Christmas in the Ward

11 Magical Holiday Experiences Your Kid Will Love (2022)

Canadian Pacific CP Holiday Train Milwaukee Wisconsin

Milwaukee is about to get very merry! We found some unique holiday experiences and events that are sure to get the whole family into the holiday spirit. These are some of the best places to raise some holiday cheer!

1. Christmas in the Ward

Catalano Square, Milwaukee, WI 53202
Friday, December 2, 2022, 5:30-8:30 p.m.
Admission: FREE

Christmas in the Ward Third Ward Milwaukee Wisconsin

Each Christmas season, you’ll find a magical tree lighting in Catalano Square (which is actually a triangle shape – go figure), live music, costumed characters, a fireworks show over the Milwaukee River, and more.

You can visit with Santa Claus in Jolly’s Outdoor Gingerbread House (suggested $5 donation to Ronald McDonald House Charities), 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 Historic Third Ward restaurants and food trucks, hot chocolate, and a cookie sale to benefit Ronald McDonald House Charities. Adults, don’t miss the “hot cocoa cocktails,” local brewery offerings, and — new for this year — mulled wine, courtesy of Cafe Benelux.

2. Home for the Holidays (Old World Wisconsin)

W372 S9727 Hwy 67, Eagle, WI 53119
December 3-4, 10-11, 2022, 10 a.m.-3 p.m.
Admission: Adults/Seniors $19.99; Children 5-12 $13.99; Under 5 FREE

This image has an empty alt attribute; its file name is Home-for-the-Holidays.png

Stroll through the site’s Crossroads Village, decked in holiday greenery, full of festive stories and merry memories. Explore a rich mosaic of ethnic traditions and discover how they continue to be part of our modern celebrations. Experience how holidays like Jueltomte, Boxing Day, and Hanukkah bring communities together.

Old World Wisconsin is the perfect spot to meet friends and family from across the region to enjoy a day of warmth and discovery as you create your own holiday traditions. Sights, sounds, smells, and tastes will make history come to life as we connect in new ways.

3. CP Holiday Train

Various locations
Friday, December 9, 2022, 4:15-7:15 p.m.
Admission: FREE (suggested donation of cash or nonperishable food items for local food banks)

Canadian Pacific CP Holiday Train

After a two-year hiatus and being only a virtual experience last year due to COVID-19, the Canadian Pacific (CP) Holiday Train returns to the rails for 2022! It’ll be rolling through the Milwaukee area on Friday, December 9, 2022, making stops in Wauwatosa, Hartland and Oconomowoc.

Since its inception in 1999, the CP Holiday Train has raised more than $21 million and collected more than 5 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 nonperishable food bank donations to help alleviate hunger in their own local community.

Get the 2022 CP Holiday Train schedule >>

4. The Domes Holiday Show: Calm & Bright

Mitchell Park Domes, 524 S. Layton Blvd., Milwaukee, WI 53215
Nov. 19, 2022-Jan. 3, 2023
Admission: $5-$8 (Members and Children 2 and under get in FREE)

Santa has been known to make the occasional appearance at this holiday floral show! Gather your family in the warm glow of elegance and the timeless beauty of hundreds of velvety poinsettias. Capture photos of lasting memories and reunite in the spirit of the holidays.

You’ll see holiday decorations galore, as well as horticultural holiday staples. Besides poinsettias, you may also find 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
December 10-24, 2022 (various showtimes)
Admission: $46-$152

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: December 3-31, 2022
Admission: Adults $22, Seniors/Military/Students $18, Youth 4-13 $16, Members and Children 3 and Under FREE

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 Victorian-era wreaths, ribbons, garland, holly, bell pulls and more!

On Saturdays at 11 a.m., learn how the holiday traditions that were brought by European immigrants to Milwaukee blended together to create our modern celebrations.

