Save This For Later
We'll email this post to you, so you can come back to it later!
Santa Claus is making it easy for Milwaukee kids to send their holiday wishes straight to the North Pole! This season, you’ll find his bright red mailboxes popping up all around the city, ready to collect letters and wish lists.
Gather your little ones, get those lists ready, and spread some holiday cheer by dropping them off at one of these magical locations.
For even more ways to celebrate the season, check out our Holiday Fun Guide for a complete list of festive activities around Milwaukee.
Cathedral Square Park
📍 520 E. Wells St., Milwaukee, WI 53202
📅 November 10 – December 14, 2025
Downtown has a magical connection to the North Pole right in Cathedral Square Park. Drop your child’s letters and wish lists into Santa’s Mailbox to receive a personalized reply from the big guy himself! No postage required. Just remember to include a return address.
While you’re there, don’t miss Community Spirit Park, part of the Downtown Milwaukee Holiday Lights Festival.
Cheer District (Deer District)
📍Deer District Plaza near Fiserv Forum
📅 November 21st – 30th, 2025
There will be a Santa’s Mailbox in the Deer District this year, as well as a new Christmas Market with local vendors and live entertainment, reindeer, holiday music, and more. Don’t miss the City of Milwaukee Christmas Tree Lighting on November 21, 2025.
The Pfister Hotel
📍424 E. Wisconsin Ave., Milwaukee, WI 53202
📅 TBD for 2025
Write Santa a letter and drop it off in our magical North Pole Mailbox at the Front Desk. They’ll make sure it’s delivered in time for Christmas. Each child will receive a cookie and a personalized note from Santa himself!
While you’re here, make it a special outing by experiencing An Afternoon Tea Adventure at The Pfister: A Fancy Outing with Kids – a perfect addition to your holiday visit!
Milwaukee Public Market
📍400 N Water St, Milwaukee, WI 53202
📅 2025 Dates Coming Soon
Head up to the second floor of the Milwaukee Public Market to find a bright red mailbox that sends letters directly to the North Pole!
While you’re there, don’t miss the charming display of Gingerbread Houses crafted by MATC baking students. And, of course, warm up with a cup of hot cocoa from one of the market’s vendors.
Pabst Mansion
📍 2000 W. Wisconsin Ave., Milwaukee
📅 2025 Dates Coming Soon
Write a letter to Father Christmas at the Pabst Mansion, and he’ll even write back! Letters can be dropped off at the mansion during its holiday events. While you’re there, don’t miss the chance to explore their beautifully decorated rooms and meet Father Christmas in person every Sunday from 3:00 to 5:30 p.m.
Allis in Winterland
📍 City Hall Art Gallery, West Allis
Step into the magic of the season at the annual Allis in Winterland! The City Hall Art Gallery transforms into a cinematic holiday wonderland with festive decorations, fun activities, and even character visits to bring the beloved movie to life.
Be sure to bring your holiday wishes—North Pole mailbags will be ready to deliver your letters straight to Santa!
Country Christmas
📍 2810 Golf Rd, Pewaukee, WI 53072
Find this magical mailbox in Christmas Village at the Ingleside Hotel. It shows an animated scene of the letter flying to the north pole once the child places the letter in the mailbox. Letters to Santa are answered by elves if they choose to leave an email address.
The Corners of Brookfield
📍 20111 W. Bluemound Rd., Brookfield, WI 53045
Kids can drop off their letters and wish lists to Santa in the North Pole mailbox at the Corners of Brookfield. The mailbox will be located in Market Square Escalator vestibule. Be sure to check out the Corner’s holiday decorations and events, too.
Natty Oaks
📍11505 W. National Ave., West Allis, WI 53227
This North Pole mailbox is out all year round in front of the Natty Oaks restaurant, and kids will get a personalized reply to their correspondence. During the holidays, Natty Oaks has Santa Chalets outside where you can visit with Santa or catch him as he’s walking through 12,000 square feet of Christmas lights. Eat fresh popcorn and grab a cup of hot cocoa or cider while you wait to see the big guy.
American Family Field
📍 1 Brewers Way, Milwaukee, WI 53214
📅 2025 Dates Coming Soon
Ensure Santa knows what’s on your wish list this year with the Brew Crew’s very own North Pole Mailbox.
Milwaukee Mitchell International Airport
📍 5601 S. 6th St., Milwaukee, WI 53221
📅 2025 Dates Coming Soon
A special “Santa’s Mailbox” is back at Milwaukee Mitchell International Airport just in time for the holiday season! Passengers flying through Concourse D can drop off their letters December 1-8.The mailbox is near the clock tower on Concourse D.
Santa’s Workshop
📍Washington Ave., Cedarburg, WI 53012
Each year, a charming 15×15-foot gingerbread house graces Cedarburg’s Washington Avenue for the entire Christmas season. Santa and Mrs. Claus will be stopping by Santa’s Workshop on select days. Kids are encouraged to drop off letters to Santa.
Whitefish Bay
📍316 E. Silver Spring Dr., Whitefish Bay, WI 53217
The Merchants of Whitefish Bay have a direct connection to the North Pole, so they know Santa will get each letter that’s dropped off in this mailbox.
You can catch a glimpse of the man in red himself in the Holiday Stroll parade down Silver Spring Drive, taking place the Friday after Thanksgiving.
Mequon Public Market
📍6300 W. Mequon Rd., Mequon, WI 53092
📅 2025 Dates Coming Soon
Trees For Less
📍11550 N. Wausakee Rd., Mequon, WI 53097
Trees for Less is a full-service Christmas Tree farm with beautiful fresh cut Christmas trees, wreaths, porch pots and gnomes. Plus, their farm offers a full family experience including pictures with Santa, hayrides, hot cocoa, snacks and a roaring bonfire.
A special highlight: Santa’s Mailbox is located right next to Santa’s sleigh, giving kids a magical place to drop their letters to Santa.
Colectivo Coffee
📍 TBD
📅 2025 Dates Coming Soon
And if your little ones are eager to meet Santa in person, don’t miss our guide to the Best Places to Meet Santa this holiday season!
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.
