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The holidays are here, and there’s something undeniably magical about holiday trains.
Whether it’s a brightly lit locomotive rolling into town or a miniature model train weaving through a festive display, trains are a timeless symbol of holiday cheer.
From live performances on real trains to intricate toy train displays, here’s your guide to the best holiday train experiences for families around Milwaukee this season.
1. The Canadian Pacific Holiday Train
Dates: December 9-11, 2025
Locations: Sturtevant, Caledonia, Wauwatosa, Hartland, Oconomowoc, and more
This dazzling train, adorned with thousands of twinkling lights, makes 13 stops in Wisconsin this year. There will be live performances and free festivities. Bring non-perishable food donations to support local food banks and enjoy the festive music and atmosphere.
2. East Troy Railroad Christmas Trains
Dates: Starts November 28th, 2025
Location: East Troy Depot, East Troy, WI
Hop aboard the historic East Troy Railroad for a cozy journey to Santa’s Workshop at the Elegant Farmer. Kids can meet Santa, receive a special gift, and enjoy the beautifully decorated workshop. The train cars are warm and comfortable, making it a perfect way to embrace the winter season without the chill.
🎟️ Tickets sell out quickly—book your ride now!
3. Holidays on The Hop
Dates: December 7, 14 & 21, 2025
Location: The Hop Streetcar, Milwaukee
Milwaukee’s streetcar gets a holiday makeover with live music, cookies, and festive décor. Enjoy holiday-themed performances by local artists like the Milwaukee Choristers and JL Russell Jazz Trio while you ride through the city. It’s a unique, urban holiday train experience perfect for families looking to explore Milwaukee in a festive way.
👉 Learn more about “Holidays on The Hop”
Apple Holler’s Candy Cane Express Train
Hop aboard the Candy Cane Express at Apple Holler in Sturtevant! This holiday-themed train ride takes families to the North Pole Barn for a festive experience, including a live holiday show, cookie decorating, warm cider, and a visit with Santa. It’s a great way to combine holiday trains with seasonal fun for kids.
Save the Date: The Domes’ Annual Train Show
Train enthusiasts, mark your calendars! The beloved Annual Train Show at Milwaukee’s Mitchell Park Domes will return in 2025, running from January 18 through April 6.
Each year, the Show Dome transforms into a magical world featuring 600 feet of miniature train tracks weaving through lush, colorful plantings. From tiny toy towns to whimsical displays, the exhibit captures the hearts of kids and adults alike.
👉 Read about last year’s Train Show for a glimpse of the enchanting displays you can expect!
More Holiday Magic
From Santa meet-and-greets to light displays, Milwaukee has plenty of ways to keep the holiday spirit rolling.
📌 Explore more in our Holiday Fun Guide or dive into our articles about the Canadian Pacific Holiday Train and the East Troy Railroad for detailed tips on making the most of your holiday train adventures.
What’s Your Favorite Holiday Train Experience? We’d love to hear about your family’s favorite holiday train traditions. Email us at hello@mkewithkids.com, and we may feature your idea!
Calie Herbst, Editor-in-Chief of Milwaukee With Kids, has spent over a decade combining her experiences as a parent of three to create a hub for Milwaukee’s family adventures.
Her decade-long teaching career in Milwaukee Public Schools and academic background, including a Master’s in Teaching from Marquette University and dual B.A.s in Sociology and Spanish from the University of Wisconsin – Madison, fuel her passion for inclusive and engaging family content.
Calie is also a recognized voice in local media, contributing to WISN Channel 12 News, WTMJ Wisconsin Morning News, Fox 6’s Real Milwaukee, and B93.3.
Discover more about Calie’s journey and editorial approach on her About Page and Editorial Policy Page.
