18 Holiday Events in Milwaukee This Season

18 Holiday Events in Milwaukee This Season

Sleigh bells ring, are you listening? These are the holiday events of the season!

1. Enchant Christmas

NOW-DEC. 31  | FRANKLIN FIELD 

This holiday extravaganza features a light maze, ice skating trail, shopping village, visits with santa and plenty of activities for kids. 

2. A Christmas Carol

NOW-DEC. 24 | THE PABST THEATER

Enjoy the seasonal classic following Scrooge through his Christmas Eve, where he discovers that it’s never too late for redemption with the help from the ghosts of Christmas past, present and future. Beautiful music, dance, costumes and scenery help tell this timeless tale. 

Milwaukee Repertory Theater presents A Christmas Carol in the Pabst Theater November 30 – December 24, 2021. Pictured L-R: Michael Kostreva, Paxton Haley, Gabriela Bastardo, Lee E. Ernst, Ruth Ohlendorf, Ziva Lavoe and Quinn Sison; Photo by Michael Brosilow.

Tell us who you’d pick to be a Betty this year!

 

3. The Best Christmas Pageant Ever 

NOW-DEC. 24  | MARCUS CENTER

This family-friendly musical follows the horrible Herdmans – “the worst kids in the history of the world”– when they’re cast in the church’s annual Christmas pageant. The entire town has to discover the meaning of Christmas to save the performance. 

Maya O’Day Biddle (center) and cast in THE BEST CHRISTMAS PAGEANT EVER: THE MUSICAL. First Stage, 2023. Photo by Paul Ruffolo.

4. Rivoli Holiday Film Festival

DEC. 1-23, VARIOUS TIMES | RIVOLI THEATER CEDARBURG

The historic Rivoli theater will be showing a classic holiday movie (sometimes more than one!) every day from December 1st through the 23rd. Why not get your holiday movie fix in a classic single-screen theater with some theater popcorn rather than binging them at home?

5. Christmas in the Ward

DEC. 1 FROM 5:30-8:30 P.M. | CATALANO SQUARE

Kick off the season with festivities under the Historic Third Ward’s Christmas tree, including live entertainment and fireworks, photos with Santa and his reindeer, and local eats from on-site food trucks.

6. Santa’s Christmas Cavalcade

DEC. 2 AND DEC. 8 AT 5 P.M. | DOWNTOWN MILWAUKEE

See Santa and Mrs. Claus ride atop a vintage firetruck down the festival route starting at the public market. Sarah Fierek will be riding alongside them singing holiday tunes.

7. West Allis Christmas Parade

DEC. 2 | 81ST ST. STATE FAIR PARK ENTRANCE, EAST ON GREENFIELD AVE. TO 70TH STREET, THEN SOUTH TO ORCHARD AVE. 

This annual night parade features marching bands, live performers, floats and vintage vehicles. Meet Elves and wave Santa off at the end of the parade line. 

8. Holidays On The Hop

DEC. 2, 9 AND 16 FROM 3-5 P.M. | DOWNTOWN MILWAUKEE 

Holidays on the Hop continues this year to bring holiday cheer to downtown Milwaukee. There will be live musical performances on the streetcar, free cookies and festive decor. The Dec. 2 rides will feature the JL Russell Jazz Trio, Dec. 9 will have Sarah Fierek singing onboard and Dec. 16 will welcome the Milwaukee Choristers on the streetcar. 

9. Home For The Holiday’s at Old World Wisconsin

DEC. 2-3, 9-10 AND 16-17  | W372 S9727 WI-67, EAGLE

Drive just an hour outside of Milwaukee but travel hundred’s of years back in time. Walk through the 19th century-themed village with historic shops and homes decorated with festive greenery and holiday cheer. There will also be craft-making, parties and wagon rides. 

10. Breakfast With Santa

DEC. 3 FROM 9 A.M. -1 P.M. | THE STARLING 

Enjoy a delicious classic breakfast of pancakes, eggs, sausage and bacon alongside specialty Christmas donuts. Each purchase includes a photo with Santa!

11. Haunted Holidays Tour 

DEC. 8-9 AND 15-17 FROM 5 -10 P.M. | THE RAVE/EAGLES CLUB 

The said-to-be-haunted music venue will be decorated with both Halloween and Christmas decor for a self-guided tour that ends in the famed haunted pool. All guests will receive a holiday beverage with the tour. 

12. The Nutcracker

DEC. 8-26 | MARCUS CENTER

A brand new interpretation of the classic ballet show is in Milwaukee for the holidays. The performance will feature updated choreography, enchanting costumes and grand sets will allow you to experience the favorite holiday tradition anew.

13. Santa’s Dash Away 5K

DEC. 9 AT  8 A.M. | DOWNTOWN CEDARBURG

Help keep Santa’s workshop going strong in downtown Cedarburg by participating in the 9th annual Santa’s Dash Away 5K. All proceeds go to A Cedarburg Christmas which funds the Santa’s Workshop, a charming gingerbread house in the downtown area. Stop by to see the toys he’s working on and possibly even meet Mr. and Mrs. Claus.

14. JCC Community-Wide Hanukkah

DEC. 11 FROM 4:30-6 P.M. | HARRY & ROSE SAMSON FAMILY JEWISH COMMUNITY CENTER

The Jewish Community Center has partnered with local synagogues and Jewish organizations to put on this celebration that will feature a variety of projects, crafts, activities, food and entertainment. 

15. Cedarburg Chanukah Walk

DEC. 12 FROM 4:30-6 P.M. | JEWISH DISCOVERY CENTER

Come along for the Jewish Discovery Center’s first Chanukah walk in downtown Cedarburg. Local participating businesses will have festive surprises, and you can take a break from waking and ride with Judah Maccabee on the Chanukah trolley. The walk concludes with the grand Menorah lights in front of city hall, fire jugglers and a marching band. 

16. Experience the Spirit of Ujamaa: Pre-Kwanzaa Workshop With CLAWW

DEC. 17 FROM 3-6 P.M. | ST. FRANCIS OF ASSISI 

Join CLAWW for a workshop to embrace the spirit of Ujamaa with a day of food, fun and entertainment. Speakers will share tips on improving economic knowledge, there will be captivating drum and dance performances and a marketplace will be on-site to purchase specialty items and win raffle prizes. 

17. Happy Kwanzaa: Kids Arts and Crafts Party

DEC. 26 FROM 12-1 P.M. | VIBEZ CREATIVE ARTS 

Join Vibez for an hour of fun arts and crafts and celebration in the spirit of Kwanzaa. Kids will have fun while learning about the holiday. 

18. TSO: The Ghosts Of Christmas Eve 

DEC. 27  AT 3 AND 7:30 P.M. | FISERV FORUM

What bands do you think of when you think of holiday music? If you’re a rock fan, we’re sure the Trans-Siberian Orchestra is one that comes up a lot. Their winter tour this year will follow “The Ghosts Of Christmas Eve” tradition, a show that has captured the attention of generations while promising a larger presentation for this year.