2025 Milwaukee Holiday Events and Festivals
A Cedarburg Christmas – Cedarburg
November 21st thru Christmas
Downtown Cedarburg
Stroll through beautiful downtown Cedarburg, where centuries-old limestone buildings house enticing shops, shopkeepers adorn their storefronts with twinkling lights and quaint displays. Visit Santa in his workshop, run in Santa’s Dash Away 5K on December 14th, enjoy the numerous craft fairs and art exhibits, or take a free trolley ride!
Milwaukee Holiday Lights Festival – Milwaukee
November 20 – January 1
Downtown Milwaukee
MKE it back to explore the lights and sights around Downtown Milwaukee. Ooh and ahh at the winter wonderland throughout Downtown Milwaukee by jumping on the Jingle Bus. Enjoy the Ornament Trail where larger than life ornaments have taken over Wisconsin Avenue. Each ornament has been hand-painted by local artists or national artists with Milwaukee ties. And don’t forget to bring your letter to drop off at Santa’s mailbox!
Milwaukee Holiday Lights Festival Website
Holiday Folk Fair – West Allis
November 21 – November 23
State Fair Exposition Center
Holiday Folk Fair International, America’s premier multicultural festival and a program of the International Institute of Wisconsin, celebrates the cultural heritage of the people living in southeastern Wisconsin. You can explore the ways music, food, dance, and art weave together a message of welcome.
Jellystone Park’s Christmas Carnival of Lights – Caledonia
November 22 – January 31
Yogi Bear’s Jellystone Park
Relax in the comfort of your own vehicle as you wind your way through our campground’s winter wonderland, book your seat on Santa’s GIANT Sleigh or take a ride in our Golf Cart Holiday Train for a unique experience. Enjoy Christmas in the country with lights on all sides that are high above in the trees and one-of-a-kind hand-crafted displays. Reservations required.
Jellystone Park’s Christmas Carnival of Lights Website
German Christmas Market – Oconomowoc
November 26 – 30
The German Christmas Market has something for everyone regardless of age and tastes. It’s Europe meets Wisconsin mixed with holiday merriment. Come for an hour and stay for the day and night! You’ll love the sights and smells of a warm, inviting German Christmas complete with warm roasted nuts, authentic German beer and incredible gifts you won’t find in any mall or retail store!
The Pfister Annual Tree Lighting Ceremony – Milwaukee
November 28
Pfister Hotel
Join us at The Pfister Hotel for our signature Holiday tradition as Santa lights the spectacular lobby tree. Sip warm drinks and nibble on a holiday treat while you enjoy the fun. To help those in need within our community, we will be collecting food for Hunger Task Force. To contribute, please bring a non-perishable food item.
Add a little extra cheer to your evening and head up to Blu after the tree lighting for some festive holiday cocktails!
The Pfister Annual Tree Lighting Ceremony Website
Country Christmas – Pewaukee
Walking nights – Nov. 14-16 & Nov. 21-23, 26
Bike nights – Nov. 24-25
Drive through nights – Nov. 28 – Dec. 2 & Dec. 4 – Jan. 3
Ingleside Hotel
Nestled in the heart of Southeastern Wisconsin is a holiday destination steeped in festive tradition. Each year, The Ingleside Hotel is transformed into a winter wonderland called Country Christmas. Admission to Wisconsin’s largest drive through Christmas lights display includes a trip through the Country Christmas Trail and entrance to two buildings located at the end of the trail, Christmas Village and The Streets of Bethlehem.
Milwaukee Makers Market – Milwaukee
December 21, 10:00AM-4:00PM
Discovery World
Explore the market, have fun, meet amazing artists and artisans, shop, and support the independent maker spirit in Milwaukee. They’ll transform the promenade into a stunning and lively indoor market. Meet Milwaukee jewelry makers, artists, designers, and other skilled artisans. Shop one-of-a-kind, locally-made products including ceramics, women’s clothing, leather goods, candles, and more. The Market is free, but General Admission applies if visiting the entire museum.
