50 Things To Do During Winter Break in 2020

Updated: Dec 16, 2020

This Winter Break's mantra: There's no such thing as bad weather, just bad clothing.

We've hand-picked 50 things to do with your kids to liven up your "vacation", and many of them are outside in the fresh, cold air. (Special Bonus: 30 of them are completely FREE!)

You'll find a mix of outdoor activities, indoor destinations (with safety precautions in place), drive-through destinations, and virtual options.

We are so thankful to our partners at the Child Advancement Network(CAN) for sponsoring us this season. CAN was established as a broad-based, comprehensive, and innovative approach to child health via partnerships, advocacy and collaborations aimed at advancing the wellbeing of children across domains of health. Learn more about them here.

***Winter Break Giveaway***

Tag us on Instagram in photos of your family doing any of the ideas listed below. You'll automatically be entered to win a Wisconsin Winter Survival Gift Package that includes a sled, gourmet hot cocoa, and surprises from our favorite local businesses.

Unlimited entries!

1. Domes Holiday Show

Photo Credit: Instagram, @the_greenery_608

524 S Layton Blvd, Milwaukee, WI 53215


The Domes are all decked out for their annual holiday show with an impressive display of poinsettias and winter greenery.

You need to reserve a time slot online before you go, masks are required, and you follow one route through the three domes.

2. Betty Brinn Glomado Workshops

The new cultural workshops offered by @bettybrinnchildrensmuseum and Glomado are all online, live, and taught by teachers both local and from around the globe. The workshops are limited to just six participatns so you're guaranteed individual attention.

Example workshops:

🇬🇭: Make bracelets with Krobo beads with Kingley Otu from Ghana

🇮🇳: Create a Macrame Wall Hanging with Ashi Husain from India

🇱🇻: Make Latvian Paper Dolls with Daine Elksne from Latvia

You have to check this out! Find them at bbcmkids.org/playinthecloud.

3. Ice Skating at Red Arrow Park (Free + Skate Rental)

Dec. 24, 2020 - March, 2021


Photo Credit: @littlexlittlephotography

Reserve your 90-minute timeslot online, grab your skates and mask, and head to Red Arrow Park! Downtown Milwaukee's outdoor ice rink is free to use when you bring your own skates. Affordable skate rentals are also available.

To find other ice skating locations in and around, click here.

4. The Wisconsin Christmas Carnival of Lights

Jellystone Park Camp-Resort (8425 WI-38, Caledonia, WI 53108)

Saturday, November 21 - Dec 31, 2020 (Closed 11/23-11/27 & Christmas Day)


It's your last chance - And without the huge line this time! Just 20 minutes south of Milwaukee, experience a unique drive-through holiday light show that stretches more than a mile with over 1.5 million lights.

5. Day Trip: Dream Park in Kenosha (Free!)

3100 14th Ave. - Kenosha, WI 53140


Bundle up and head to the 15,000- square-foot Dream Playground, Kenosha's first fully accessible playground. More than 3,000 volunteers worked to raise support and construct this amazing playground. It's fun in all seasons!

6. Frosty Free Week at Milwaukee County Zoo (Free!)

Free admission for all visitors

Advance Online Reservations Required Regular parking / attraction fees apply

Dec. 26 - 31st, 2020


You’re going to want to reserve your time slot soon for Frosty Free Week at the Milwaukee County Zoo because it will definitely fill up.

That’s right! From December 26-31, the Zoo is free to all visitors. But a reservation is required, and so are masks.

Stop by and say Happy Birthday to Snow Lilly, the polar bear. She just turned 36 birthday this month!

7. Pajama Story Time (Free!)

Check out the lineup of virtual Story Times and activities that your Milwaukee Public Library is offering over Winter Break! Pajama Story Time is SO much fun.

8. Horse-Drawn Sleigh Rides at Apple Holler

5006 S Sylvania Ave, Sturtevant, WI 53177


The horse-drawn sleigh ride experience at Apple Holler’s family farm will make you feel like you stepped inside of a glistening winter snow globe.

