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Get ready, Milwaukee – this holiday season is packed with unforgettable moments that feel straight out of a storybook.
These aren’t your everyday light displays or Santa photo ops, they’re experiences that immerse your family in the magic of the season. Step aboard festive trains, stroll through historic villages glowing with tradition, and watch timeless holiday stories come alive on stage.
Each one offers that warm holiday magic you’ll remember long after the decorations come down.
Looking for more ways to celebrate? Don’t miss our full Milwaukee Holiday Guide for Families, including guides to the best Holiday Lights & Santa Sightings.
Enchanting Rides & Cruises
1. Lake Geneva Santa Cruise
📍1 Liechty Drive, Williams Bay, WI 53191 (departs from Gage Marine/Pier 290 Restaurant)
Embark on a magical Santa Cruise in Lake Geneva! 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.”
2. East Troy Electric Railroad: Ride to Santa’s Workshop
📍East Troy Depot, 2002 Church St., East Troy, WI 53120
📅 Starts November 28th, 2025
Few holiday experiences capture nostalgia like a ride on the East Troy Electric Railroad. Starting November 28, 2025, families can climb aboard the historic train cars for a festive ride straight to Santa’s Workshop at The Elegant Farmer. Each two-hour round-trip includes a chance to meet Santa, take family photos, and enjoy activities at the workshop. Children even receive a small gift on the way back.
Daytime Christmas Trains run weekends through December 21, while Evening Christmas Trains offer a cozy ride with hot chocolate, cookies, and special touches in the first-class dining cars. Heated cars, restrooms, and free parking make it a comfortable outing for all ages.
Train enthusiasts will love our Train Lovers’ Guide to Milwaukee – packed with museums, rides, and local adventures for kids and families year-round.
3. CP Holiday Train (Free!)
📍December 9-11, 2025
Admission: FREE (suggested donation of cash or nonperishable food items for local food banks
You’ll hear the music before you see it – a fully decked-out train glowing with thousands of lights as it rolls into town, spreading cheer and live music wherever it stops. The Canadian Pacific 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, overflowing with holiday spirit including bright holiday decor and live musical performances.
For even more locomotive adventures, explore our Train Lovers’ Guide to Milwaukee and Beyond — featuring the best year-round train rides, museums, and hidden gems for families.
Holiday Stories Come To Life
4. Home for the Holidays (Old World Wisconsin)
Dates: December 6–7 & 13–14, 2025
Location: Old World Wisconsin, Eagle, WI
Step back in time and see how holiday traditions came to life more than a century ago. Families can explore decorated historic homes, meet 19th-century Santas, and enjoy hands-on crafts, wagon rides, and seasonal treats.
Highlights include:
- Victorian Santa’s Workshop: Watch toy-making demonstrations and drop off letters for Santa.
- Horse-Drawn Wagon Rides: Enjoy a scenic ride through the grounds (extra ticket required).
- Holiday Crafts: Make ornaments, greenery décor, and other keepsakes to take home.
- Julbock Straw Goat Display: Snap a family photo with this Scandinavian holiday symbol.
- Yuletide Characters: Meet friendly and mischievous figures from European folklore.
- Historic Home Celebrations: Visit homes depicting Irish, Finnish, Yankee, and Jewish holiday traditions — from St. Nicholas Day and Hanukkah to St. Lucia’s Festival.
- Live Music: Sing along with the Brass Knuckles quintet performing classic carols throughout the day.
- Warm Drinks at Wittnebel’s Tavern: Stop inside for a cozy break and festive cheer.
- Gingerbread House Contest: Test your creativity in a new build-and-decorate competition inspired by Old World Wisconsin’s historic buildings.
This annual event offers a relaxed, family-friendly way to experience holiday traditions from many cultures, all in one beautiful countryside setting.
5. The Nutcracker (Milwaukee Ballet)
📍Marcus Performing Arts Center, 929 N. Water St., Milwaukee, WI 53202
📅 Various showtimes throughout December
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!
From the swell of the orchestra to the shimmer of snow on stage, it’s Milwaukee’s most enchanting holiday tradition. Children will also love seeing the small students of Milwaukee Ballet School & Academy dancing onstage with the professional Company.
