Milwaukee Holiday Events & Festivals

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When you need to experience that holiday spirit firsthand, there is nothing like a holiday festival! These events around Milwaukee area guaranteed to put you in a festive mood and create lasting memories for you and your family. 

Milwaukee Holiday Events and Festivals

Celebrate the Holidays at Jelly Belly – Pleasant Prairie
November 16th, 5:30 pm to 8:00 pm
Jelly Belly Factory

Kick off the Christmas season at the Annual Jelly Belly Christmas Tree Lighting. Ceremony begins at 6:00pm followed by photos with Santa Claus. Extended store hours, free samples, face painting, balloon art.


A Christmas CarolMilwaukee
November 26 – December 24, 2019
The Pabst Theater

A Milwaukee holiday tradition! The Rep’s hit adaptation is a tale of love, hope and redemption with just the right blend of beautiful music, lively dancing, stunning sets and eye-popping visual effects. It’s a dazzling Christmas feast with enough theatrical goodies to fill any sized stocking hung by the chimney with care. Join Bob Cratchit, Tiny Tim and, of course, Scrooge in this holiday classic the whole family will love.


Milwaukee Holiday Lights Festival – Milwaukee
November 21st, 2019 – January 1st, 2020
Downtown Milwaukee

It’s the most dazzling time of year downtown – the Milwaukee Holiday Lights Festival is returning for its 21st year! Kick off the season on Thursday, November 21 at Pere Marquette Park with a holiday variety show and the city’s largest switch-flipping ceremony. Check back for more information on this year’s festival.


Holiday Folk Fair – West Allis
November 22nd – November 24th
Wisconsin State Fair Park Expo 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.


Lighting of The Corners – Brookfield
November 23rd

You’re in for a tree-mendous celebration Saturday, November 23rd! It’s our third holiday season at The Corners, and we are going BIG! Help us get in the holiday spirit & join us for our third annual Tree Lighting Ceremony at The Corners of Brookfield. FREE to the public!

Meet Santa & his reindeer, here from the north pole! Enjoy a spectacular tree lighting in Market Square, live holiday music from local favorites, and much more!

Tree Lighting - Corners of Brookfield


Waukesha’s 57th Annual Christmas Parade – Waukesha
November 24th, 4:00PM

​Join the City of Waukesha Chamber of Commerce for a magical Main Street Christmas parade.


The Pfister Annual Tree Lighting Ceremony – Milwaukee
November 29th, 5:00-6:30PM

Join The Pfister Hotel for their 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.  HungerTaskForce.org

To support those in need during the holiday season, The Pfister Hotel will collect food for the Hunger Task Force and encourages guests to bring non-perishable food items. This event is free and open to the public. Enjoy complimentary parking with any purchase.


German Christmas Market – Oconomowoc
November 29th-30th, December 1st

Experience Authentic European Food & Drink, Unique Shopping Opportunities, Live Polka Music and Much More! Bring the entire family or plan to meet up with friends.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!

Milwaukee Makers MarketMilwaukee
November 30th, 10:00AM-4:00PM
Discovery World

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. Explore the market, have fun, meet amazing artists and artisans, shop, and support independent maker spirit in Milwaukee.


A Cedarburg Christmas – Cedarburg
Mid-November 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. Make a visit to Santa in his workshop, run in Santa’s Dash Away 5K on December 16th, enjoy the numerous craft fairs and art exhibits, or take a horse-drawn sleigh ride!


Jellystone Park’s Christmas Carnival of Lights – Caledonia
November 30th- December 31st, 2018
Yogi Bear’s Jellystone Park

Guests will be dazzled by new moving displays, and “Evy the Talking Christmas Tree,” a popular, animatronic, seven-foot character who made his debut last year and talks and sings to visitors of all ages. Evy will be located inside Santa’s Workshop, where guests can enjoy hot beverages and visit with Santa. Santa’s giant sleigh, which seats 43 guests in tiered and comfortable seating, will also travel through the light show and give families the opportunity to experience the show in a whole new way. Reservations to ride on the sleigh may be made at wichristmascarnival.com/book-a-sleigh-ride.


