Give your teachers and staff a holiday appreciation week they’ll remember forever.

What is it?

In a world of AI and 24/7 screens, Old School Holiday turns any week in December back into a time before tech headaches by playing a game in the background of the week based off all the holiday traditions that brought us together in the past.

As your week progresses from modern traditions to the downright ancient, everything builds from laughter to nostalgia, from nostalgia to gratitude, and from gratitude to genuine connection and camaraderie as you head into 2027.

How much?

FLASH SALE: $69/school ($109 after November 5th)

Automatically go to download page after ordering.

100% Satisfaction Guarantee - Love it or email us to exchange or refund.

Includes 24/7 customer support to walk you through everything and answer questions.

What is the game like?

The week begins with a humorous kickoff email (email is old-school, right?) detailing how you’ve been looking for a way to thank your staff for all their hard work in 2026. You’ve found a game where schools participate in a big list of holiday traditions with a twist, and you’ve decided to take it on to help entertain everyone as you head into the break.

Though it’s a game, there’s no pressure, no competition, and no added time requirements on their busy schedules.

The goal is to simply enjoy the week, and staff earn “Merriment Tickets” with each activity they play. The tickets create several opportunities for “Let’s Make a Deal” type fun, bargaining with the Yule Goat (yes you read that right), and even a chance to win an actual trip to Tahiti (because nothing says “recovering from the holidays in style” like relaxing thin the South Pacific)

Each day represents a new era of holiday traditions taking you all the way back to ancient times. Examples include:

• Elf on a Shelf

• Hot Chocolate Bar

• Festivus

• Ugly Sweaters

• Cookie Decorating

• Wassailing

• Modern Caroling

• Greeting Cards

• Yule Goat

• Lord of Misrule

• Ancient Caroling

• Mistletoe Hunt

• And the Lantern Walk of Good Tidings

Some moments are quick and silly, others unexpectedly meaningful, and together they turn an otherwise exhausting final week into something everyone can genuinely enjoy.

Everything is laid out to keep things EASY on you. Just follow the suggested week and pre-written emails and then watch the fun unfold. Each tradition/activity is chosen to spark laughter and connection, adding just the right mix of humor, heart, and holiday spirit as you close out 2026.

Quick Setup — No Extra Stress

We want you to feel this is an old-school, easy setup for you as well. Setup takes about 30 minutes to read through and print materials. Most activities run themselves once started. If you choose to do options such as the hot cocoa bar or cookie decoration, you may need a small budget, though these are also perfect for opportunities for the PTO/PTA or parents to sponsor and show their appreciation too.

That Trip to Tahiti (Yes! It’s for Real)

Each year we try to do something special for our supporters, and this year we’re giving away 2 trips to Tahiti as our way of saying thanks. Teachers who have Merriment Tickets left at the end of the week from your game can enter them into our national drawing and find out at 11PM on New Year’s Eve if they need to start packing. Not only are you giving your staff a week filled with laughter and lasting memories, but you’re also giving them a chance at the trip of a lifetime.

Reviews:

“Seeing my custodian find the mistletoe and write down his entry brought such joy to my heart. It was that kind of week. The activities were easy, no stress, and exactly the right balance of laughter with sweetness. I’ve already had three people ask if we can do this again next year, and I would absolutely recommend this to any school.” — Lori Reynolds

“We’ve done several of your games and loved each one, but this one was so special the way the days built upon each other. It might be my new favorite. Our librarian was our Lord of Misrule and she had the entire school in stiches!” — Derrick Martin, Principal

“I have done your holiday programs the last several years with your company and my staff absolutely loves it. They tell me it is the best week of the year. What is typically a hard and busy stretch before the break was made truly amazing because of your planning and creativity. THANK YOU and please keep them coming!” - Dawn Koenin, Principal

Bundle and Save

Get the Holiday Season Bundle by adding Rolling Deep Thanksgiving for only $20. You’ll see this option at checkout.

Rolling Deep is as an easy background of the week game built around humor, gratitude, and the collective wisdom of some of the world’s greatest thinkers. We give you the emails, handouts, posters, and everything you need in easy copy/paste format, so you can create something that feels special without adding to anyone’s plate… except of course for a little pie on that last day.