Free Silly Holidays Classroom Calendar Set

While students and families are enjoying summer break, many teachers and school leaders are already thinking ahead to the new school year. Planning ways to connect with students, support teachers, and build a positive, welcoming vibe from day one is no small feat. And with so much on your plate, finding something easy and fun to bring everyone together is a big win.

That’s why we’ve partnered with Staples Business to bring you this 2026–27 Silly Holidays Classroom Calendar. This free printable is an easy, ready-to-use way to add joy and engagement all year long. The download is packed with fun, unexpected “holidays” that spark connection, creativity, and school-wide participation.

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Free Printable 2026-27 Silly Holidays Classroom Calendar

Get 12 months of fun, easy ways to engage students and staff all year long. Enter your email in the form on this page to get instant access.

Images of two calendars from the Staples Business Silly Calendary downloadable — We Are Teachers

What you’ll get with this downloadable:

The May and June calendar from the Staples Business silly calendar printable — We Are Teachers

12 Months of Reasons To Celebrate

Running from July 2026 through June 2027, this downloadable calendar set gives you a full year of ready-to-use fun. Every month features unique silly or quirky holidays, perfect for sparking laughs, conversations, and easy engagement in your classroom or school. (Don’t worry, the traditional holidays are on there too!) Just print and go, or display digitally for quick daily inspiration. It’s a simple way to add joy, build community, and keep students (and staff!) smiling all year long.

Notes Sheet

This companion notes sheet gives teachers a dedicated space to plan, reflect, and build activities around each silly holiday. Use it to jot down quick ideas, discussion prompts, or extension activities that tie directly to the calendar. It’s perfect for turning a fun daily moment into something meaningful—whether that’s a quick writing exercise, SEL check-in, or class celebration.