Things to Do This Holiday Season in Milwaukee

There’s plenty to do this holiday season in Milwaukee. Check out our list of fun activities for kids and adults, too. Plan your weekend schedule now.

Art & Culture

Leonard Bearstein Symphony Orchestra
Nov. 14 – Jan. 2
If you have yet to see a pack of musically talented animals perform Christmas music in the middle of a shopping center, you have until Jan. 2 to watch 18 animatronic bears charm young and old audiences alike.

Grand Avenue Christmas
Nov. 18 – Jan. 8
Explore the festive opulence that adorns each and every room of the Pabst Mansion.

Holiday Treasures & Traditions Exhibition
Nov. 19 – Dec. 31
Travel back in time to celebrate Milwaukee’s annual Holiday Parade via decorations, photographs, relics and stories from years past.

Not a Creature Was Stirring – Holiday Floral Show
Nov. 19 – Jan. 1
Walk through the winter wonderland created in the beautifully lit show dome at the Milwaukee Park Horticultural Conservatory. Fir, pine and spruce trees serve as sanctuaries for forest critters while poinsettias procure holiday cheer.

Rudolph the Red-Nosed Reindeer: The Musical
Nov. 25 – Dec. 31
Join Rudolph and his pals in their quest to save Christmas as the cherished TV classic returns to the stage at the Todd Wehr Theater.

BMO Harris Bank Holiday Display
Nov. 28 – Jan. 2
Take in the sight of 150 life-size Steiff animals at BMO Harris Bank’s Holiday Display. For each visitor, BMO Harris will donate $5 to Feeding America Eastern Wisconsin. Free and open to the public.

A Christmas Carol
➸ Nov. 29 – Dec. 24 

Immerse yourself in the glow of the Christmas spirit with the most elaborate and technologically advanced adaptation of the production in Milwaukee to date.

MIAD Holiday Sale
➸ Dec. 1 – 3
Put down the hot glue gun and sift through scores of locally made gifts at MIAD’s holiday sale, with prices starting at $10.

The Wizards of Winter
Dec. 17
Featuring former members of the Trans-Siberian Orchestra, don’t expect the Wizards of Winter to perform traditional Christmas music; these progressive rock holiday tunes are anything but typical.

The Nutcracker
Dec. 10 – Dec. 27
It’s impossible not to be awestruck by the beauty and talent that the Milwaukee Ballet procures in The Nutcracker.

Kooky Cooky House
Mid-Nov. – Jan.
The original Kooky Cooky House, a chalet containing an enchanting cookie factory, brought joy to children from the ’60s through the ’80s. Create new memories at Discovery World’s recreation of the Milwaukee holiday favorite.


Hot Cocoa & Cookies in December in the Monarch Lounge
Mon. – Sat. in December
Sit back and relax with cookies and hot cocoa (add booze for an additional $5) in the cozy Monarch Lounge at the Hilton.

Ugly Sweater Party
Dec. 2, 9, 16 and 23
Don your favorite ugly sweater or bring one to donate to Kagel School and receive your first tap beer free of charge.

Christmas Around Milwaukee Bakery Bus Tour
Dec. 2 – 24
Try delicious holiday candies, cookies and pastries from some of the best bakeries in Milwaukee and enjoy tales of ethnic holiday traditions on the way.

Photo courtesy of Marcus Hotels & Resorts.
Photo courtesy of Marcus Hotels & Resorts.

Breakfast with Santa
Dec. 3, 10 and 17
Dine with Santa and his elves in the Pfister’s decorative ballroom, where each child will receive a special gift.

Christmas Lights & Desserts Tour
Dec. 3 – Dec. 23
Taste desserts and hot chocolate as you travel to one local restaurant to another by mini coach, enjoying the downtown lights on the way.

Christmas Eve at Milwaukee ChopHouse
Dec. 24
Enjoy Milwaukee ChopHouse’s scrumptious dinner menu along with the company of loved ones on Christmas Eve.

Glühwein & Sweets Special at CLEAR
Dec. 24
Sample desserts while you enjoy Glühwein (European mulled wine) at the InterContinental.

Photo courtesy of Marcus Hotels & Resorts.
Photo courtesy of Marcus Hotels & Resorts.

Christmas Day at Kil@wat
Dec. 25
Feast with family and friends on Kil@wat’s outstanding plated brunch.

New Year’s Eve with a View at Blu
Dec. 31
Ring in the New Year with an epic view of the Milwaukee skyline at Blu Bar and Lounge on the 23rd floor at the Pfister.

Photo courtesy of Marcus Hotels & Resorts.
Photo courtesy of Marcus Hotels & Resorts.

Outdoor Activities

Milwaukee Coach & Carriage
Marvel at the Christmas lights while riding a horse-drawn carriage through downtown Milwaukee.

Santa’s Mailbox
Nov. 18 – Dec. 11
Make your child’s dream come true! Deliver letters to Santa in his mailbox at Cathedral Square Park, then be on the look out for a personalized letter from ol’ Kris Kringle.

Jingle Bus Rides
Nov. 18 – Dec. 30
For just $1 per person, climb aboard the Jingle Bus to admire the holiday decor that adorns Milwaukee’s downtown while learning about the city’s landmarks.

Ideal Property Management, Inc. Christmas Tree Lot
Nov. 19 – Dec. 24
Breathe in that fresh pine scent while browsing Wisconsin Christmas trees, garland, wreaths and decorations at this old-fashioned tree lot.

Holiday Lights Walking Tour
Dec. 1 – Dec. 24
Play Christmas trivia and learn about the history of Milwaukee while you follow an elf through 1.25 miles of the city’s most beautifully decorated streets.

28th Annual Christmas in the Ward
Dec. 2 – Dec. 3
Get into the holiday spirit with a vast array of Christmas activities, including horse-drawn carriage rides, live holiday music and fireworks over the river.

Jolly’s Outdoor Gingerbread House
Dec. 2, 3, 9 and 10
Nibble on a cookie while you tell Santa what’s on your Christmas list at Jolly’s Outdoor Gingerbread House.

Santa Hustle 5K Milwaukee Run/Walk
Dec. 3
Throw your Santa hat on and grab your running shoes. Whether you choose to spectate or participate, you won’t want to miss the sight of thousands of Santas scurrying through Veterans Park.

CP Holiday Train
Dec. 5
Watch the Canadian Pacific Holiday Train, adorned with hundreds of thousands of holiday lights, pass through the Milwaukee Intermodal Station from 6:50 p.m. to 7:20 p.m.

Slice of Ice
Dec. 15 – March 2017
Bring your own skates or rent a pair at Slice of Ice, the downtown ice-skating facility in Red Arrow Park. Warm up with a hot drink at the Starbucks next to the ring.



Elisabeth Wallock is a contributing digital editor at Milwaukee Magazine. She graduated from Colorado State University and has interned at Marie Claire in New York and Urban Outfitters in London.