10 Magical Holiday Experiences Your Kid Will Love (2023)

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. Deck the Streets of Old Milwaukee (Milwaukee Public Museum)

800 W. Wells St., Milwaukee, WI 53233
November 10, 2023 – January 21, 2024

Experience the magic of the holiday season inside two of MPM’s most beloved exhibits, Streets of Old Milwaukee and European Village, where the walkthrough turn-of-the-century streetscapes are transformed into holiday wonderlands.

European Village Alive! returns this year on December 8 and 9. Learn about centuries-old holiday traditions from costumed docents. Free with admission.

Learn more >>

2. Christmas in the Ward

Catalano Square, Milwaukee, WI 53202
Friday, December 1, 2023, 5:30-8:30 p.m.
Admission: FREE

Christmas in the Ward Third Ward Milwaukee Wisconsin

At Christmas in the Ward, 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 “Cocoa Cocktails,” local brewery offerings, and mulled wine, courtesy of Cafe Benelux.

See more Christmas Tree Lightings Around Milwaukee >>

3. The Domes Holiday Show: A Holiday Snow Globe

Mitchell Park Domes, 524 S. Layton Blvd., Milwaukee, WI 53215
Nov. 18, 2023-Jan. 7, 2024

Santa has been known to make the occasional appearance at this holiday floral show!

The Mitchell Park Domes presents “A Holiday Snow Globe,” a stunning display of winter beauty for all to experience. 

This holiday season, enjoy the warmth of the Domes amid a field of hundreds of poinsettias, grouped with decorated spruce trees and more seasonal favorites.

Bring your loved ones into a polar paradise of playful animals enjoying the winter season and preparing for the holidays.

4. Lake Geneva Santa Cruise

1 Liechty Drive, Williams Bay, WI 53191 (departs from Gage Marine/Pier 290 Restaurant)
Starts November 24th, 2023 (no departures on Christmas Eve or Christmas Day)

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.”

5. Enchant Christmas

Ballpark Commons in Franklin
Starts November 24th, 2023

Enchant is an immersive experience weaving magic into its every corner. Adventure through The Great Search, a captivating, larger-than-life light maze that is the cornerstone to the Enchant experience.

Wander the Village of tiny storefronts featuring artisan vendors, specialty crafters, and boutiques, indulge in a tasty seasonal treat or delightful beverage, ice skate through a dazzling forest of Christmas lights, visit with Santa in the Enchant Village, and let your little play in Little Elves Play Place.

6. Christmas Day Train (East Troy Railroad Museum)

East Troy Depot, 2002 Church St., East Troy, WI 53120
Start November 25th, 2023 (Saturdays and Sundays)

Note: These tickets typically sell out weeks in advance!

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.

7. CP Holiday Train

Various times and locations
December 3-4, 2023
Admission: FREE (suggested donation of cash or nonperishable food items for local food banks)

Canadian Pacific CP Holiday Train

The Canadian Pacific (CP) and Kansas City Southern (KCS) Holiday Train is back on the tracks this year traveling across the US to put on live concerts and raise money for community food banks.

The train will make a grand entrance at 13 stations in Wisconsin over three days, transforming an ordinary cargo car into a stage overflowing with holiday spirit. All events are free, and guests are encouraged to bring food or cash donations to help local communities in need.

Singers Tenille Townes and Breland will be performing at all Wisconsin stops!

Sunday, December 3, 2023

Sturtevant – 6:45 PM Arrival

Insider Tip: For a snack before the holiday train, stop by Lehmann’s Bakery for a taste of Wisconsin’s official state pastry, Kringle!

Caledonia – 8:05 PM Arrival

Monday, December 4, 2023

Wauwatosa – 4:00 PM Arrival

Insider Tip: Get some holiday shopping done in The Village, Wauwatosa’s walkable historic district brimming with cute shops and eateries.

Hartland – 5:30 PM Arrival

Insider Tip: Spend some quality time with your favorite people before the big event–warm up by the cozy fireplace with a hot cup of joe or tea at Birch & Banyan Coffee in Hartland.

Oconomowoc – 6:40 PM Arrival

Insider Tip: Searching for a place to stay the night and extend the fun all weekend? The Inn at Pine Terrace is a restored Victorian mansion that sits on scenic Fowler Lake, just a ten-minute walk to downtown. Warm up after the holiday train show at the grand outdoor fireplace that overlooks the water.

Watertown – 7:50 PM Arrival

Insider Tip: Swap your snow boots for skates with a visit to the Skate Express Family Roller Rink! Stop by in the afternoon for a few spins around the rink before the holiday train rolls in that evening. And don’t forget to stroll main street and vote for your favorite seasonal display for Watertown’s Window Wonderland.

8. Home for the Holidays (Old World Wisconsin)

W372 S9727 Hwy 67, Eagle, WI 53119
December 2-3, 9-10, 16-17, 2023

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

Stroll through Crossroads Village at Old World Wisconsin, 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.

9. The Nutcracker (Milwaukee Ballet)

Marcus Performing Arts Center, 929 N. Water St., Milwaukee, WI 53202
December 8-26, 2023 (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. 

10. MATC Parade of Gingerbread Houses

Milwaukee Public Market (400 N Water St, Milwaukee, WI 53202)
Dated TBD

From December 1st to December 12th, be a part of a Milwaukee Public Market tradition. Visit intricate and whimsical gingerbread house displays made by the talented students at MATC’s baking program. Vote on the winning house, and place a bid!

The gingerbread houses are located upstairs. Be sure to stop by Santa’s Mailbox and write him a letter. They’ll send it directly to the North Pole! The mailbox is also located upstairs.

More Events:

A Dickens of a Village

Historic Downtown Greendale, 6500 Northway, Greendale, WI 53129
Friday, December 1, 2023
Admission: FREE

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.

Christmas on the Corner

Downtown Port Washington, WI
Saturday, December 2, 2023
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 and fireworks!

There’s more!

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

Did you like this article?

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

About the author

In 2013, Calie Herbst, a former teacher with three little ones, saw a need for a “One Stop Shop” for family fun in Milwaukee. So she founded Milwaukee With Kids. Her goal was to find the best this city has to offer families and share it with other parents. In one place. In 2019, she published "Exploring Milwaukee WIth Kids", a comprehensive Milwaukee travel guide for families and kids. She appears regularly on WISN News, Fox 6's 'Real Milwaukee', B93.3, and Wisconsin Morning News. She has been featured in Medium, the Milwaukee Journal Sentinel, NPR, the Wisconsin Jewish Chronicle, and on CBS 58 News. Calie is available for hosting, moderating and media appearances.

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