February 28 2026

Havenwoods State Forest

Save the Date:

Milwaukee, Wisc.

A twenty-something man and woman are testing out snowshoes and giving the peace and thumbs up sign. In the background is snow and hiking trails.

Winter Break is a winter festival for boosting morale during the long cold season.

Milwaukee needs something to look forward to after the holidays have ended, but the grey skies have not. 

All areWelcome

Winter Break invites you out of hibernation for a free festival for all ages, experience levels, bodies, and genders. We offer activities that are gentle, fun, and surprising.

This event flexes with the weather. The forecast doesn’t need to look golden. If we have cold, snow, and ice, that just unlocks more activities!

PAST EVENTS

An adult woman and a small girl are dressed in snow pants, smiling, and tossing snow at the camera.

SNOWY

DREAM LAND >

Havenwoods State Forest
February 2025

4 hikers are going for a winter hike with decorated hiking sticks
Two women are standing next to fat tire bikes that they are testing out.
A team of dogs is pulling two men in and on a sled.

more +

BRAVE

NEW SPORTS >

A young woman lounges on a folding lawn chair. She is wearing gloves and holding a marshmallow toasting fork over a bonfire.
A goup of 6 people are cold dipping in Lake Michigan. They are wearing bathing suits, hats and mittens.
A woman is dog sledding on the beach. The dogs are pulling a scooter-like cart. In the background is Lake Michigan

more +

Bradford Beach
February 2025

A group of 7 strangers are huddled around a bonfire on the beach. They are smiling and warming their hands. In the foreground, a man and a small boy are roasting marshmallows to make s'mores.

Beachy

smiles and s’mores

South Shore Park
February 2024

 more +

Ways to support the festival…

A graphic showing hands holding on to drawn dollar signs. There is a dotted texture in the background, and some fun shapes.

Milwaukeeans need something to look forward to in deep winter. This event is free and open to all, goes on no matter the weather, and brings free recreation, fun, education. Most importantly, it’s a chance to get out of the house and be in community.

Become a Sponsor

Partners and Sponsors

Visit Milwaukee
Experience Milwaukee
Savage Logo

WE ACKNOWLEDGE

the stewards of these lands
& waters that came before us

Milwaukee and Wisconsin are or have been home to people from the sovereign nations of:
| Oma͞eqnomenew-ahkew (Menominee) | Bodwéwadmi (Potawatomi) | Očhéthi Šakówiŋ (Dakota/Lakota)  | Kiikaapoi (Kickapoo) | Hoocąk (Ho-Chunk) | Myaamia (Miami) | peewaareewa (Peoria) | Ojibwe (Chippewa) | Onyota'a:ka (Oneida) | Odawa (Ottawa) | Meskwaki (Fox) | Muh-he-ka-neew (Mohican) | oθaakiiwaki (Sauk) | and more. |

Today, 7,000+ Milwaukeeans identify as Native, the largest concentration of Native people in Wisconsin. We recognize that the ancestors of the peoples of these nations preceded and survived European Colonialism, enduring racist and xenophobic policies aimed at cultural genocide and cultural erasure, like re-education at boarding schools, destruction of sacred sites, land seizures, and forced relocation. We acknowledge this traumatic history, the effects of which can still be seen today in the form of Murdered and Missing Indigenous Women, adverse health outcomes for native peoples, and the cycle of intergenerational poverty resulting from dispossession of their land and thus the resources on it.

We attempt to further dismantle white supremacy by educating ourselves about the sovereign nations whose land we are on, by reading work by native scholars and writers, and by donating to native causes and supporting native-owned businesses. We invite everyone to do likewise.