9. Country Christmas at the Ingleside Hotel

2810 Golf Rd., Pewaukee, WI 53072 November 27th 2020 – January 2nd 2021 5:00 – 9:00 PM Sunday – Thursday 5:00 – 10:00 PM Friday, Saturday & Holidays $20/carload thecountrychristmas.com

*After* the holiday is a great time to see the lights, without the line! The Country Christmas Trail features over a million holiday lights festively displayed on over a mile-long trail. As guests drive through the countryside, they will experience enchanting animated figures and holiday scenes from the comfort of their car.

10. Kayla's Playground (Free!)

Franklin Woods Nature Park, 3723 W. Puetz Rd., Franklin, WI


Look at it this way: The colder is it, the more of the playground you'll have to yourself! Kayla's Playground is a must-visit. Check out the full review here.

11. Tubing at The Rock

7900 Crystal Ridge Dr., Greendale, WI 53129


You can ski, snowboard, or just slide down the tubing runs at The Rock Snow Park.

12. WI Humane Society Virtual Winter Break Camp


During this live virtual camp, kids will be encouraged to connect with other campers, make animal-related crafts, and participate in lessons that get them out of their seat, moving and shaking! Kids will have a chance to virtually meet animals available for adoption.

13. Hike at Hawthorn Glen (Free!)

1130 N 60th St, Milwaukee, WI 53208


Hawthorn Glen is near the border of Milwaukee & Wauwatosa, and it offers the perfect length loop for little legs. There are postings along the way so you can learn about the history and wildlife around you. There are stairs to climb at the back of the property for a good view, and a fun hill for the kids to slide down. There's also a small playground and sandbox.

14. Candy Cane Lane (Free + Donation)

West Allis between 92nd-96th St. and between Montana and Oklahoma Ave. Nov. 27th - Dec 27th, 2020 6-9 p.m. Monday - Thursday | 6-10 p.m. Fridays | 5-10 p.m. Saturdays | 5-9 p.m. Sundays candycanelanewi.com

See Candy Cane Lane before it goes back to the candy cane ether. Grab some hot cocoa to go, and drive over to this brightly lit West Allis neighborhood. You’ll enter to find a winter wonderland with candy-cane wrapped trees, and over 300 houses full of festive holiday lights. You can drive or walk through. Don’t forget to leave a donation for the MACC fund!

15. Cool Fool Kite Festival (Free!)

Jan. 1, 2021

Veterans Park, 1010 N Lincoln Memorial Dr, Milwaukee, WI, 53202


Soar into the New Year at the Cool Fool Kite Festival, hosted by Gift of Wings. This family-friendly event takes place every New Year’s Day at Veterans Park along Milwaukee’s downtown lakefront. Bring your own kite or purchase one from Gift of Wings, the store onsite. Lessons and demonstrations in ice sculpting will also take place, as well as horse and buggy rides. Free coffee and hot chocolate are provided at the event to help you keep warm.

16. MPM Community of Curiosity (Free!)


Every month, the Milwaukee Public Museum is bringing you new videos, activities, and information about a beloved exhibit. Check it out!

17. Imagination Station (Free!)

100 E Forest St, Oconomowoc, WI 53066


Imagination Station is huge, universally accessible playground in Oconomowoc. It is located in Roosevelt Park and features rubberized surfacing, therapeutic swings, multi-sensory activity structures, musical components, one entrance and exit for added safety, and more!

18. Christmas at the Zoo

Shalom Wildlife Zoo, West Bend


Photo: Instagram, @briankramp

In the warmth of your own car, drive slow, relax and enjoy the wildlife and the unique holiday displays and decorations. The entire zoo is lit up with special LED lighting for the night time drive-thru. Wildlife viewing is good day or night.

19. Tubing at Wilmot Mountain

11931 Fox River Rd, Wilmot, WI 53192


Grab a tube and let gravity do the rest! You can ski, snowboard, and more at Wilmot Mountain.

