10 Magical Holiday Experiences For Milwaukee-Area Kids (2021)

Milwaukee is about to get very merry! We found ten unique holiday experiences and events that you’ll definitely want to know about this year.

PLUS, check out our 2021 Holiday Guide for info on local holiday lights displays, Bayshore’s Season to Sparkle, Santa mailboxes and meeting places, toy stores and sleigh rides.


Download the Vroom App to add learning to mealtime, bathtime, bedtime, or anytime with 1,000+ fun, free activities.

1. Christmas in the Ward

Catalano Square, Milwaukee, WI 53202
Friday, December 3, 2021, 5:30-8:30 p.m.

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Photo Credit:Cindy Kennedy-Lesky, historicthirdward.org

Each Christmas, you’ll find a magical tree lighting in Catalano Square (which is actually a triangle shape – go figure), live entertainment, actual chestnuts roasting on an open fire, costumed characters, a fireworks show over the Milwaukee River, and more.

You can visit with Santa in Jolly’s Outdoor Gingerbread House, and meet live reindeer with Mrs. Claus. Santa’s elves will be on hand to answer questions like “Do reindeer really fly?” and “Is Rudolph’s nose really red?”

Refreshment options include festive fare from Third Ward restaurants and food trucks, hot cocoa, and a cookie sale to benefit Ronald McDonald House Charities. Adults, don’t miss the “cocoa cocktails” and local brewery offerings.

2. Home for the Holidays

Old World Wisconsin, W372 S9727 Hwy 67, Eagle, WI 53119
Saturdays and Sundays, December 4-19, 2021, 10 a.m.-4 p.m.

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Discover the vibrant holiday traditions brought to Wisconsin by our immigrant ancestors, and create your own holiday memories at Old World Wisconsin. Stroll through the Crossroads Village, decked in holiday greenery and full of homes and shops bustling with holiday preparations. Explore how a rich mosaic of ethnic traditions continues to be part of our contemporary celebrations and learn the stories behind them.

This event is sponsored by the Old World Foundation. Advanced tickets are required and ticket sales end at noon the day before each event date.

3. CP Holiday Train

*** This event will be virtual in 2021 ***


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The CP Holiday Train will be a virtual event again this year. In keeping with the CP Holiday Train tradition of live music, CP is planning a virtual benefit concert (more info to come soon). Despite the challenges of COVID-19, the much-loved program continues to serve as a beacon in the fight against hunger.


Since its inception in 1999, the Canadian Pacific (CP) Holiday Train has raised $19.4 million and collected 4.9 million pounds of food for community food banks along CP’s network.

The Holiday Train is about 1,000 feet in length with 14 brightly decorated rail cars. Each car is decorated with hundreds of thousands of technology-leading LED lights and holiday designs.

At various scheduled stops in the Milwaukee area, the illuminated train arrives and pulls to a safe stop in front of the crowd. Then the stage door lowers and the live performances of holiday-themed songs begin. There is also a brief presentation with local food bank officials and dignitaries. Once the band plays its farewell song, the stage door closes, and the train heads off to the next stop. Each stop lasts about 30 minutes.

Each event is completely free, and attendees are encouraged to bring monetary or healthy food bank donations to help alleviate hunger in their own local community.

4. The Domes Holiday Show

Mitchell Park Domes, 524 S. Layton Blvd., Milwaukee, WI 53215
Nov. 20, 2021 – Jan. 3, 2022

Santa has been known to make the occasional appearance at this holiday floral show! You’ll see holiday decorations galore, as well as horticultural holiday staples such as pointsettias, amaryllis, single stem white mums (resembling snow balls), snow white pop mums and cycalmen.  Among the classics, you will also see some non-traditional color, such as bright pink poinsettias and lime green amaryllis.

