8 unique Christmas events for kids

Here are some of our top picks for the most unique and memorable activities for kids and families during the holiday season.

CP Holiday Train

December 2nd and 3rd, 2017

​Don’t miss the festive lights and live excitement of the CP Holiday Train from Montreal, Quebec. Since 1999, the trains have raised more than $13 million and four million pounds of food for communities along its routes.

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 each stop, after the illuminated train arrives and pulls to a safe stop in front of the crowd, the stage door lowers and the live music begins. This year, fans will enjoy performances of holiday themed songs by Terri Clark, Dallas Smith and Kelly Prescott. There will also be 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.

Stops in Southeastern Wisconsin this year are:

Saturday, December 2nd


9900 East Exploration Ct., Amtrak Depot

5:25 p.m. – 6:05 p.m.


433 West St. Paul Avenue, Amtrak Depot

6:50 p.m.0 7:45 PM

Sunday, December 3rd


Harwood Avenue crossing

4:15 p.m. – 5:00 p.m.


Level Crossing at Cottonwood Avenue

5:45 p.m. – 6:30 p.m.


South Main Street railway crossing

6:55 p.m. – 7:25 p.m.


Brandt Quirt Park parking lot (ball diamond), adjacent to track

7:45 p.m. – 8:30 p.m.

Christmas in the Ward

Friday, December 1st & Saturday, December 2nd

Catalano Square

6:05 tree lighting ceremony on Friday

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Each Christmas, you’ll find a magical tree lighting in Catalano Square (which is actually a triangle shape – go figure), live reindeer with Mrs. Claus, actual chestnuts roasting on an open fire, horse drawn carriage rides, costumed characters, hot cocoa, and more. You can visit with Santa in Jolly’s Outdoor Gingerbread House, too. Plus, for the adults, don’t miss their “cocoa cocktails”!

Gingerbread House Display (Free!)

Milwaukee Public Market

400 N. Water St., Milwaukee, WI 53202

(414) 336-1111

December 1st – 13th

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Stop by the second floor of the Milwaukee Public Market from December 1st to December 13th and marvel at over 40 festive and intricate ginger bread 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.

An Old World Christmas

Saturday, December 2, 2017 – Sunday, December 3, 2017 from 10:00 a.m. – 4:00 p.m.

Saturday, December 9th, 2017 – Sunday, December 10, 2017 from 10:00 a.m. – 4:00 p.m.

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Travel back in time and stroll through the 1880’s Crossroads Village decked in homemade holiday greenery, full of homes and shops bustling with historic holiday preparations. Wisconsin’s rich ethnic heritage come to life with holiday preparations, traditional European Christmas characters like Krampus, and horse-drawn bobsled rides around the village.

You’ll see preparations for Christmas Eve and Christmas Day festivities in the late 19th century and encounter figures from Christmas stories, like St. Nicholas, Jultomte, Krampus and of course, Santa Claus. Hear live, traditional, holiday brass carols, join in a Hymn Sing, learn about the origins of the Christmas Tree, and keep warm with cider or a cup of wassail. Enjoy holiday treats, hear old Christmas tale storytelling, decorate the holiday tree, make historic holiday crafts, and watch the blacksmith make winter tools.

For even more holiday cheer, purchase tickets to their scrumptious Old World Holiday Breakfast.

Don’t forget to dress for the weather and avoid strollers if you can (they don’t always work well on the snowy paths and inside small, old buildings).

Christmas Train in East Troy (SOLD OUT!)

East Troy Electric Railroad

Saturdays and Sundays, November 25 to December 17

Price Adults $17.50; Kids 3-14 $15.00; Kids 0-2 $5.00

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Take your family on a magical ride from the East Troy, Wis. depot to Santa’s Workshop, where children visit Santa, enjoy cookies and hot chocolate, and take home a small gift. Trains depart at 9:00am, 10:30am, Noon, 1:30pm and 3:00pm on Saturdays and Sundays Nov. 25 to Dec. 17. Reservations are required.

Sleigh & Sled Rides

Horse-drawn Sleigh Rides at Apple Holler ($$)

5006 S. Sylvania Ave., Sturtevant, WI 53177

(262) 884-7100


The old-fashioned sleigh rides at Apple Holler take you and your family through the snow-covered orchards and 100-year-old hardwoods, while you enjoy the scenery and listen to the clopping of the Amish Haflinger horses pulling you. Aftwewards, you’ll enjoy s’mores around a campfire and a cup of hot cocoa or warm apple cider.

Dog Sled Rides with Door County Sled Dogs ($$)


(414) 967-9677

This non-profit organization is run entirely by volunteers, and their sled team is made up of lovable rescued dogs. They race for charities and offer dog sled rides in Whitnall Park. Rides are usually offered January through February, but they are weather dependent. You’ll get to visit with the dogs, ask questions of their humans, take pictures, and enjoy a dog sled ride on the trail. There is a warming house with concessions and a sledding hill nearby. Check the website or call the Sled Dog Hotline for the most updated details.

Horse-drawn Sleigh Rides at Paradise Ranch ($$$)

2408 Spring Hill Dr., Cedarburg, WI 53012

(262) 825-7500


The sleigh rides at Paradise Ranch are pulled by majestic Percheron horses that take you through forty acres of woods that are decorated with twinkling Christmas lights. The sleigh holds up to 12 people. Afterwards, you can sit around the campfire with s’mores, or enjoy the heated, festive barn and a warm drink.

Cocoa with the Clauses (Free!)

Saturday, December 9th

11:00 a.m. – 2:00 p.m.Cathedral Square Park

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“Straight from the North Pole, Santa and Mrs. Claus will visit Cathedral Square Park, 520 E. Wells St., on Saturday, Dec. 9 from 11 a.m. to 2 p.m. as part of the annual cocoa klatch, Cocoa with the Clauses.

The free outdoor event is a chance for kids to share their wish lists, and for moms and dads to snap a free keepsake photo provided they bring a camera. Elves and other holiday characters will be there, plus DJ Shawna will spin holiday hits. Other free treats include hot cocoa, cookies and face painting.

While the outdoor event is free to attend, a nonperishable food donation for Feeding America Eastern Wisconsin is encouraged.

After visiting with Santa and Mrs. Claus, families are invited to enjoy lunch downtown. Several restaurants near Cathedral Square Park will offer kid-friendly menus at budget-conscious prices, just for the occasion. Menus will be distributed at the event.”

Santa at the North Point Lighthouse Museum

Sunday Dec. 10th and Sunday Dec 17th

1:00 – 4:00 PM


Have your picture taken with Santa in his vintage maritime workshop.

Did you know that Santa uses lighthouses to find your house on Christmas Eve? In fact, he’ll be at The North Point Lighthouse Museum telling you about the legend of Christmas and all about the history of the North Point Lighthouse built in 1888.You can take your own photos with him in his vintage maritime workshop complete with classic toys and ships. The NPLH museum is located at 2650 N. Wahl Ave in Milwaukee’s historic Lake Park.

Admission is $8 for adults • $5 for adults age 65+ with ID • $5 for children age 5-11 • No charge for children age 4 and under. All active and retired Military are free with ID.

Explore more:

Holiday Lights Displays

Christmas parades & tree lightings

Breakfast with Santa

Live Holiday Shows

Shop Local Holiday Guide

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