20. First Stage's ChristmasTown, now streaming (Free!)

Free to stream on YouTube!

When the folks at Christmastown get the news that First Stage won’t be able to share Rudolph’s story on stage for audiences this season, the Misfit Toys, the Elves and Sam the Snowman decide to come to Milwaukee to help out—sure that they can help First Stage find a way to spread some holiday cheer. Incorporating some of the beloved songs from the show, the special shares their journey from their misadventures around the office and the shops to their discovery of the world of First Stage and Milwaukee to their efforts to cheer Milwaukee’s young people and their families. At a time when we need it more than ever, First Stage offers this gift to the community—filled with music, humor and a healthy dose of holiday magic. For families and audiences of all ages.

21. Snowshoeing (Free + Snowshoe Rental)

If you can walk, you can snowshoe! We rounded up a list of places that are great for snowshoeing with kids. Don't have snowshoes? You can borrow from the Urban Ecology Center if you're a member.

22. “Community Spirit Park” at Cathedral Square Park (Free!)


Photo: Instagram, @bauerbach24

Through the end of 2020 only! Over 100 evergreens have sprung up on the square. Wind your way through the forest of trees and pay close attention to each tree’s décor. More than 50 area schools and businesses share their wish for the season with handmade ornaments and garlands. Plus, check out the park’s Singing Tree, which blinks to singing, music and clapping in real time.

23. Shully's Cooking Kits


Order a cooking kit from Shully's Cuisine and Events to create a culinary masterpiece in your very own kitchen. There's a Sprinkle Cupcake Mix, Monster Cookie Making Kit, and more! Their cooking kits come with all non-perishable ingredients, the full recipe, instructions, and a video to follow along with.

24. Curbside Pickup at any Milwaukee Public Library (Free!)


If there were ever a time to check out dozens and dozens of library books, it's now. All locations are now offering curbside pickup only. You can reserve your books online or call the library.

25. Mequon Nature Preserve (Free!)

8200 W County Line Rd, Mequon, WI 53097


Photo: Instagram, @emilygracewat

Mequon Nature Preserve, rests on over 444 acres, and offers five miles of trails, an observation tower, and an observation platform.

There are three parking lots to start from, like a choose-your-own-adventure book. To climb the observation tower, park in the parking lot on Swan Rd. and follow the trail around Pat's Pond. For good wildlife watching, park near the Pieper Power Education Center, and find the Observation Platform along the Streich Family Wetlands.

There's also a new natural playground right next to the main building!

26. See the Hoan Bridge lit up (Free!)


Photo: Instagram, @natevomhof

Have you seen the Hoan Bridge since it's been lit up by Light The Hoan? You'll definitely want to check it the next time you're downtown!

27. Harbor View Plaza (Free!)

Great Lakes Research Facility, 600 E Greenfield Ave, Milwaukee, WI 53204


📸 @kristinemarie

Check out the play area and tower at Harbor View Plaza. It's all decked out at this time of year!

28. Mural Tour (Free!)

Photo: Instagram, @daisyhead111

Buckle your seatbelts and check out the custom MKE With Kids Mural Tour! You'll find ten murals that will make you proud to be from Milwaukee, including this leopard on the East Side.

29. “Polar Plaza" at Zeidler Union Square (Free!)

301 W Michigan St, Milwaukee, WI 53203


The small downtown park has been transformed for the holiday season! You can a snap a photo in the Season’s Greetings frame, take a selfie in the giant Santa chair, stand inside a sparkling ornament, and see the flickering fireplace.

30. Sledding (Free!)

Hit your favorite sledding hill, or switch up your regular routine! We have a comprehensive list of the best sledding hills around. Check it out!

31. Lights on Glen Cove (Free!)

Off Janesville and Glen Cove Ct. in Muskego, WI www.facebook.com/lightsonglencove/ Marvel at over 35,000 LED lights synchronized to holiday music from 87.9 FM. The lights run every night starting at 5:00 p.m. and running through 9:00 p.m. on weekdays and 10:00 p.m. on weekends. Check the website before you go to make sure it is still running. This is a private residence.

