10 Best Places to Meet Santa This Year (2023)

Santa Claus has landed safely in Milwaukee!

We’re keeping track of all the stops he’s making around Southeastern Wisconsin.

Here’s a running list of the best places you can meet Santa this year:

1. Cocoa with the Clauses (Free!)

Sat, December 9, 2023 11am to 2pm Cathedral Square Park
414.220.4700 | milwaukeeholidaylights.com

Santa and Mrs. Claus return for this annual cocoa klatch. The free outdoor event is a chance for kids to share their wish lists and for moms and dads to grab a keepsake photo. 

Elves and other holiday characters will also be there! Plus, complimentary cookies and hot cocoa sponsored by Taste of Home will be provided.

2. Santa’s Christmas Calvalcade (Free!)

Sat, December 2, 2023 | Departs at 5pm
Fri, December 8, 2023 | Departs at 5pm
Downtown Milwaukee

Wave to Santa and Mrs. Claus on the festive route riding atop a vintage fire truck. Sarah Fierek will also be on board singing jazzy holiday tunes.

On Dec. 2, the Cavalcade will feature a Black Santa.

The route departs from the Milwaukee Public Market and travels throughout downtown.

3. Father Christmas at the Pabst Mansion

With his lantern, walking stick and red cloak with white trim, a whimsical Father Christmas travels south to visit the Pabst Mansion each Sunday during the holiday season.

Create magical memories with holiday treats, letters to Santa, and room after room of enchanting Christmas displays.

4. Breakfast with Santa at the Pfister

December 9 & 10, 16 & 17, 2023

Back by popular demand, the Pfister Breakfast 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 handwritten letter to Santa. Smaller seating groups for each date will ensure that everyone has an exceptional experience.

Reservations required with full pre-payment by credit card. Reservations are refundable if canceled 72 hours prior to the event. 

5. Breakfast (and Supper!) with Santa at Saint Kate

Saint Kate – The Arts Hotel
December 16 & 17, 22 & 23

Start a new holiday tradition at Saint Kate’s “Brunch With Santa” and create lifelong memories! Guests will have the opportunity to experience a plentiful brunch in Saint Kate’s festive ballroom and visit with the jolly man himself.

There will be chefs in the room griddling up waffles with all the trimmings, along with traditional buffet favorites.

Supper with Santa
Sat, December 16 6pm to 7:30pm

Experience a magnificent dinner in Saint Kate’s festive ballroom, topped off with a visit from the jolly man himself!

In addition to the opportunity to take photos with Santa, every child will receive a special gift, and will be able to make crafts and write their own letter to Santa.

6. Brunch With Santa at Little Sprouts Play Café

Shorewood: 4606 N. Wilson Dr., Shorewood, WI​ 53211
Mequon: 1406 W. Mequon Rd., Mequon, WI 53092

Santa Claus is coming to…brunch! Little Sprouts is adding one more way to celebrate with Santa this year. Come enjoy open play, a brunch buffet, mimosas, coffee and Santa! He is also bringing a small gift for each child over 12 months. Parents are welcome to take their own photos of their kids with Santa.

This 90 minute playdate will include a brunch buffet including an array of brunch food, mimosas and coffee. There will also be plenty of time for open play and visiting with Santa. He will arrive sometime in the middle of the event and stay as long as needed to ensure all who want to chat and take pictures with him are able to do so. 

For a little added magic, your child can hand deliver Santa a list or letter. Have your child give it directly to Santa and they can discuss the contents during their visit. Santa will also be handing each child a small sack filled with some holiday goodies. 

Advanced registration required. Tickets are non-refundable. 

7. Natty Oaks Santa Chalet

11505 W. National Ave., West Allis, WI 53227
Beginning November 27th, 2023

Natty Oaks offers three cozy, clear-view Santa Chalets, so your family can have a fun, unique holiday experience. Each outdoor chalet seats up to six adults and features an adorable mini fireplace to keep everyone warm, even on a snowy night. Eat fresh popcorn and warm up with a complimentary carafe of hot cocoa or hot cider.

During your one-hour visit, you will get a special personalized visit from Santa! He will visit with your family for 15 minutes, providing the perfect opportunity to take photos and ask questions about the North Pole. An elf will be on hand to take photos for you (using your camera).

You can also catch the big guy himself as he’s walking through 12,000 square feet of Christmas lights displays around the property.

8. MOTOR Bar & Restaurant

Harley-Davidson Museum, 401 W. Canal St., Milwaukee, WI 53203
TBD for 2023

Bring the family for breakfast with Santa, then take part in an audio-guided experience that will dive into Harley-Davidson history, demos on H-D® IRONe™ (a kid-size electric balance bike), airbrush tattoos, LEGO kits and more.

Along with the usual lunch menu, a breakfast menu will be available. Gingerbread houses can be purchased to decorate for $20 each.

9. Sprecher Brewery

701 W. Glendale Ave., Glendale, WI 53209
Nov. 20, 27; Dec. 4, 11, 2022 (tours at noon, 1 p.m. and 2 p.m.)  
Admission: Adults $12, Minors $8

Sprecher Brewery Soda With Santa Claus photo Glendale Wisconsin

Soda with Santa is a time-honored tradition and a fun, family-friendly event at Sprecher Brewery! On Sundays during the holiday season, you can get your photo taken with Santa, then go on a brewery tour with craft beer samples for the adults and unlimited soda samples for everyone.

You can start getting samples after check-in, so you can enjoy beer or soda while you wait for your picture.

While you’re on the tour, Sprecher uses your Santa picture to create a custom label (choose from two designs. Then they put that label on as many 12-packs of 16 oz. Root Beer bottles as you choose to purchase (12 bottle minimum; $2.25 per bottle).

10. More Brunch With Santa Options:

Brunch With Santa at the Ingleside Hotel

Brunch With Santa at Cafe Hollander
TBD for 2023

Santa’s Mailbox

Downtown has a magical connection to the North Pole right in Cathedral Square Park. 

From November 7 through December 17, drop your child’s letter and wish list into Santa’s Mailbox to receive a personalized reply from the big guy himself! 

No postage is required; just remember to include a return address.

Letters to Santa at the Pfister

Write a letter to Santa and drop it off at The Pfister Hotel North Pole Mailbox. Each child will receive
a personalized note from Santa himself, plus all children will receive a free cookie from the Pfister front desk when they drop off their letters.

Do you know where Santa will be this year? Email us the information at hello@mkewithkids.com.

There’s more!

Experience Gift Ideas
Holiday Light Displays
Santa’s Mailboxes
Magical Holiday Experiences
Local Toy Stores
Sleigh Rides

Did you like this article?

Check out “101 Best Things to do in Milwaukee With Kids“.

About the author

In 2013, Calie Herbst, a former teacher with three little ones, saw a need for a “One Stop Shop” for family fun in Milwaukee. So she founded Milwaukee With Kids. Her goal was to find the best this city has to offer families and share it with other parents. In one place. In 2019, she published "Exploring Milwaukee WIth Kids", a comprehensive Milwaukee travel guide for families and kids. She appears regularly on WISN News, Fox 6's 'Real Milwaukee', B93.3, and Wisconsin Morning News. She has been featured in Medium, the Milwaukee Journal Sentinel, NPR, the Wisconsin Jewish Chronicle, and on CBS 58 News. Calie is available for hosting, moderating and media appearances.

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