7. Rudolph the Red-Nosed Reindeer the Musical (First Stage)

The Marcus Center’s Todd Wehr Theater, 929 N. Water St., Milwaukee, WI 53202
Nov. 25-Dec. 24, 2022 (select dates and showtimes)
Admission: $28.50

First Stage Rudolph the Red-Nosed Reindeer The Musical

The beloved animated TV classic “Rudolph the Red-Nosed Reindeer” soars off the screen and returns to the stage this holiday season. From fleeing the Abominable Snow Monster to saving Christmas, join Rudolph and his friends – Hermey the Elf and Yukon Cornelius – as their adventures teach us that what makes you different can be what makes you special.

Don’t miss this wonderful holiday tradition that speaks to the little misfit in all of us! Suggested for families with young people ages 4 and up.

8. Lake Geneva Santa Cruise

1 Liechty Drive, Williams Bay, WI 53191 (departs from Gage Marine/Pier 290 Restaurant)
Wednesday-Sunday, Nov. 25-Dec. 30, 2022 (no departures on Christmas Eve or Christmas Day)
Admission: $12-$30 (Ages 3 and Under FREE)

Lake Geneva Santa Cruise lake tour Wisconsin

Embark on a magical Christmas boat cruise to Santa’s Hideaway! Along your 40-minute lake tour aboard one of Lake Geneva Cruise Line’s historic boats (enclosed, heated and decked out with Christmas lights), you will be enchanted by lighted displays that unfold the story of your journey.

From the boat, sneak a peek at the shoreline to see Santa’s Hideaway and Santa himself as he reads the names of the children on board who are on his “Nice List.”

Before boarding begins, walk through the Santa Cause “Charities of Christmas Tree Festival.” This indoor winter wonderland includes eight individually decorated trees with a festive atmosphere and a cash bar.

9. Christmas Day Train (East Troy Railroad Museum)

East Troy Depot, 2002 Church St., East Troy, WI 53120
November 26-December 18, 2022 (Saturdays and Sundays)
Admission: Adults $23, Children (ages 3-14) $20, Infants/Toddlers (ages 0-2) $8.50, Members $17

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, and tickets sell out fast!

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.

10. A Dickens of a Village

Historic Downtown Greendale, 6500 Northway, Greendale, WI 53129
Friday, December 2, 2022, 5-9 p.m.
Admission: FREE
Event Page

A Dickens of a Village choir chorus Greendale Wisconsin

Discover the Village Shops decked out for the merriest of seasons, as Historic Downtown Greendale is transformed into a scene from a Dickens novel. Expect more than 100,000 twinkling lights and merchants dressed in Dickens-era costumes.

Write letters to deposit in Santa’s mailbox, and visit the big guy himself. Take a ride on Santa’s sleigh or horse-drawn carriages. Reminisce with holiday entertainment by strolling carolers, bell and chamber choirs, and string instruments. Enjoy a performance of the classic “A Christmas Carol in 12 Minutes.”

Enjoy delicious sweets, treats, and hot beverages. Get a jump on your holiday shopping and take advantage of store specials.

11. Christmas on the Corner

Downtown Port Washington, WI
Saturday, December 3, 2022, 3-7 p.m.
Admission: FREE

Christmas on the Corner holiday parade celebration downtown Port Washington Wisconsin

Port Washington Main Street’s traditional community Christmas celebration is full of festive activities for all ages, including cookie and ornament decorating, a hot cocoa bar, photos with Santa, live reindeer, letters to Santa, horse-drawn carriage rides, and an Elf on the Shelf scavenger hunt.

Stick around for the parade at 6:15 p.m., followed by the only fireworks in Ozaukee County during the month of December.

There’s more!

Experience Gift Ideas
Holiday Light Displays
Santa’s Mailboxes
Places to Meet Santa
Local Toy Stores
Sleigh Rides

Did you like this article?

Check out “101 Best Things to do in Milwaukee With Kids“.

Related Posts