Country Christmas – Pewaukee
November 29th-December 1st and December 6th-December 31st
Ingleside Hotel

Celebrating our 24th year as Wisconsin’s largest and most spectacular drive-through holiday lights display ! As part of admission to Country Christmas, you can experience the Country Christmas Trail, Christmas Village, and the Streets of Bethlehem. Click on the photos below for more information.

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Canadian Pacific Holiday Train – Wauwatosa, Hartland, Oconomowoc, Watertown
December 3rd – Location times vary

The Canadian Pacific (CP) Holiday Train will set out once again to entertain hundreds of thousands of people, celebrating 21 years of collecting food and raising funds for food banks across North America. This year the local stops include Wauwatosa, Hartland, Oconomowoc and Watertown.

The train will arrive at the scheduled event time for each location and depart immediately after the show. Please give yourself extra time getting to the event to compensate for crowds and traffic.


3rd Annual Christkindlmarkt – West Allis
December 6th-7th
West Allis Farmers Market

The Christkindlmarkt gets bigger, better and more festive each year. Join in sharing the holiday spirit and seeing why the Christkindlmarkt is a beloved holiday event! Be merry and shop a traditional European-style Christmas market featuring over 70 Wisconsin specialty food retailers and artisan craft vendors


Christmas in the Ward – Milwaukee
December 6th, 5:30-8:30PM
Third Ward

Fireworks, reindeer, horse-drawn carriage rides and Santa kick off a fabulous weekend of holiday shopping!


Midnight Magic – Mukwonago
December 7th, 10:00AM-10:00PM

Old fashioned Christmas celebration.  Town-wide festival featuring indoor crafter marketplace, shopping, parade, fireworks, pictures with Santa, holiday entertainment, horse drawn carriage rides, and more!


Annual West Allis Christmas Parade – West Allis
December 7th, 4:45PM-6:30PM

Bundle up, grab some hot chocolate and join us for the Annual West Allis Christmas Parade! This year’s theme is Lights, Camera, Christmas: Take 2! Enjoy marching bands, live performers, creative floats, vintage vehicles and more. See your favorite cartoon characters and wave to the big man himself, Santa Claus, at the end of the parade! Don’t forget to drop a letter for Santa off with one of his North Pole elves!


Breakfast and Lunch with Santa – Milwaukee
December 7th-8th, 14th-15th and 21st-22nd
Milwaukee County Zoo

Come to the zoo for holiday cheer and celebration as Santa and Mrs. Claus make their annual trip to the Milwaukee County Zoo to visit children for a special breakfast or lunch, featuring Racine Danish Kringle! Breakfast is served at 9 a.m. and lunch is at noon Saturdays and Sundays.

Breakfast with Santa - Zoo


Homemade Holidays – Franklin
December 7th, 11:00AM-3:00PM
Wehr Nature Center

The Wehr Nature Center invites you to bring your kids, grandkids, nieces and nephews, the neighborhood gang, or scout group to Wehr to create homemade treasures from natural, recycled and re-purposed objects. Make and take home three different projects for the admission fee. Projects include snow globes, coloring books & homemade crayons, bird feeders, troll rocks, a variety of holiday ornaments and more. Stop by anytime to make your works of art. Recommended for kids ages 5 and under.


An Old World Christmas – Eagle
December 7th-8th, 14th-15th
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.


Festivus – Milwaukee
December 7th, 3:00PM-1:30AM
Brady Street

The 4th Annual Festivus One Mile Run- 5,280 “Feats” of Strength at 3pm. All runners receive a pair of winter mittens, a beer at the half mile turn-around (located at Casablanca,) a finisher festivus pole medal, and a free beer at participating bars!


Breakfast with Santa at The Pfister – Milwaukee
Saturdays and Sundays, December 7th, 8th, 14th, 15th, 21st and 22nd
Two seatings each date: 8-9:30AM and 11:30AM-1:00PM

Back by popular demand, the Pfister Breakfast Buffet with Santa is a holiday tradition that creates lifelong memories. Guests have the opportunity to share a jolly breakfast collection with Santa and his elves in The Pfister’s festive ballroom.  They will have chefs in the room griddling up chocolate chip and blueberry pancakes with all the trimmings, along with everyone’s traditional buffet favorites. In addition to photos with Santa, which are highly encouraged, every child will receive a special gift and will be able to make crafts while composing a hand written letter to Santa. Smaller seating groups for each date will ensure that everyone has an exceptional experience.


