Milwaukee Holiday Events & Festivals

When you need to experience that holiday spirit firsthand, there is nothing like a holiday festival! While things will look different this year, these events around the Milwaukee area are guaranteed to put you in a festive mood and create lasting memories for you and your family. 
The team at Milwaukee Mom is working hard to remain your go-to spot for parenting resources in the Greater Milwaukee Area. While we will do our best to be as up-to-date as possible, please be aware that we are still dealing with changes related to the COVID-19 Pandemic. Please consult your local public health authority for social distancing recommendations and call ahead to confirm hours and offerings of any business or organization listed. 

winter and holiday festivals

Milwaukee Holiday Events and Festivals

Celebrate the Holidays at Jelly Belly – Pleasant Prairie
Canceled for 2020. Check back in 2021. 
Jelly Belly Factory

A Christmas CarolMilwaukee
December 1 – December 24, 2020
In your home from The Pabst Theater!

While we might not be able to have in-person performances this year, we will not let 2020 cancel Milwaukee’s favorite holiday tradition! We know how much A Christmas Carol means to generations of Wisconsinites and at the end of a very difficult year, we are going to spread more holiday joy than ever before with the support of Wells Fargo and Jay Franke & David Herro.

This year only – we will have two full productions of Dickens’ timeless tale available to stream worldwide.

These are two fully realized productions (not Zoom readings) recorded professionally. Your experience watching these incredible shows from home will be as close as possible to watching live from the best seats in the theater. You can support our virtual holiday productions by purchasing a ticket and/or via a tax-deductible donation to our Rep Rising Emergency Relief Campaign, which helps keep our artists and staff employed as we head into our ninth month of being closed due to COVID-19.

Milwaukee Holiday Lights Festival – Milwaukee
November 19, 2020 – January 1, 2021
Downtown Milwaukee

Are you ready for a “snowcially-distanced” celebration? It’s the most dazzling time of year downtown – the Milwaukee Holiday Lights Festival is returning for its 22nd year!  Check out their website to download the 2020 Milwaukee Holiday Lights Festival Guide.

Holiday Folk Fair – West Allis
November 20th – November 22nd
Online from the comfort of your own home!

The 2020 Holiday Folk Fair International, originally scheduled for Friday, November 20 through Sunday, November 22, will not take place “in-person” at the State Fair Park Exposition Center. Rather, you can enjoy our online event from wherever you are, with many performances, demonstrations, and presentations from some of your favorite festival participants. The content will be placed online on Friday, November 20, as Folk Fair will officially begin that day.

Ten Days of Cheer – Brookfield 
November 27th – December 6
The Corners of Brookfield

We are celebrating the most wonderful time of the year with 10 Days of Cheer! Each day from November 27th through December 6th we will be making The Corners merry and bright with holiday shopping, twinkly lights, and exclusive offers to kick off the holiday season! Stay tuned for more details!

Every day, be dazzled by the lighting installation in Market Square, featuring a 40-foot lighted tunnel! Check their website or the Facebook event for a list of daily activities.

Tree Lighting - Corners of Brookfield

Waukesha’s 58th Annual Christmas Parade – Waukesha
Canceled for 2020.

Thank you to everyone that was excited about Waukesha’s Annual Christmas Parade. It is with great disappointment that the Chamber of Commerce has decided to cancel this year’s parade. Our decision is due to the rapid spread of Covid-19, and the record number of cases being recorded daily.  The City of Waukesha Chamber of Commerce has decided to use an “abundance of caution” for all involved, which includes both participants and parade watchers.

We look forward to celebrating our traditional holiday parade next year for the city’s 125th anniversary!

The Pfister Annual Tree Lighting Ceremony – Milwaukee
Canceled for 2020

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.

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
Canceled for 2020

The Board of Directors of the German Christmas Market of Oconomowoc have made the difficult decision to cancel the 2020 market.  With all the uncertainty, we are unsure of what the market would need to look like, and if social distancing were still in place, it is far too difficult for us to monitor.  We are entirely a volunteer group, and rely heavily on volunteers during the event itself, and do not feel we can keep our volunteers, the community, vendors and board members safe in an event such as this.

The 2021 event will be our 10th anniversary, and we are already making plans for some new and very special additions to the event, so stay tuned, and we hope to see you in 2021.

Milwaukee Makers MarketMilwaukee
November 28th, 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. The market is free but admission is required if you would like to visit the rest of the museum.

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. While you can’t Santa in his workshop this year, you CAN run in Santa’s Dash Away 5K on December 12th, enjoy the numerous craft fairs and art exhibits, or take a horse-drawn sleigh ride!

Jellystone Park’s Christmas Carnival of Lights – Caledonia
November 21st- December 31st, 2020
Yogi Bear’s Jellystone Park

No worrying about keeping your kids 6′ away from others, as you will be safely inside your car the whole time! 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 if you choose to pay at the entrance, you will need CASH. 

Country Christmas – Pewaukee
November 27th-January 2, 2021. Closed to the public on December 3.
Ingleside Hotel

Celebrating our 25th 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.


Canadian Pacific Holiday Train –
December 12th- Online

Join us and watch the live premiere concert ‘Holiday Train at Home’ on CP’s Facebook page on December 12 at 6 p.m. MT, and if you can, please give a little bit to support those in need!

