9 Free Winter Festivals Happening This Year

Winter is where we shine, Milwaukee. When you summon up the strength to brave the cold, head to one of these *free* winter festivals to warm you up on the inside and out.

1. Cool Fool Kite Festival

January 1, 2020

Gift of Wings Kite Store in Veterans Park

1300 N. Lincoln Memorial Dr., Milwaukee, WI 53202

(414) 273-5483


(This event happened already – mark your calendars for next year!)

This free annual kite festival held on New Year’s Day offers free hot cocoa and coffee, snacks, giant kites, ice artists, ice carving lessons, and hot food for purchase. You can bring your own kite to fly or purchase one at Gift of Wings.

2. Winterfest at the Boerner Botanical Gardens

January 19th, 2020 from 10:00 – 2:00

9400 Boerner Dr., Hales Corners, WI 53130

(414) 525-5600


Cure your cabin fever with winter nature walks, indoor & outdoor activities, hot drinks and FREE family fun! There will be seasonal kids’ crafts, learning about winter trees and animal tracking, and the opportunity to create a sugar “ice” sculpture. Take advantage of free admission and free Educator-led family winter nature walks. Winter walks are roughly 60 minutes long and depart regularly throughout the event.

3. Waukesha Janboree

January 17-26, 2020


Get it? “January” and “Jamboree” are combined to create “Janboree”! This epic event opens with a special ceremony that includes a dance, live music, and fireworks outside on the Fox River. Activities throughout the weekend include ice sculpting demonstrations, a pancake breakfast, trolley rides, ice bocce ball, indoor ice skating at Eble Arena, ice fishing clinics, horse-drawn wagon rides, stargazing planetarium shows, nature activities, and more!

4. Winterfest at the Urban Ecology Center

Saturday, January 25th, 2020 from 10:00-2:00

Washington Park

1859 N. 40th St., Milwaukee, WI 53208


Celebrate winter, friends, and family at Washington Park! If there’s snow, there will be sledding and ice skating on the Washington Park lagoon. If the snow’s a no-show, you can enjoy guided nature walks. Regardless of the weather you can do arts and crafts and eat a slice of homemade pie. See you outdoors!

5. Winter Carnival at the Lynden Sculpture Garden

Saturday, January 25th, 2020 from 10:00 – 4:00

2145 W. Brown Deer Rd., Milwaukee, WI 53217

Visit Website

The 10th annual Winter Carnival features artist projects, games,drop-in studio activities, and surprises orchestrated by Michael Lagerman. Watch for a large-scale land art project from guest artist Richard Shilling. Gary John Gresl will create a Pop Up sculpture titled “A Ballad for Disappearing Beasts.”

6. Winterfest at the Corners of Brookfield

January 17-19th, 2020 Corners of Brookfield

​Free! ($5 for skating)

The Corners will be transformed into a winter wonderland with an ice rink in Market Square, various interactive ice sculptures and winter activities for all, including ice mini golf, tic tac toe, and face painting. Meet and skate with the Milwaukee Admirals mascot, Roscoe!

7. Winter Frolic at the Mequon Nature Preserve

February 1st, 2020

8200 W. County Line Rd., Mequon, WI 53097


Head to the Mequon Nature Preserve for a free festival that includes dog sled demonstrations, tractor rides, sleigh rides and carriages, , ice fishing, bonfires, snowman building, food trucks, and more. Indoor activities include a kids craft corner with Bookworm Gardens, a winter marketplace, game room, live music, and more!

8. Woolly Bear Winter Festival

Saturday, Feb. 8, 2020 from 11:00 a.m. – 3:00 p.m.


The River Revitalization Foundation invites you and yours to their office located on the Milwaukee River for some outdoor winter fun! This is a FREE family-friendly event open to the public featuring face painting, cookie decorating, DIY bird feeders, ice skating and sledding (bring your own skates and sleds), plus meeting the Door County Sled Dogs from 12:00 – 1:30 p.m., and come hear the “Northern Lights” radio from from 1948 starring Woolly Bears. They’ll be offering hot cocoa and hot dogs & s’mores to roast. Donations appreciated.

9. Winter Festival in Cedarburg

February 15-16, 2020

W63 N641 Washington Ave., Cedarburg, WI 53012

Visit Website

Cedarburg is magical in the winter, and outdoor fun abounds at their Winter Festival. Enjoy a winter weekend of family-fun festivities – camel rides, chili contests, ice-carving contest, costumed bed races, barrel racing, grand parade, marketplace, children’s activities, tractor-drawn hay rides, plus sign-up to tee off with the “IceBurg Open Golf Tournament” in Cedar Creek Park and special events at the Cedar Creek Settlement, including free wine samplings and live music on both Saturday and Sunday.

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