32. Tubing at Sunburst

8355 Prospect Dr., Kewaskum, WI 53040


Just 30 minutes northwest of Milwaukee, Sunburst offers skiing, snowboarding, and tubing in three terrain parks. Their claim to fame is that it is the world’s largest tubing park with over 45 lanes. It was even recognized by USA Today as one of the top ten tubing parks in the entire country.

After a long day on the slopes, you’ll appreciate their fresh food cafe serving up artisan sandwiches and salads, plus Starbuck’s coffee and espresso drinks to help you warm up.

33. Winter Adventure Days at Urban Ecology Center


School is out and it’s time to play! Join the Urban Ecology Center for a fun, active day of playing in the park. You'll take a look at what makes Wisconsin Winters special through crafts, games and so much more. Bring your mask and prepare for an adventure!

34. Kids2Kids Christmas Wonderland

Corner of Highway 60 and Cheyenne at 1150 Cheyenne Avenue, Grafton, Wisconsin. November 27, 2020 – December 31, 2020 (closed on Christmas Eve/Day) 6:00 pm – 9:00 pm Sunday – Thursday, 6:00 pm – 10:00 pm Friday & Saturday Website Kapco’s Kids2Kids Christmas Wonderland is Wisconsin’s ultimate drive-thru holiday experience. Guests of all ages will enjoy millions of lights, two mesmerizing light tunnels, hundreds of inflatables and holiday décor pieces, a live nativity scene. Proceeds from Kapco’s Kids2Kids Christmas Wonderland are utilized to provide new toys to children in need and facing adversity. All guests are encouraged to bring a new, unwrapped toy(s) that will be contributed to a child in need in our community.

35. Skiing / Snowboarding

As long as your child is stable on their legs, they can begin to learn to ski! (Snowboarding starts later around 6 or 7.) Here is a list of nearby places you can ski and snowboard.

36. Wehr Nature Center Waterfall Hike

9701 W College Ave, Franklin, WI 53132


Photo: Instagram, @rileyjgarcia

Yep, this waterfall is right here in Milwaukee County. You’ll find it at Wehr Nature Center in Franklin. Take the Lake Loop, which runs along the shoreline of Mallard Lake and right to this waterfall into the Root River.

You can also explore the short and flat "Family Friendly Trail" which will take you through beautiful woodlands. You'll see lots of birds, and you may even come face to face with a wild turkey.⠀

37. Day Trip Idea: Bay Beach Wildlife Sanctuary (Free!)


The Bay Beach Wildlife Sanctuary in Green Bay is open every day for hiking and wildlife viewing - and it's free! If you're in the Green Bay area, you can also check out Wequiock Falls, a waterfall that actually freezes in the winter!

38. Possibility Playground (Free!)

554 N Lake St Port, Port Washington, WI 53074


Possibility Playground is a huge playground that blends the line between learning, therapy and playtime. It sits in Upper Lake Park in Port Washington with a beautiful view of Lake Michigan. You can enjoy the charming downtown of Port Washington and visit the marina or lighthouse while you're there.

39. Winter Wonders at Boerner Botanical Gardens

Open nightly 5:00 p.m. – 10:00 p.m. November 20, 2020 – January 3, 2021 Closed Christmas Eve & New Year's Eve $25/carload Website

Gather family and friends for a spectacular drive-through holiday lights with over one million lights! There's also a new mini drive-in theater. (First come, first serve.) Enjoy a variety of light displays throughout Whitnall Park from the comfort of your car as you drive alongside magnificent forest scenes and whimsical holiday fun.

40. Day Trip Idea: Henry Vilas Zoo (Free!)

702 S. Randall Ave., Madison, WI 53715

Visit Page

This is a 28-acre free public zoo in Madison, Wisconsin. Owned by the city of Madison, the zoo charges no admission or parking fees. It receives over 750,000 visitors annually. The zoo houses an African lion, chimpanzees, a red panda and more!