We’ll be posting the final concert details on our social channels in the coming weeks so make sure you stay tuned to @CanadianPacific for the latest updates.

Serena Ryder and The Trews are headlining CP’s 2020 “Holiday Train at Home” concert with special guests JoJo Mason, Logan Staats, and Kelly Prescott.

4th Annual Christkindlmarkt – West Allis
Canceled for 2020.
West Allis Farmers Market

The City of West Allis Events Committee and Christmas Parade Subcommittee today announced the cancelation of the City of West Allis Christmas Parade, scheduled for Saturday, Dec. 5, and Christkindlmarkt, scheduled for Dec. 4 and 5 of this year. The City’s Tree Lighting Ceremony, scheduled for Saturday, Dec. 5, will not be open to the public but will be live streamed for viewing at home on the City’s social media.

Christmas in the Ward – Milwaukee
All December long
Third Ward

As you can guess, Christmas in the Ward presented by PNC will be a bit different than years past. The beautiful Christmas tree will be decorated and lit in Catalano Square (great selfie opportunities abound!) for all of December. Show your support and spread holiday love through the neighborhood. Help keep the Historic Third Ward’s businesses alive and thriving in the colder months ahead!

Midnight Magic – Mukwonago
December 5th, 10:00 AM-Midnight

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
Canceled for 2020.

The City of West Allis Events Committee and Christmas Parade Subcommittee today announced the cancelation of the City of West Allis Christmas Parade, scheduled for Saturday, Dec. 5, and Christkindlmarkt, scheduled for Dec. 4 and 5 of this year. The City’s Tree Lighting Ceremony, scheduled for Saturday, Dec. 5, will not be open to the public but will be live streamed for viewing at home on the City’s social media.

Breakfast and Lunch with Santa – Milwaukee
Canceled for 2020.
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 – Pandemic Edition – Franklin
Wehr Nature Center

Did you know that crafting helps reduce stress? Concentrating on the task at hand focuses the mind and reduces negative thoughts. Sadly, some of our favorite things have not happened this year due to the pandemic – we won’t let it stop Homemade Holidays! Crafts come ready to assemble and designed for your age group – we have gathered the recycled materials for you! These projects help children develop fine motor skills, self-esteem, focus and creativity by reusing and repurposing objects all while saving more “stuff” from going to the landfill! Depending on your choices, all you may need is a hammer, school glue or a glue stick to complete the project.

An Old World Christmas – Eagle
Canceled for 2020. Check back in 2021. 
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
Brady Street

We are currently still planning for the 2020 Festivus celebration in December. However, we are monitoring the COVID-19 situation and will announce any change in plans when necessary. Please check back for updates!

Breakfast with Santa at The Pfister – Milwaukee
Canceled for 2020. Check back in 2021.

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.

Pfister Holiday Marketplace – Milwaukee
Canceled for 2020. Check back in 2021. 

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 20th, 9:00AM-4:00PM
Wehr Nature Center

Citizen Science help needed! We will be counting wintering birds at Wehr Nature Center, as well as many other sites within the southern half of Milwaukee County. You’ll meet some talented and persistent birders as we observe birds in the most important and longest-running nationwide bird count. This count contributes to long-term population trends data. Register by December 18th. 

Christmas Celebration Brunch at The Pfister – Milwaukee
December 25th, 11:00AM-2:00PM

Don’t want to go out? You can order your at-home Christmas feast 48 hours in advance! 

Waukesha Janboree – Waukesha
2021 Dates not yet announced. Check their website for updates. 
Downtown Waukesha

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

Milwaukee 11th Annual Chili Bowl – Milwaukee
2021 Dates not yet announced. Check their website for updates. 
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
Winter Festival 2021 is Canceled. Check back in 2022! 
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!

Hanukkah is going to look different this year in our community. Community calendars have very few activities for Hanukkah. Here I’ve compiled what I could find and also listed some other resources for celebrating Hanukkah at home.

Every Night December 10-18

Menorah Lighting each night at 6:00 pm outside of the store Yellow Wood at 401 E Silver Spring Drive, Whitefish Bay courtesy of the JCC and Merchants of Whitefish Bay.

Community-wide Virtual Hanukkah celebration that will take place the entire 8 days of Hanukkah. It will be “located” on a central FB group where people can opt-in. Details to come.

Tuesday, December 9

 Chanukah Skating Party and Hot Dog Dinner 5:00-7:00 pm at Ozaukee Skateland 7084 Sycamore Drive, Cedarburg. There will be a Huge Hot Dog Bar with more than 20 choices of toppings! Latkes, prizes, and Chanukah gelt. Special Menorah Lighting at the Center of the Rink. Skaters: $15.00, Non-Skaters $10.00. Organized by the Peltz Center for Jewish Life

Wednesday, December 10

Grand Menorah Lighting 5:00-6:00 pm at Friendship Circle of Wisconsin, 8649 N. Port Washington Road, Fox Point. Hosted by The Shul Center and The Friendship Circle

Saturday, December 13

3:00-5:00 pm Over 100 cars lead by a giant Menorah display will parade on wheels starting at the Chabad of Mequon and the Shul Center, passing the Chabad Lubavitch Torah Center, the Lubavitch House and ending at the Fiserv Forum Plaza for a public Menorah lighting. See for more details. Organized by Chabad-Lubavitch of Wisconsin

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


  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:

    Thanks for your consideration and for putting together this wonderful list!


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