to https://spaces.hightail.com/space/tOOStiWUQm on your computer (NOT MOBILE DEVICE).

Download and print the Puzzle Pack.
Download but only print the last 2 pages of the Interactive Location Pack.
When you're done, the Answer Pack is there, too.

Stay warm, Hunters!

Hightail Spaces lets you send unlimited files, of any size, to anyone. Collaborate with your team and evolve your work.

11/30/2025

Hi everybody, thanks for another great Pleasantville Puzzle Hunt.

TLDR: THANKS, WINNERS, ANSWERS, AND HOW TO STILL PLAY IF YOU MISSED IT.

FIRST, THANKS!

Kat, Greg, Whitney, and I would like to the Village of Pleasantville, especially Mayor Peter Scherer and the Recreation Department for their support.

Thanks to Sir Speedy for generously donating the printing, to the Pleasantville Farmer’s Market (and the Nemec family!) for generously donating prizes, and to H Plus for printing the clue at the Little Free Library.

Special thanks also to Dolphin South, Pleasantville Children’s Center, Super Awesome Artland, and The Don Juan for their participation. And thanks to all of you for making the Hunt such a fun annual event!

Randomly picked WINNERS for 2025 are Stephanie and Chase Casper, Tara Albaum, Julia Cowitt, Stephanie Servetz, Kent and Mark Almassy, Rachel Parsons, Sheila Cravetz, Katie, Nick and Matty Wisz, Helen Meurer & Paul Loring, and Marise Butterly and crew. Please pick up your prize after NOON on Tuesday 12/2 at the Pleasantville Recreation Center on Marble Avenue.

There were 37 correct answers submitted this year. And there were some stumpers out there! You know which puzzles and locations we’re talking about!

WANT TO TAKE A PEEK AT THE ANSWERS?

The Answer Pack is now on our Hightail Space. Remember to access it on a computer, NOT a mobile device.

https://spaces.hightail.com/space/tOOStiWUQm

It will have explanations of all the answers. Including those big stumpers.

MISSED THE HUNT? YOU CAN STILL PLAY!

Also on our Hightail Space is an Interactive Location Pack.

https://spaces.hightail.com/space/tOOStiWUQm

HERE’S HOW IT WORKS:

ON A COMPUTER, ***NOT*** A MOBILE DEVICE:
1. Download and print the Puzzle Pack. Solve it as usual.
2. Download the entire Interactive Location, but ONLY PRINT THE LAST 2 PAGES. Keep everything else electronic. The interactive part contains a map of Pleasantville with links to photos of all the locations and clues. The printed pages will sub in for certain things you would have needed to do at the locations.
3. Work back and forth between the printed Puzzle Pack and the Interactive Location Pack.
4. No peeking at the Answer Pack! That is, until you’re finished. Happy hunting!

Remember to share your experience with friends and ask them to like this FB page for updates. And if you have photos that you don’t mind if we use, we’d love to see them as well! Send all of it to us at [email protected].

Until next year,
Andy, Greg, Kat, and Whitney

Hightail Spaces lets you send unlimited files, of any size, to anyone. Collaborate with your team and evolve your work.

11/30/2025

ANSWERS IN BY 4:30. Good morning! A friendly reminder that Pleasantville Puzzle Hunt entries need to be in by 4:30 pm today to be eligible for a randomly drawn prize. Rain is predicted to begin at noon, so vroom vroom! Also, once you submit, check your email. You will get an auto reply but also a personal response of whether you got it right or need to resubmit. If you need to resubmit, get it in by 4:30. Thanks!

11/29/2025

WHERE IS THE CLUE? Each of the 8 preliminary puzzles leads you to a location, and MOST locations have a traditional clue and/or instructions. One doesn’t! WHY? Because everything you need to solve the puzzle is at the location and in the puzzle itself. Where is it leading you? What are you looking for? What specifically? (Hint: It’s not a single hidden shape within a shape. Bonus hint: think of where you are—what that building is!) But remember—once you find what you’re looking for, that’s not the answer. You’ll need to use that information to discover the answer on the puzzle page!

Send a message to learn more

11/29/2025

IT’S SMALL BUSINESS SATURDAY. While you’re hunting for clues around the village, stop in at the local shops and hunt for gifts!

11/28/2025

BOOM! The 2025 Pleasantville Puzzle Hunt is ready for downloading. Or... pick up a printed copy at the Pleasantville Recreation Center (mailbox) on Marble Avenue. ENJOY.
https://spaces.hightail.com/space/tOOStiWUQm
FOR BEST RESULTS, OPEN ON A COMPUTER, NOT ON YOUR PHONE. TRY COPY AND PASTING LINK into browser if you are having trouble downloading packet.