5. The Nutcracker (Milwaukee Ballet)

Marcus Performing Arts Center, 929 N Water St, Milwaukee, WI 53202
Dec. 10 – 26, 2021 (various showtimes)

Shake off the winter chill and gather again with friends and family for Milwaukee’s annual holiday tradition. More than 150 dancers from around the world create a winter wonderland in this timeless story. Listen to the Milwaukee Ballet Orchestra play Tchaikovsky’s iconic score during “Dance of the Sugar Plum Fairy,” “Waltz of the Flowers,” and “March of The Nutcracker” and more. The stunning visual display features elaborate sets, lavish period costumes, special effects, and even magic tricks! Children will also love seeing the small students of Milwaukee Ballet School & Academy dancing onstage with the professional Company. 

6. Deck the Streets of Old Milwaukee

Milwaukee Public Museum, 800 W Wells St, Milwaukee, WI 53233
Dates TBD

The Streets of Old Milwaukee is one of the most popular exhibits at the Milwaukee Public Museum. During the holiday season, it’s decked out in holiday splendor. Peek into some of your favorite turn-of-the-century storefronts adorned in traditional seasonal flair. Parade past exteriors garnished with the Victorian-era wreaths, ribbons, garland, holly, bell pulls and more!


Download the Vroom App to add learning to mealtime, bathtime, bedtime, or anytime with 1,000+ fun, free activities.

7. A Charlie Brown Christmas by First Stage

The Marcus Center’s Todd Wehr Theater, 929 N. Water St., Milwaukee, WI 53202
Nov. 20-Dec. 26, 2021 (select dates and showtimes)

Come home for the holidays as First Stage brings this treasured holiday classic to life. Join Charlie Brown, Snoopy and the rest of the Peanuts gang as they learn the true meaning of Christmas. The live play production features 11 young performers in two different casts. Performance runtime is approximately 60 minutes, with no intermission. Recommended for families with kids ages 4 and up. Tickets start at $24 and can be purchased in person at the Marcus Center Box Office at 929 N. Water Street, by phone at (414) 273-7206 or online at firststage.org

8. MATC Parade of Gingerbread Houses

Milwaukee Public Market, 400 N. Water St., Milwaukee, WI 53202
Dates TBD

Marvel at over 40 festive and intricate gingerbread houses created by MATC students. The public is encouraged to view and bid on the lovely houses. You can vote for your favorite, too! Proceeds from silent auctions for each house will be used to offer scholarships to students in baking and pastry arts programs through the MATC Foundation, Inc. More details to come soon!

9. Lake Geneva Santa Cruise

1 Liechty Drive, Williams Bay, WI 53191 (departs from Gage Marine/Pier 290 Restaurant)
Wednesday-Sunday, Nov. 26-Dec. 30, 2021 (no departures on Dec. 24-25)

Embark on a magical Christmas boat cruise to Santa’s Hideaway! During this 40-minute lake tour aboard Lake Geneva Cruise Line’s historic boats (enclosed, heated and decked out with twinkling lights), passengers hear the story of Santa’s summer in Lake Geneva and enjoy light displays along the shoreline. The boat comes to a stop right outside Santa’s Hideaway, where Santa himself reads the names of the children on board who are on his “Nice List.”

Before boarding, be sure to walk through the Santa Cause “Charities of Christmas Tree Festival.” This indoor winter wonderland includes eight individually decorated trees, as well as a cash bar.

10. Christmas Trains [SOLD OUT]

East Troy Depot, 2002 Church Street, East Troy, Wis.
Saturdays and Sundays, Nov. 27-Dec. 19, 2021

*** All Christmas Trains are sold out for 2021. ***

The East Troy Railroad’s Christmas Day Train is a magical ride that will take you from the East Troy Depot to Santa’s workshop located at the Elegant Farmer. There children can visit Santa and take a photo with the jolly elf himself! Online advance reservations are required.

The total experience is two hours in duration, consisting of 30 minutes on the train to the Elegant Farmer, 1 hour at the Elegant Farmer, and a 30 minute train ride back to the East Troy Depot. The trolleys are heated, and bathrooms are available in the East Troy Depot.

Other Christmas Trains include a Parade Train and the ever-popular Santa’s Special Night Trains.

There’s more!

Check out our 2021 Holiday Fun Guide for:

Holiday Lights Displays
Bayshore’s Season to Sparkle
Santa’s Mailboxes
Places to Meet Santa
Local Toy Stores
Sleigh Rides

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