Letters to a Grandchild: A Year’s Worth of Ideas

​Ever wondered why or how to write a letter to your grandchildren? Here’s the answer to both.

Do you have any letters from your grandparents? If you do, you know how special they are. The written word is a powerful connector, and letters are physical proof that you value your relationship with your grandchild. There is no better way to link generations than regularly writing letters to a grandchild!

Grandparents often ask, “What should I write to my grandchild?” It can be especially hard when your grandchild is too young to respond. You sometimes feel as if you are writing into a void! That’s why I’ve put together a year’s worth of Letters to My Grandchild Prompts. Read them below, then keep reading for tips on writing to different ages and how to make this a part of your grandparenting routine.
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Each month has an overall theme and some questions to get you thinking about stories you can share. The questions are just starting points, and some may not apply to your family. Feel free to go off on your own tangent after reading the prompts!

January: Share stories about resolutions.

• How do you approach changing your habits?
• Do you make resolutions? Do you keep them?
• Do you remember any resolutions you made as a child?
• What do you wish you could get better at this year?

February: Share stories about Valentine’s Day.

• What was Valentine’s Day like when you were in school?
• Did you ever give a valentine to someone you had a secret crush on?
• Do you like celebrating it today?
• Do you like candy hearts or chocolates better and why?
• Did you make or buy valentines when you were young?

March: Share your thoughts about spring.

• What do you like about spring?
• Did you ever go on trips over spring break as a child?
• What makes you feel like it’s spring?
• Is there a season you like best and why?
• Do you have any rituals you follow in the spring, like cleaning the house or planting a garden?

April: In celebration of Earth Day, share stories about nature.

• What do you enjoy about being in nature?
• Do you like the forest, beach or desert and why?
• What do you remember about playing outdoors as a child?
• What’s your best memory of spending time outdoors with their parent?
• What do you look forward to doing outdoors with them?

May: Share some stories about your family tree and its roots.

• What’s your favorite story about your grandparents?
• What’s your favorite story about your parents?
• Where did your family come from?
• Did you move around as a child?

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June: In honor of the traditional month of weddings, share some family love stories.

• How did your parents meet?
• What was your wedding like?
• What about their parents’ wedding?
• How old were you when you met their grandmother/grandfather?
• Were you ever in a wedding party as a child?

July: Share favorite summer memories.

• What are your favorite summer memories from your childhood?
• What smells and sounds do you remember from summer as a child?
• How did you like to spend summer days?
• What do you like about summer now?
• What did you and their parent do during the summer?

August: Share your thoughts and stories about traveling.

• Do you like to travel? Why or why not?
• Describe a memorable trip.
• Where would you like to take your grandchild someday and why?
• Did you ever travel with your grandparents?
• What’s your favorite place you’ve ever visited?  

September: Share your memories of your school days.

• What was your school like as a child?
• What did you like or dislike about school?
• What do you remember learning that has been useful in your life?
• What do you think is different about school now?
• Who was your favorite teacher and why?

October: Share memories of Halloween.

• What did you do for Halloween as a child? Do you remember any costumes you dressed up in?
• Did you ever go to a Halloween party?
• What did your neighborhood do?
• How is Halloween different today?
• What’s your favorite candy, and has that changed since you were young?

November: Share memories of news you have lived through.

• Where did you get your news when you were young?
• Do you remember any world events that impacted you?
• Did you know anyone famous?
• Were you or their parent ever in the newspaper?
• What’s happening in the world today that you think they will remember?

December: Share your holiday stories.

• What are your favorite holiday memories?
• What traditions did you enjoy as a child? As a parent?
• What was one of their parent’s favorite gifts or holiday foods?
• What holiday foods did your grandparents make?

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Now available: Grandparent Love Letters!

Get your Grandparent Love Letters in our shop! This set of 12 darling letters will help you write a monthly letter to your grands. These beautifully designed PDF’s will delight your grandchild and create a written record of the memories you want to share. Learn more.

Writing to children under five
Before your grandchild can read and write, your letters are not going to be very important to them. That doesn’t mean you shouldn’t write them, however! When they are older, they will have a written record of how often you thought of them, and they’ll treasure the stories you’ve shared. If your grandchild is very young, you may want to write these letters and collect them for when they are older. You could also send them and ask parents to keep them somewhere safe. 

Writing to school age children
Once children are old enough to read and write and understand the passage of time, they will start to appreciate all the stories you share. As they get older, your letters can be an important way to get to know one another. You can begin to pose questions in your letters, asking them to call or write you with their answers. Don’t be discouraged if you don’t get responses, however. Keep writing and asking, so they know you are interested in their lives.

Writing to teenagers
Letters to teenagers can continue to ask questions, and you can begin to share more of your life’s wisdom. You can offer encouragement and share stories about struggles you had as a teen. They will love stories about their parents and aunts or uncles. Whatever you do, keep writing. Teens need to know that there are adults in their lives who will be there for them no matter what. (See our post on 7 Ways Your Teenage Grandchild Needs You.)
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How to Write a Letter to Grandchildren
There are two parts to writing a letter to your grandchild. One is the actual writing. Your letters don’t need to be long, or perfectly written.  You can write on scrap paper. You can write on special stationery so letter is clearly from you. You can use your vintage typewriter, or compose it on your laptop, then print and send it. In other words, you can do whatever feels easiest, most fun, or most meaningful to you. (For ideas on how to make your letters more fun, read this post!)

The second part is sometimes the hardest, and that’s actually doing it. The best way for many of us is to block a regular hour on our calendar dedicated to writing. If your grandchild was born on the 7th of the month, put a reminder to write on the 7th of every month. Or set aside an hour on the first Saturday morning for letter writing. Like any habit, it will take practice and reminders before it becomes part of your routine.
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Will writing letters to your grandchild be a part of your routine this year? Please let us know in the comments!
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