41. Horse-drawn Sleigh Rides at Roden Barnyard

5545 County Rd Y, West Bend, WI 53095


42. Milwaukee Art Museum Art Videos (Free!)


Bring the creativity of the Kohl's Art studio into your home by exploring original art-making videos provided by the Milwaukee Art Museum.

43. “Tinsel Town Express” at Pere Marquette Park (Free!)

900 N Plankinton Ave, Milwaukee, WI 53203


Families are cleared for landing at this riverside park. A scene from the North Pole’s depot, this delightful display boasts animated sculptures of the elves shipping packages by air and rail. Don’t miss the parachuting elf or Santa departing by helicopter! It’s a panorama designed for the young and young at heart.

44. Lake Park Hike (Free!)

3233 E. Kenwood Boulevard

Photo: Instagram, @mymkepics

Truly beautiful in any season, the paved winding paths of historic Lake Park will bring you gorgeous lake vistas, rocky ravines, impressive statues, and the charming North Point Lighthouse.

45. Retzer Nature Center (Free!)

S14 W28167 Madison St, Waukesha, WI 53188


Photo: Instagram, @dougrussellimages

Even for the littlest feet, Retzer Nature Center's “Adventure Trail” is filled with majestic pines, picnic tables, and is very short. You can also explore “Vista Trail” where you’ll get a good view of Waukesha, and the “Nature Trail” where there are boardwalks and babbling brooks. There is also a nature center that is open. Masks are required.⠀

46. Winter Wonderland in the Garden District (Free!)

Through January 6th, nightly at dusk 6th & Howard in Milwaukee, WI Website

Photo: Instagram, @johnnymarsz

It’s Winter Wonderland at the Garden District Community Garden at 6th and Howard in Milwaukee. There is no fee, and you can walk through or drive by at any time. It runs through January 6th.

47. Schlitz Audubon Nature Center Hike

1111 E Brown Deer Rd, Bayside, WI 53217


Mystery Lake in winter is magical! It’s a short hike from the Nature Center at Schlitz Audubon Nature Center, but bring a map because it can be tricky to find your first time. Schlitz Audubon Nature Centeris now taking trail reservations on their website.

48. Giant Hot Cocoa at The Corners of Brookfield (Free!)

20111 W Bluemound Rd, Brookfield, WI 53045


There’s a brand new lights display at The Corners of Brookfield! It’s a multi-sensory, 15-foot tall walk-through hot cocoa mug, with 18,000 LED lights and chocolate-scented fog. There’s also a 40-foot immersive lights tunnel running along Market Square adorned with 10,000 color-changing LED lights. They are free to visit, and make for great photo opps.

49. BMO Harris Bank Window Display (Free!)

Nov. 30 - Jan. 4 at 770-790 N. Water St.

“Welcome to Kandy Korners,” will be a holiday window display that harkens back to the department store window displays of the past and will feature a full city block of holiday magic. This is the 48th year that the bank has offered this wonderful event as its traditional holiday gift to the community. The whimsical arrangement will be illuminated so passersby can view it even when it is dark outside. The bank’s treasured collection of life-sized Steiff animals will be displayed in elaborately designed vignettes, sharing the imaginative tales of playful adventures, charming scenery and the sweetest memories. In conjunction with the holiday display, BMO Harris will donate $30,000 to Feeding America Eastern Wisconsin to help feed Milwaukee-area families throughout the holiday season.

50. Holiday Cooking With Kids


Have you checked out Milwaukee's very own food blogger and cook book author, Philia Kelnhofer? Her website sweetphi.com is packed with seasonal ideas that your kids will love, including a hot cocoa recipe, sugar cookies that won't lose their shape, and iced Bailey's coffee for the adults in the house.

***Winter Break Giveaway***

Tag us on Instagram in your photos of your family doing any of the ideas listed below. You'll automatically be entered to win a Wisconsin Winter Survival Gift Package that includes a sled, gourmet hot cocoa, and surprises from our favorite local businesses.

Unlimited entries!

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