Send a message to learn more

11/24/2025

GET YOUR PENCILS READY....
The Pleasantville Puzzle Hunt 2025 starts this Friday at 10am. A super fun group activity that gets you thinking and moving! Win win.

Friday, November 28th, 10am — Sunday, November 30th, 4:30pm
FREE fun for all!

What is the Pleasantville Puzzle Hunt?
The Pleasantville Puzzle Hunt is part brain games, part scavenger hunt, and a great way for families, friends, and neighbors to explore our village. Solve pencil puzzles in the Puzzle Pack for clues to secret locations around the village where you’ll find even more clues toward a final Metapuzzle. Finish the Puzzle Pack and submit your final answer by the deadline for a chance to win a prize!

How to get the puzzle packet:
Starting Friday, 11/28, at 10am (and not before!): Visit the Pleasantville Puzzle Hunt page on Facebook or email [email protected] for a link to the downloadable Puzzle Pack.
A limited number of printed Puzzle Packs will be also available in the Recreation Center mailbox beginning Friday 11/28 at 10am.

For Updates and Information:
Follow Pleasantville Puzzle Hunt on Facebook or Instagram and watch for community emails.

11/17/2025

We’re so excited for this year’s Pleasantville Puzzle Hunt! It all starts Friday, November 28 at 10am. Thanks to Village of Pleasantville, New York for the shout-out!

11/15/2025

IT'S HUNTING SEASON! The Chamber of Commerce has a Wicked-themed scavenger hunt. So does the Library! And of course, completely separate, starting November 28 at 10am, we have THE 6TH ANNUAL PLEASANTVILLE PUZZLE HUNT. Sharpen your pencils. Gather your teams. See you around the village!

Send a message to learn more

11/15/2025

IT'S HUNTING SEASON! The Chamber of Commerce has a Wicked-themed scavenger hunt. So does the Library! And of course, completely separate, we have THE 6TH ANNUAL PLEASANTVILLE PUZZLE HUNT. Pencil puzzles, clue hunting, and a tour of Pleasantville with friends and family. Puzzles are all written and ready to go, and we can't wait to share it with you. It all starts Friday, November 28 after 10am.

Send a message to learn more

12/01/2024

ANOTHER PLEASANTVILLE PUZZLE HUNT IS IN THE BOOKS.

A NOTE OF THANKS, WINNERS, ANSWERS, AND HOW TO STILL PLAY IF YOU MISSED IT.

FIRST, THANKS!
We’d like to thank the Village of Pleasantville, especially Peter Scherer and the Recreation Department, for their support. Special thanks also to Second Mouse Cheese Shop, Little Crepe Street/Little Mumbai Market, and Lucy’s. Thanks to The Examiner, Pleasantville Press, and all of you for spreading the word and making the Hunt such a fun event!

Randomly picked WINNERS for 2024 are Stephanie Ells, DeWitt Sullivan, Isabella Dean, Alex Kuo, and Kathy Herron & Caroline Scherer. Please pick up your prize after NOON on Tuesday 12/3 at the Pleasantville Recreation Center on Marble Avenue.

There were 45 correct answers submitted this year. That is beyond awesome!

WANT TO TAKE A PEEK AT THE ANSWERS?
The Answer Pack is now on our Hightail Space. Remember to access it on a computer, NOT a mobile device.
https://spaces.hightail.com/space/yHoP9kI8k0

MISSED THE HUNT? YOU CAN STILL PLAY!
Also on our Hightail Space is an Interactive Location Pack.
https://spaces.hightail.com/space/yHoP9kI8k0

HERE’S HOW IT WORKS:
ON A COMPUTER, ***NOT*** A MOBILE DEVICE:
1. Download and print the Puzzle Pack. Solve it as usual.
2. Download but DO NOT PRINT the Interactive Location. It contains a map of Pleasantville with links to photos of all the locations and clues.
3. Work back and forth between the printed Puzzle Pack and the Interactive Location Pack.
4. No peeking at the Answer Pack! That is, until you’re finished. Happy hunting!

Remember to share your experience with friends and ask them to like this FB page for updates. And if you have photos that you don’t mind if we use, we’d love to see them as well! Send all of it to us at [email protected].

Until next year,
Andy, Greg, Kat, and Whitney

12/01/2024

Hi everybody! A reminder that the official Hunt closes at 4:30 pm today. Get your answers in by then for a chance at a prize. Answer Pack will be posted at 5:00.

Send a message to learn more