Winter Break is a festival for boosting joy during the depths of winter.
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 Winter Festivals
per Visit Milwaukee
☀️ Milwaukee Summer Festivals
per Visit Milwaukee
Limping through winter
Milwaukee winters aren't the worst around. Plenty of places are colder, snowier. Minneapolis, Montreal, Iceland. Precisely because we’re cold, but not consistently freezing, we try to get by without the right clothing, boots, gear, snow tires, policy changes, and snow removal techniques that would make winter more pleasant for everyone. And because we don't do winter well here, our quality of life sags. Probably a little bit for everyone, but some groups feel it more acutely.
Elders. Winter means the risk of slipping and falling.
People who have limited mobility, like users of wheelchairs, crutches, walking boots, walkers, and canes. Snow and ice removal needs to improve markedly for these folks to participate safely in outdoor activities in winter.
Adults. Milwaukee adults don't have much programming offered to us other than beer and walking around and looking at things (think Xmas lights or ice carving with chainsaws).
People in a seasonal funk due to changing light levels.
People who don't have the means or cultural knowledge/access to go on a ski vacation.
Accessibility advocates often say that increased accessibility benefits everyone. This is a prime example of a shift in our attitude toward winter would make Milwaukee a better place for all.
Milwaukee deserves joy
and connection in deep 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.
About the Organizer
Kate Pociask (she/her)
Founder, Winter Break
Confession: I am not a winter person.
I started Winter Break because I struggle with winter. The short days, the grey skies, the dehydrated skin, the cold feet; all of it makes me want to stay indoors under a blanket. That was my strategy for most of my life. Then I adopted a dog who turned out to be part Husky. She made sure I went outside every day. I noticed that I felt better, physically and mentally. I learned how to dress for the cold (I had been making a lot of mistakes). With the right clothes, going outside was fine. I went outside, moved around, and spent time in nature.
My Goal
I want to bring joy to Milwaukee in an overlooked season. In 2025, Winter Break had 600 attendees outside enjoying winter. We had 2 consecutive weekends of events and activities and people got to try out new hobbies like winter biking, snowshoeing, winter surfing, and dog sledding. It took more than 260 volunteer hours from just me. Plus many more hours from amazing volunteers who helped arrange and staff the events.
Here is what happened:
In 2025, 600 people came out to embrace winter
$0 for attendees
8 people dunked themselves in Lake Michigan for their health
5 miles worth of dog sled rides were given out
400 hot cocoas served
10 bonfires burned 1/2 cord of wood
10% of the people who attended came from out-of-state (?!) from as far away as Florida, Texas, New York, and California
History of Winter Break
-
February 2025
Havenwoods State Forest
Milwaukee, WI
Snowy Dreamland -
February 2025
Bradford Beach
Milwaukee, WI
Brave New Sports -
February 2024
South Shore Park
Milwaukee, WI
Sunny Smiles and S'mores
