7 Holiday Experiences Your Kids Will Be Amazed By

Milwaukee is about to get very merry. We found seven unique holiday events that you'll definitely want to know about this year.

PLUS, check out our 2019 Holiday Fun Guide for Holiday Lights, Tree Lightings, Christmas Parades & 10 Places You Didn't Know Santa Visited In Milwaukee, and Black Friday Alternatives.

1. CP Holiday Train

Thursday, December 6th & Friday, December 7th, 2018


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. 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:

Monday, December 2nd, 2019


9900 East Exploration Ct., Amtrak Depot

Arrival 6:50 pm

Show 7:00 - 7:30 p.m.


Railway Crossing at County Road G and 5 1/2 Road (Depot Tavern)

Arrival 8:00 pm

Show 8:15 -8:45 pm

Tuesday, December 3rd, 2019


Harwood Avenue crossing

Arrival 4:00 pm

Show 4:15 p.m. - 4:45 p.m.


Level Crossing at Cottonwood Avenue

Arrival 5:30 pm

Show: 5:45 p.m. - 6:15 p.m.


South Main Street railway crossing

Arrival 6:40 pm

Show: 6:45 p.m. - 7:15 p.m.

2. Christmas in the Ward

Friday, December 6th from 5:30 - 8:30 p.m.

Catalano Square


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"!

3. MATC Parade of Gingerbread Houses (Free!)

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

December 7th - 16th, 2019

Visit Website

Stop by the second floor of the Milwaukee Public Market from December 7th to December 16th and marvel at over 40 festive and intricate ginger bread houses created by MATC baking 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.

4. Old World Christmas

December 7-8 & 14-15, 2019 from 10:00 am - 4:00 pm


Move over Santa, Krampus is coming to town! This mischievous holiday creature from Central European folklore is just one of the many traditions that will be explored this December at Old World Wisconsin’s  “An Old World Christmas.”

Guests will immerse themselves in engaging and interactive experiences inspired by holiday customs brought to the state by the diverse cultures that helped shape the traditions many Wisconsin families continue to practice today.

Old World’s 1880s Crossroads Village will be decked in holiday greenery and full of buildings bustling with holiday preparations. Guests can help prepare Vanocka, a traditional braided bread; listen to live music, carols, and hymns; learn about holiday traditions like St. Nicholas and English Boxing Day; enjoy a scenic horse-drawn ride; take a photo in Santa Claus’ Victorian workshop and in front of the largest Yule Goat in North America; and visit with a few of the site’s four-legged residents in the barns. Remember to watch out for Krampus, who will be wandering around the site taking selfies with guests. Hot beverages are available for purchase.).

5. Sleigh 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.

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.

6. Santa's Mailbox

Santa's Mailbox presented by Serving Older Adults and GEICO Local Milwaukee Office November 21 - December 15 Cathedral Square Park


Santa’s elves have been busy building an official mailbox at Cathedral Square Park. Children can drop their letters into Santa’s Mailbox where wish lists will be expedited to the North Pole. 

Best of all, every boy and girl who writes to Santa will receive a personalized letter in return! No postage required. Holiday spirit ensures delivery—just be sure to include your return address.

7. Christkindl Market at Fiserv Forum

November 15 - December 24


The Christkindlmarket Milwaukee is coming back to the Deer District! Don't miss out on 40 days of holiday fun from November 15 - December 24! Visit to experience a traditional German holiday market in the heart of the city, complete with delicious food & drinks, collectibles, and gifts. Free Admission!

There's more!

Check out our 2019 Holiday Fun Guide for:

Holiday Lights

Tree Lightings

Christmas Parades

10 Places You Didn't Know Santa Visited In Milwaukee

Black Friday Alternatives

0 views0 comments


Our *free* weekly newsletter keeps you posted on the best events for kids around town. Happy exploring!