Winter Break is a festival for boosting joy during the depths of winter.

Guiding Principles
1st: The event is free.
2nd: All are welcome. 🏳️‍🌈🇦🇶
3rd: It is outside, mostly.
4th: Activities are fun and weird.
5th: No power sports, no alcohol.

Seasonal Lopsidedness.

Milwaukee is the “City of Festivals,” but only for part of the year. Our summer calendars are jam-packed and they fly by. In contrast, our winters are desolate. Milwaukee deserves joy and connection in deep winter.

Milwaukee Winter Festivals
per Visit Milwaukee

Screenshot from the January and February Visit Milwaukee Events Calendar. Each month has just 3-4 events in it.

Milwaukee Summer Festivals
per Visit Milwaukee

Screenshot from the July Visit Milwaukee Events Calendar. It features 30 events.
Screenshot from the June Visit Milwaukee Events Calendar. It features 24 events.

History of Winter Break

  • A bernese mountain dog with flecks of snow on its fur stares directly into the camera. The hands and bodies of its owners are behind them.

    Snowy Dreamland

    Havenwoods State Forest
    February 2025

  • Brave New Sports

    Bradford Beach
    February 2025

  • A group of 7 strangers are warming their hands around a fire pit on the beach. In the foreground, a man and his son are loading double marshmallows onto sticks to make s'mores.

    Sunny Smiles and S'mores

    South Shore Park
    February 2024

A group of people in swimsuits walking away from the camera, and into a cold lake.

 

Subscribe to our newsletter

Subscribe to our newsletter

About the Organizer

Kate Pociask (she/her)
Founder, Winter Break

Headshot of Kate, the organizer, wearing her winter hat and her winteriest face

Confession: I am not a winter person.

I started Winter Break because I struggle with it. The short days, the grey skies, the dehydrated skin, the cold feet; all of it makes me want to stay indoors under a blanket. But I adopted a dog who turned out to be part Husky. And she made sure I went outside every day. I noticed that I felt better, physically and mentally, if I dressed for the cold, went outside, moved around, and spent time in nature.

My goal with Winter Break is to bring joy to an overlooked season in Milwaukee. In 2025, Winter Break had 600 attendees outside enjoying winter. With the success of the past years, I look forward to bringing the event back and coaxing more people out of hibernation.