The holidays are the perfect time to slow down, get cozy, and spread a little extra kindness—and what better way to do that than through Merry Mail, our annual holiday pen pal program? This cheerful tradition invites Braintree students to connect with a new friend, exchange festive mail, and share the joy, creativity, and warmth of the season.

Whether students love writing, drawing, crafting, or simply spreading smiles, Merry Mail gives them a fun and meaningful way to learn about others while practicing writing skills, communication, and gratitude.

This year, we’ve created a Holiday Pen Pal Checklist of ideas and prompts your student can use in their letters. They can choose a few for each round of mail—or challenge themselves to complete the whole list!

Creative Items Students Can Include in Their Merry Mail

A pen pal letter becomes even more special when fun surprises are tucked inside. Students can choose simple, flat items that bring their personality to life and invite their pen pal into their world.

Here are some student-approved favorites:

• A personalized holiday recipe card

• A hand-drawn ornament design

• A mini Winter Bucket List

• A coloring sheet (simple, festive, kid-made designs encouraged!)

• A paper snowflake or holiday bookmark

• Holiday jokes or riddles

• A cut-and-fold gingerbread house outline

• A “Dear Santa” writing template

• A postcard-style drawing of winter sights in their hometown

These small touches help students practice creativity and fine-motor skills, and they make receiving mail so much more magical!

Download your own Braintree Merry Mail Templates here!

Holiday Writing Prompts to Spark Joy and Connection

Writing to a pen pal is a chance to share a little piece of your world. These prompts help students reflect on meaningful traditions, express themselves creatively, and build connections with other Braintree friends across the state. Encourage your child to pick a prompt or two for each Merry Mail exchange!

• Share three of your favorite holiday traditions and why they matter to your family.

• Describe your perfect winter day—what would you do, eat, and explore?

• Write about your favorite holiday memory (funny, sweet, or surprising!).

• Tell your pen pal about a winter adventure you’ve had—sledding, baking, decorating, or something silly.

• Write a short Christmas story featuring a reindeer, an elf, and a lost present.

• Describe your family’s favorite holiday foods and what makes them special.

• Share what kindness means to you during the holidays.

• Create a holiday wish list made entirely of experiences, not things.

These prompts naturally strengthen writing skills, sequencing, and descriptive language—all while making letter-writing fun.

Fun Mini Activities Students Can Send

For students who love games, hands-on creativity, and sharing activities, these mini add-ins are a huge hit:

• Holiday scavenger hunt list (“Find something that sparkles…”)

• A Secret Kindness Challenge card

• A one-page “Elf Report” imagining what their elf might be up to

• A magical snow globe drawing prompt

• Christmas-themed Mad Libs

• Holiday Would-You-Rather questions

• A festive maze or word search they create

• A “Build Your Own Christmas Tree” cutout to color and decorate

These activities turn Merry Mail into an experience—not just a letter.

Conversation Starters & Questions to Build Friendship

Not sure what to write? These simple questions help spark a real connection:

• What’s your favorite winter treat?

• Do you celebrate any special traditions?

• What’s your favorite Christmas movie or holiday song?

• How does your family show kindness during this season?

• If you could invent a new holiday, what would it be?

• What are three things you’re grateful for this year?

Learning about others helps students grow empathy, curiosity, and communication skills—all essential parts of the learning journey.

Add a Little Extra Holiday Magic

Encourage your student to personalize their Merry Mail even further:

• Create a holiday-themed bookmark

• Decorate their letter with doodles or stickers

• Share their favorite quote about joy or hope

• Add a simple STEM challenge (“Build a bridge from toothpicks and marshmallows!”)

• Include a blank gingerbread person template to decorate

• Share a “Holiday Playlist” of song titles they love

Every piece they add makes the exchange more memorable.

Why Merry Mail Matters

Merry Mail is more than a seasonal activity—it’s an opportunity for students to build communication skills, practice writing, and experience the joy of thoughtful giving. Exchanging letters helps students connect with peers across the state, learn about different families and traditions, and celebrate community during a time of year filled with warmth and goodwill.

By participating in Merry Mail, students build:

• Writing confidence

• Creativity

• Empathy

• Community connections

• A sense of holiday joy and excitement

And above all, they get to make someone’s day a little brighter.

Enjoy and be merry!

The Braintree Academy Team