A festive journey through history—because your staff deserves to be celebrated.

What’s is it?

Treat your staff to a weeklong holiday adventure that blends laughter, warmth, and the timeless wisdom of traditions old and new.

In an age of constant notifications and endless scrolling, we all need a reason to pause, unplug, and reconnect with what matters most. Old School Holiday delivers just that, a chance to rediscover and reconnect as you head into 2026. Each day features hand-picked traditions throughout the centuries, carefully chosen to spark joy, bring people together, and remind us of the simple magic that can happen when take a pause.

How much?

$69/school

100% Satisfaction Guarantee

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

What is the game like?

Everything begins with a humorous email kickoff (email is old-school, right?) detailing how you’ve researched some holiday traditions from around the world through the centuries. As a treat for your teachers and staff, you’re going to give it your all to bring these traditions to life.

From the quirky and modern to the downright ancient, these “pop-up traditions” will fill your halls with cheer, connection, and a few good laughs.

Some traditions will make you smile, some will surprise you, and a few might even make you stop and think about what truly makes this season special. It’s the perfect way to wrap up the year—with a little history, a lot of humor, and plenty of heart.

How much time is required?

Setup takes about 30 minutes to customize your challenges and setup the gameshow wheel station. Each day then requires about 15 minutes to update challenges and grab bag prizes. If you do the optional staff party at the end, you can do it as big or small as you wish: as a drop by party area during lunch, an after school event, or even an off-site bash. Everything is planned for you with games and music and ready to go.

Reviews:

“This week has brought back so much laughter and fun! This sweet teacher is my special education high school teacher and she is adored by all. She is normally quiet and nose to the grindstone doing paperwork for her IEP‘s and helping her students. Her Challenge spin today was to throw marshmallows at unsuspecting coworkers and earn points. She caught me off guard as she pelted me with marshmallows as you can see from this picture. I can’t say enough how much this week has been a stress release to my teachers who have worked so hard this past year as it has been one of the hardest years ever in education. Just hearing my staff laugh again and just be silly has brought great joy to my heart. To my administrator friends, you should really do the Holiday Road challenge game show week because it’s worth every penny!” -Angela Haney-Girgis

“I am going to give a big plug to Class Team Building for the Holiday Road Week! It's the most fun we have had as a staff in a long time!! I have a staff that is super fun and loves to have a good time so the challenges were right up our alley!! You should definitely check into them for future culture building activities!!" - Rachel Keeling-Moehle, Principal Life Facebook Group

“I saw diet Coke coming out of our librarian’s nose and it was awesome! People are already asking when we can do more of these.” -Christopher Di Diego