See even more seasonal performances and family-friendly productions in our Guide to Holiday Shows in Milwaukee.
6. Deck the Streets of Old Milwaukee (Milwaukee Public Museum)
📍800 W. Wells St., Milwaukee, WI 53233
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.
Festive Towns & Traditions
7. Christmas in the Ward (Free!)
📍Catalano Square, Milwaukee, WI 53202
📅 Friday, December 5, 2025
Admission: FREE
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.
See even more local tree lighting celebrations in our Milwaukee Christmas Tree Lighting Guide.
8. A Dickens of a Village (Free!)
📍Historic Downtown Greendale, 6500 Northway, Greendale, WI 53129
📅Friday December 5th – 5:00 PM – 9:00 PM
Admission: FREE
Historic Downtown Greendale is transformed into a scene from a Dickens novel. Over 100,000 twinkling lights & merchants dressed in Dickens era costumes. Reminisce to holiday entertainment by strolling carolers, bell and chamber choirs, string instruments and watching a 12-minute version of the Christmas Carol. Write letters to Santa and visit the big guy himself.
Enjoy delicious sweets, treats, and hot beverages. Get a jump on your holiday shopping and take advantage of store specials. Take a ride on Santa’s sleigh or hop on a horse drawn carriage. Visit Gazebo Park to pick up a holiday wreath or tree. Stop at the Library for activities for the kids.
9. Christmas on the Corner (Free!)
📍Downtown Port Washington, WI
Admission: FREE
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!
Holly Jolly Jubilee & Gingerbread Village at Apple Holler (Sturtevant)
📍5006 S Sylvania Ave, Sturtevant, WI 53177
A festive walk-through experience packed with holiday charm. Families can enjoy:
- Elf-led sing-alongs and letters to Santa
- Cookie decorating and ornament crafting
- Warm cider and cozy spots inside the North Pole Barn
- Gingerbread scavenger hunt through a whimsical village
- Candy Cane Express Train Rides
- Mrs. Claus’s Cocoa & Donut Shop
- Campfires & photo ops, including a giant sleigh and the Golden Goat Bridge
Whimsical Displays & Winter Magic
10. MATC Parade of Gingerbread Houses
📍Milwaukee Public Market (400 N Water St, Milwaukee, WI 53202)
📅 2025 Dates Coming Soon
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.
See more festive gingerbread creations across the region in our Gingerbread House Displays & Contests Guide.
11. World’s Tallest Glass Tree Festival
📍 Yerkes Observatory, Williams Bay
📅 December 5–7 & 12–14, 2025
🎟 Kids 12 and under are free; parking is off-site at Williams Bay School with a trolley shuttle to the Observatory.
This beloved holiday festival celebrates glass artistry and the making of the world’s tallest glass tree. Explore the Observatory’s historic Hagenah Rotunda, visit the Big Dome to see the world’s largest refracting telescope, and browse a cozy market filled with handmade gifts, local art, and festive food and drinks. Outside, enjoy live music, chainsaw art, fire pits, and warming tents..
12. The Domes Holiday Show & Late Nights
📍Mitchell Park Domes, 524 S. Layton Blvd., Milwaukee, WI 53215
📅 Nov 22, 2025 – Jan 4, 2026 | Late Nights: Nov 29, Dec 10, Dec 17, Dec 27, open until 8PM
Celebrate the holiday season with a multicultural display at The Domes! This year’s “Holiday Parade” showcases the beauty of diverse traditions, including Advent, Winter Solstice, Christmas, Hanukkah, and Kwanzaa.
Set among beds of vibrant poinsettias in varieties like ‘Red Ribbon,’ ‘Polar Bear,’ and ‘Candy Wintergreen,’ these stationary holiday “floats” create a unique and magical experience for families.
Plus, on select evenings, enjoy the wonder of The Domes after dark, open late for an extra special view of the holiday display.
Whether your family’s favorite holiday magic comes from twinkling lights, a warm cup of cocoa on a winter train, or meeting Santa himself, there’s no shortage of wonder waiting around Milwaukee this season.
Keep the celebration going – explore our other guides for even more festive fun:
- Holiday Light Displays
- Santa’s Mailboxes
- Places to Meet Santa
- Local Toy Stores
- Sleigh Rides
- Breakfast With Santa
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.