Pfister Holiday Marketplace – Milwaukee
December 14th-15th, 10:00AM-5:00PM

Experience and enjoy the majestic Holiday ambiance of the Pfister Hotel lobby while interacting and connecting with over 60 local artists and vendors. The perfect place to find the perfect gifts; all while taking in the sights and sounds of local music and art! 15 guest rooms on the mezzanine level will be mini pop up shops, each designed by a local vendor. 20 new vendors each day in the hallway – so be sure to stop by both Saturday and Sunday to see them all.


Christmas Bird Count – Franklin
December 15th, 9:00AM-4:00PM
Wehr Nature Center

Join Wehr Nature Center, and other sites across the southern half of Milwaukee County, to count wintering birds. You’ll meet some talented and persistent birders as you observe birds in the most important and longest-running nationwide bird count. This count provides important information on long-term trends. Chili and fixin’s provided at Wehr; you are welcome to bring other food to share.


Christmas Celebration Brunch at The Pfister – Milwaukee
December 25th, 11:00AM-1:30PM


Waukesha Janboree – Waukesha
January 17th-26th, 2020
Downtown Waukesha

From families, to adults, to children, there’s fun for everyone. Get to the Waukesha JanBoree!


Milwaukee 11th Annual Chili Bowl – Milwaukee
January 26th, 2020
Potowotomi Hotel & Casino

At Wisconsin’s largest chili cook-off, Milwaukee’s top chefs and restaurants will compete for Milwaukee’s best, sampling more than 60 varieties of chili, but only one will leave with the Golden Ladle award. Reserve your tasting ticket and you’ll be able to sample traditional and spicy chili, along with specialty chili like chicken, lamb, brisket, sweet potato, bratwurst, and vegetarian chili.


Cedarburg Winter Festival – Cedarburg
February 15th-16th, 2020
Downtown Cedarburg

Ice sculpture contest, chili cook-off, snowball tournament, camel rides and petting zoo, shops at Cedar Creek Settlement, crafts, marketplace, food and so much more!


Hanukkah Activities in our Community

This is just a sampling of the activities in our community. Check out this post to see them all!

Monday, Dec. 16
4 pm – 6:30 pm, Harry & Rose Samson Family JCC (6255 N Santa Monica Blvd)
Community Wide Chanukah Party
For more information contact, Rabbi Shari Shamah ([email protected])

Tuesday, Dec. 17
5:30 pm – 7:15 pm, Milwaukee Jewish Day School (6401 N Santa Monica Blvd)
MJDS Chanukah Pajamakah
For more information, contact Michal Deskalo ([email protected])

Saturday, Dec. 21
7:30 pm, Congregation Sinai (8223 N Port Washington Rd)
Hanukkah Latke & Whiskey Tasting
For more information, contact Sam Pollock ([email protected])

Sunday, Dec. 22
6 pm – 8 pm, Congregation Beth Israel Ner Tamid (6880 N Green Bay Ave)
Hanukkah Dinner
For more information, contact Marlynn Brick ([email protected])

Monday, Dec. 23
5 pm – 7 pm, Ozaukee Skateland (7084 Sycamore Dr, Cedarburg)
Peltz Center for Jewish Life Chanukah Skating Party & Hot Dog Bar
Skaters: $15, Non-Skaters: $10
For more information, call 262-242-2235

Wednesday, Dec. 25
12 pm – 3 pm, Jewish Museum Milwaukee (1360 N Prospect Ave)
Annual Christmas Cinema: Houdini (1953)
Screening begins at 1 pm
Regular Museum Admission Applies, Members Free
For more information, call 414-390-5730

Thursday, Dec. 26
4 pm – 7 pm, Jewish Museum Milwaukee (1360 N Prospect Ave)
Lake Park Synagogue Chanukah Celebration
For more information, call 414-962-5508

Saturday, Dec. 28
5 – 8:30 pm, UW Panther Arena (400 W Kilbourn Ave)
JCC Hanukkah with the Admirals
For more information, call 414-964-4444

What else needs to be on this list? We would love to hear about your favorite family holiday events!

1 COMMENT

  1. 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!

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