A Christmas Carol – Milwaukee
November 25 – December 24
The Pabst Theater
A Christmas Carol is one of the best-known and loved stories in the English language. During the course of one memorable Christmas Eve, the ghosts of Christmas Past, Present and Future help Scrooge discover that it is never too late to change his miserly ways. Enchanting music, dance, costumes, scenery and special effects will once again fill the theater to tell this timeless tale of love, hope and redemption.
Nuncrackers: The Nunsense Chirstmas Musical – Elm Grove
December 4 – December 21
Sunset Playhouse
The Little Sisters of Hoboken are here to make your holiday season merry and bright! Enjoy the hilarity that ensues when the Reverend Mother decides to tape a Christmas TV special in the newly built convent basement. This musical is filled with wacky humor, your favorite carols, and a “Secret Santa” sequence featuring audience participation.
Christkindlmarkt – West Allis
December 5 – December 6
West Allis Farmers Market
Deer District Holiday Market – Milwaukee
November 21-30
Deer District
Deer District’s Holiday Market will showcase a curated lineup of local vendors, holiday-themed photo opportunities and seasonal food and beverage specials from Deer District establishments. Also, stop by to send a letter to Santa with Santa’s Mailbox! The market is free to attend and will be open daily, excluding Nov. 27, when it will be closed to observe Thanksgiving Day.
Christmas in the Ward – Milwaukee
December 5, 5:30 – 8:30 pm, Catalano Square
Shop the Ward – Nov. 29 – Dec. 23
Experience an old-fashioned tree lighting ceremony in Catalano Square (138 N Broadway). Enjoy music, live reindeer, hot cocoa, pictures with Santa, and more.
Midnight Magic – Mukwonago
December 6
Old fashioned Christmas celebration. A town-wide festival featuring indoor crafter marketplace, shopping, parade, fireworks, pictures with Santa, holiday entertainment, horse-drawn carriage rides, and more! Please be prepared to follow social distancing requirements.
Annual West Allis Christmas Parade – West Allis
December 6
The West Allis Christmas Parade is an annual holiday tradition and the premier night-time Christmas parade in Southeast Wisconsin! Enjoy marching bands and live performers, creative floats and vintage vehicles; meet elves, cartoon characters; and of course, wave to Santa Claus himself at the end of the parade!
Annual West Allis Christmas Parade Website
An Old World Christmas – Eagle
December 6-7, 13-14
Old World Wisconsin
Stroll through the 1880’s Crossroads Village decked in holiday greenery, full of homes and shops bustling with holiday preparations. Treat yourself to a warm cup of wassail, do some holiday shopping, and see the largest Yule Goat in North America. Then, enjoy a horse-drawn ride around the village, but keep a watchful eye out for the Krampus! Meet 19th-century Santa for your one-of-a-kind holiday photo. Storytelling, holiday characters, sleigh rides, and more.
An Old World Christmas Website
Waukesha’s Annual Christmas Parade – Waukesha
December 8
The Corners of Brookfield
The City of Waukesha’s 61st Annual Christmas Parade is back this year with a Home for Christmas theme.
Canadian Pacific Holiday Train
November 19 – December 21
The CP holiday train is back! Holiday Train shows are free to attend. CP asks attendees to bring a cash or non-perishable food donation if they’re able. Local food shelves will set up collection stations at each event, with all donations made staying with the local food bank to help people in need in the community. Stops are in Wauwatosa, Hartland, Oconomowoc, Watertown and Columbus.
Canadian Pacific Holiday Train Schedule
Hanukkah Activities in our Community
This is just a sampling of the activities in our community. Check out this post to see them all!
What else needs to be on this list? We would love to hear about your favorite family holiday events!
Milwaukee Holiday Content
Greetings! I’m writing to let you know about a fun event that could be added to your list! ‘Bing Crosby Christmas on the Air’ is a musical, “live radio” style theatrical production happening this Holiday Season at the Historic Brumder Mansion. It is written and being performed by local Musician/Actor Matt Zembrowski and other local actors from December 8th-23rd and would be a pleasant intergenerational activity for families to attend together!
More info is at this website: http://milwaukeeentertainmentgroup.com/bing_crosby_christmas_on_the_air-2
Thanks for your consideration and for putting together this wonderful list!