10 Tips for Winter Break with Upper Elementary and Middle School Learners

By Kathleen Brigham and Kat Ressa for The Tutoring League of New York

The winter holiday break offers a delightful opportunity for you and your family to relax and share quality moments, but it’ll be over sooner than you realize! The foundation of children’s school success lies at home, and even small steps can significantly impact your child’s school experience. To ensure a smooth transition back to school after the New Year and keep your upper-elementary or middle school child’s skills sharp, consider the following tips:

1. Establish a Realistic Routine and Plan Ahead

While it’s great to let go of structure, deviating too much from your usual routine can lead to a challenging adjustment when returning to the regular schedule. Maintain some consistency, especially with mealtimes and bedtimes. Even though it’s tempting to allow your kids to stay up late and sleep in, sticking to a routine helps. Use a calendar to schedule activities.

2. Make the Most of Unstructured Time

Create a list of activities for your kids to engage in during unsupervised periods, such as when you’re working. This ensures that they have productive and enjoyable ways to spend their time.

3. Prioritize Fun During the Winter Break

School breaks are an excellent opportunity for families to reconnect and make lasting memories. Plan a variety of activities that cater to everyone’s interests, including outdoor adventures and indoor activities. Involving all family members in the planning process ensures that everyone feels included and excited about the upcoming activities.

4. Encourage Reading for Pleasure

Take advantage of this time to explore your child’s interests through reading. Whether it’s holiday stories or the latest release from their favorite series, winter break is perfect for reading for enjoyment! Encourage relatives to give books as holiday gifts and consider family reading sessions in front of the fireplace.

5. Check In With Your Child and Acknowledge Their Efforts

As the first half of the school year concludes, have a conversation with your child about their experiences. Discuss their favorite and challenging subjects, the effectiveness of any school accommodations, their social interactions, achievements, and goals for the upcoming year. Acknowledge their hard work and celebrate their accomplishments.

Winter break is also a great time for parents to evaluate what has and has not been working at home. As shorter days and longer seeming nights set in, remember, effective communication is key. Instead of hijacking cookie-making moments, plan a dedicated time together to address any challenges. When you are ready to tackle school and study routines, setting a timer, turning on some music, and involving your child in organizing or planning can make interactions around such topics more engaging, especially for middle school-aged children.  Here are some areas to think about:

6. Study Space

Assess whether the current study area is conducive to productivity. Is your child working at the kitchen island or in their room? If it doesn’t seem to be working, agree to switch it up after the break and try a different space.

7. Organization Within Study Spaces

Ensure that study materials are easily accessible. Are scrap paper, pencils, and other study items easy to find? What about that backpack? Or that dreaded accordion folder…is it stuffed to the gills?

For many students who worry about needing items, we suggest putting old papers and materials in a folder and placing the material in a closet. We tell students that they can keep things there until the end of the year. Nine times out of ten students never go back to those folders but it does help ease the stress of “but what if I need that?”

8. Establish or Reaffirm Routines

Reflect on daily schedules and address any recurring issues, such as being late for school. Approach these discussions with a collaborative mindset, seeking input and ideas from your child for solutions. For instance, if your child is late for school every day, winter break is a good time to bring up that conversation.” I’ve noticed that we are running late for school every day. Do you have some ideas about how we might do that differently after the winter break?”

Then use the menu approach and ask any of the following:

“Do you think it might help to get up five minutes earlier?”

“Could you pack your things for school the night before?”

“Could you create a getting-to-school playlist, knowing that when that playlist ends, we’ve got to leave?”

Giving them options makes them feel as if they’re a part of the solution and encourages independence.

9. Determine Non-negotiables

Set essential rules and expectations together as a family. These might include a post-school check-in to help manage the workload efficiently, implementing no-phone study time, and restricting phone usage overnight. Introducing these ideas over a break gives your child time to prepare (and, yes, to complain!) before it is implemented.

10. Use Positive Reinforcement

Don’t forget the good stuff!! Use the break to highlight and appreciate improvements. Acknowledge your child’s organizational skills, time management, and positive changes. Let them know specifically what you are proud of and what improvements and changes you see.  Especially make sure to highlight where you see them being independent. “I just want to let you know how different it is this year from last year. Your desk is so much more organized,” or “you are getting out the door on time on a much more regular basis.”  Or “ I’m really happy to see that you’re putting aside your phone while you study.”

By focusing on these tips during the upcoming school vacation, parents can engage in important observations and conversations that allow time and space for reflection and change. But don’t forget, making cookies, completing a craft together or simply taking a family hike can do wonders to set the course for success at school this winter. So, enjoy the holiday season even as you plan ahead for the New Year!

Kathryn (Kat) Ressa is a New York State licensed Speech-Language Pathologist earning her master’s degree from Adelphi University. She has a unique interest in feeding and language development, and also holds an Advanced Certificate in Pediatric Dysphagia from New York Medical College. Kat specializes in language disorders and utilizes a play based approach to facilitate language development. Her research has focused on pediatric dysphagia, language development and literacy, and she has contributed to several academic papers on these topics. www.ressaspeech.com

Kathleen Brigham possesses a Bachelor’s degree from Middlebury College and a Master’s in Educational Administration from Columbia Teachers College. She worked as an admissions director in New York City while also teaching art history and grammar classes. Upon moving to London, Kathleen co-founded School Choice International, an education consulting company that counseled families looking for schools in London. Inspired by the learning challenges and opportunities experienced by students during 2020 and after, Kathleen founded Brigham Learning, designed to reach as many students as possible. www.brighamlearning.com