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Winter Break Activities

Posted on December 22, 2025December 23, 2025 by Teesta Bhola-Shah

By Teesta Bhola-Shah

“This winter break is going to be so hype!” you say to your friends at the lunch table. You’re already thinking about all the fun you’re going to have, no school, no homework, just hanging out with your friends. 

And then break starts. Your groupchat goes silent, and suddenly everyone seems to be busy. If you can find a time to hang out with your friends, the age-old question will arise yet again: What should we do? 

To prevent you from getting into this all-too-common situation, I have a list of easy, fun ideas to do with your friends (or even yourself) over winter break. Enjoy!

  1. Baking Christmas cookies

Check out a quick recipe and you can make delicious Christmas cookies in less than an hour ith your friends! With some red and green sprinkles and icing, you can decorate the cookies and shape them however you want. Plus, you get a sweet treat at the end, arguably the best part. 

  1. Sledding

That is, if it snows again over break. Hopefully it will! Winter break is the perfect excuse to actually enjoy the cold. There are some great hills in Chatham for sledding too, especially the ones at Milton and by the power lines. Of course, if you’re sledding with friends you could do all the other snow activities—make a snowman, have a snowball fight, make hot chocolate when you get inside!

  1. Watching Christmas movies

When it’s freezing outside and no one wants to leave the house, a movie night is the move. There are so many good Christmas movies, so you won’t run out of ideas for things to watch. Everyone thinks that the Nightmare Before Christmas isn’t a Christmas movie, but I would argue that Christmas is the best time to watch it (ask people what they think). 

  1. Secret Santa (but easier)

If you don’t have time to plan a secret Santa, let me put you on to this idea: drive to Walmart, or Target, or a similar store. Set a budget, then have names randomly assigned for Secret Santa. Within your budget, take 20 minutes with your friends to buy your person a gift within the budget from the store. After the 20 minutes is up, you and your friends can all exchange gifts, and it’s an easy Secret Santa!

  1. Thrifting

Trust me, thrift stores are actually really good around this time of year. You can find sweaters, cardigans, boots, scarves, basically all the winter clothes everyone wants right now. Going thrifting with friends is also way more fun than going alone, because you can try stuff on, get opinions, and make fun of outfits you’d never wear. It’s cheap, fun, and you might actually find something unique.

  1. Volunteering together

Winter break is also a really good time to give back. During the holidays especially, there are a lot of places that need extra help. Key Club has a lot of events that people can volunteer at, like the Jaycees Christmas tree sale. You and your friends could volunteer at a food pantry, animal shelter, or a local community event. It’s a good way to do something meaningful while still spending time together, and it honestly feels nice to help people during the holiday season.

  1. Trip to NYC

If you’re trying to do something a little bigger, a day trip to New York City is always a good option. Bryant Park’s Winter Village is super fun to walk around, especially at night, and there are a ton of little shops and places to get hot chocolate. You can also go shopping, explore, and obviously get really good food. 

So next time you wonder to yourselves, what should we do over break? You’ve got a full list of ideas here!

  • Teesta Bhola-Shah
    Teesta Bhola-Shah

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